IAOe?IIAEUeIA AEAAeAI?ss IAOE OE?A?IE
?INOEOOO I?AAI?*II? O?I??
OAeE 547.544:547.78+547.87
OA?*AIEI
Ieaenaiae? Aaneeueiae/
CANOINOAAIIss S-AI?AeIAEE?ETHAAIIss
A NEIOACAO OOIEOe?IIAEUeIEO IIO?AeIEO ACIOENOEO AAOA?IOeEEE?A
02.00.03 – i?aai?/ia o?i?y
AAOI?AOA?AO
aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy
aeieoi?a o?i?/ieo iaoe
Ee?a – 1999
Aeena?oaoe??th ? ?oeiien.
?iaioa aeeiiaia ia eaoaae?? i?aai?/ii? o?i?? Oe?a?inueeiai aea?aeaaiiai
o?i?ei-oaoiieia?/iiai oi?aa?neoaoo (i. Aei?i?iiao?ianuee).
Iaoeiaee eiinoeueoaio:
aeieoi? o?i?/ieo iaoe, i?ioani?
Ae?a/ Ai?en Na?a?eiae/,
?inoeooo a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie,
caa?aeoaa/ a?aeae?eo o?i?? a?iaeoeaieo acioiai?nieo
aaoa?ioeeee?/ieo iniia
Io?oe?ei? iiiiaioe:
aeieoi? o?i?/ieo iaoe, i?ioani?
ssaoiieuenueeee Eaa Ion?eiae/,
?inoeooo i?aai?/ii? o?i?? IAI Oe?a?ie,
aieiaiee iaoeiaee ni?a?ia?oiee
aeieoi? o?i?/ieo iaoe, i?ioani?
Oeey Aieiaeeie? Iao?iae/,
Ee?anueeee iaoe?iiaeueiee oi?aa?neoao
?iai? Oa?ana Oaa/aiea,
caa?aeoaa/ eaoaae?e i?aai?/ii? o?i??
aeieoi? o?i?/ieo iaoe, i?ioani?
Aaiouae Ieeiea ?aaiiae/,
Euea?anueeee oi?aa?neoao ?iai? ?aaia O?aiea,
caa?aeoaa/ eaoaae?e i?aai?/ii? o?i??
I?ia?aeia onoaiiaa: ?inoeooo o?ceei-i?aai?/ii? o?i??
oa aoaeao?i?? ?i. E.I.Eeoaeiaiea IAI Oe?a?ie (i.Aeiiaoeuee)
Caoeno aeena?oaoe?? a?aeaoaeaoueny ” 16 ” a?oaeiy 1999 ?. i 14 aiaeei?
ia can?aeaii? niaoe?ae?ciaaii? a/aii? ?aaee Ae 26.217.01 i?e ?inoeooo?
i?aai?/ii? o?i?? IAI Oe?a?ie ca aae?anith: 253660, Ee?a-94, aoe.
Io?iainueea,5.
C aeena?oaoe??th iiaeia iciaeiieoenue a iaoeia?e a?ae?ioaoe? ?inoeoooo
i?aai?/ii? o?i?? IAI Oe?a?ie.
Aaoi?aoa?ao ?ic?neaiee ” 8 ” eenoiiaaea 1999 ?.
A/aiee nae?aoa? niaoe?ae?ciaaii? a/aii?
?aaee, aeieoi? o?i?/ieo iaoe, i?ioani?
Oauaiei I.A.
CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE
Aeooaeuei?noue oaie. ?ioaineaiee ?icaeoie o?i?? n??eiai?nieo i?aai?/ieo
niieoe (NIN) iaoiiaeaiee ?o aaeeeei iaoeiaei oa i?aeoe/iei cia/aiiyi.
Aeaye? c NIN ? iacai?iieie ia’?eoaie aeey aeine?aeaeaiiy ? ?ica’ycaiiy
caaaeueieo i?iaeai i?aai?/ii? o?i??, a ?io? iathoue oe?ii? aeey i?aeoeee
aeanoeaino?. Na?aae NIN ciaeaeai? aoaeoeai? ianoeoeeaee, iaaee/i?
i?aia?aoe, aa?aieee, ieth/? caniae, iiaeeo?eaoi?e oeaiei oa
noaa?e?caoi?e aeanoiia??a, ye? oe?iei canoiniaothoueny a ??cieo aaeocyo
ainiiaea?noaa. C?o/i? iaoiaee iaea?aeaiiy aaaaoueio NIN aaea ?ic?iaeai?,
aea i?aeoiaee aei iie?ooieoe?iiaeueieo NIN aeine?aeaeai? iaaeinoaoiuei.
Iniaeeai aaaeeeaeie ? iiooee iiaeo aeinooiieo n??eiai?nieo ?aaaaio?a c
e?eueeiia aeoeaieie oeaio?aie, ye? iiaeia aoei a aeei?enoaoe aeey
neioaco aaaaoueio iaa?aeiieo ?ai?oa oei?a aoeeee?/ieo oa
aaoa?ioeeee?/ieo NIN. Caeaaaeinue aeioe?eueiei aeei?enoaoe aeey ?o
iaea?aeaiiy i?iaeoeoe S-(-ai?aeiaee?ethaaiiy c oa?aeoa?iei o?aaiaioii
a yeiio – n??eiai?ni? ooieoe?iiaeuei? a?oie c ??ciith aaeaioi?noth aoiia
n??ee.
Ia a?aei?io a?ae aeia?a aea/aiiai ? aeineoue aaaeeeaiai
N-ai?aeiaee?ethaaiiy, ui ?icaeioeinue ye aa??aio ?aaeoe?? Iaii?oa,
S-(-ai?aeiaee?ethaaiiy, oi/a ? aoei a?aeiia aei ii/aoeo iaoeo ?ia?o a
na?aaeei? 80-o ?ie?a, ana ae oaee ia iaei oe?ieiai canoinoaaiiy aeey
i?aia?aoeaiiai io?eiaiiy NIN. A?aeii? aoee o?eueee neioace ia iniia?
oiceeiaoee?cii?o?eeo – niaoeeo?/iiai ?aaaaioo, ui eaaei io?eio?oueny c
oeiiaiai i?iaeoeoo S-ai?aeiiaoeethaaiiy – oiceeiaoeeoi?iai?aeo.
A?aeaeath/e iaeaaeia oeei ?iaioai, ye? c oni?oii i?iaiaeeoue A. aai
Eaecai c? ni?a?ia?oieeaie ia i?ioyc? inoaii?o 25 ?ie?a, ne?ae ana ae
oaee caoaaaeeoe, ui oiceeiaoee?cii?o?ee ? eeoa iaeiei c aaaaoueio
oe?eaaeo ?aaaaio?a, eio?? iiaeia io?eiaoe ia iniia? i?iaeoeo?a
S-(-ai?aeiaee?ethaaiiy. Oiio aeooaeueiith i?iaeaiith, ia iao iiaeyae, ?
?icaeoie ia iaio aaaeeeaeo ? ?acii c oei a?eueo caaaeueieo iai?yie?a
canoinoaaiiy i?iaeoeo?a S-(-ai?aeiaee?ethaaiiy oa ?o aaciina?aaei?o
iio?aeieo a i?aai?/iiio neioac?.
Ca’ycie ?iaioe c iaoeiaeie ieaiaie oa oaiaie. ?iaioa aeeiioaaeanue a
?aieao ieaiiai? athaeaeaoii? oaiaoeee 1984-1999 ??. eaoaae?e i?aai?/ii?
o?i?? Oe?a?inueeiai aea?aeaaiiai o?i?ei-oaoiieia?/iiai oi?aa?neoaoo oa o
a?aeiia?aeiino? c i?iaeoaie Aea?aeaaiiai oiiaeo ooiaeaiaioaeueieo
aeine?aeaeaiue Oe?a?ie (a?aioe 3.3/66 oa 3.4/26 1994-1998 ??.), a oaeiae
I?aeia?iaeiiai iaoeiaiai oiiaeo Aeae. Ni?ina (a?aio U93000, 1994-1995
??.).
Iaoa oa caaaeaiiy aeine?aeaeaiiy. Iniiaia iaoa oeueiai aeine?aeaeaiiy
iieyaaea a nenoaiaoe/iiio aea/aii? ?ie? S-(-ai?aeiaee?ethaaiiy,
S-(-ai?aeiaeeai?ethaaiiy oa nii??aeiaieo i?ioean?a a aaia?aoe??
ooieoe?iiae?ciaaieo aoeeee?/ieo ? iniaeeai aaoa?ioeeee?/ieo nenoai.
Aaaeeeaeie caaaeaiiyie i?e aeeiiaii? ?iaioe aoee oae?:
?ic?iaea c?o/ieo niinia?a iaea?aeaiiy ?yaeo i?iaeoeo?a
S-(-ai?aeiaee?ethaaiiy c ?aaeoe?eiicaeaoieie oa?oiiaaiiyie:
a yeeo aoii n??ee o ooieoe?iiaeueiiio -cai?nieeo ia? oi?iaeueio
aaeaioi?noue 2,4 /e 6;
ia?aoai?aiiy aeinooiieo i?iaeoeo?a S-(-ai?aeiaee?ethaaiiy a ?io? oeie
aeaeo?io?eueieo aaaio?a, ui i?noyoue ?i?aei?eoei?eaeiee o?aaiaio,
?cioe?aiaoia?oio aai ?io? aaoa?ieoioeaiia?oie a (-iieiaeaii? aei
n??eiai?niiai caeeoeo;
canoinoaaiiy i?iaeoeo?a S-(-ai?aeiaee?ethaaiiy oa ?o aeaeo?io?eueieo
iio?aeieo a neioac? iiaeo oei?a aoeeee?/ieo ? aaoa?ioeeee?/ieo NIN.
Iaoeiaa iiaecia iaea?aeaieo ?acoeueoao?a. Aeeiiaii nenoaiaoe/ia
aeine?aeaeaiiy aca?iiae?? e?eueeio oei?a N-(-oei?aee?eai?ae?a c o?ieaie,
o?iiai?aeaie oa a?ainoeueo?iaoaie iao??th, ui i?eaaei aei ?ic?iaee
aeineoue caaaeueiiai iaoiaeo iaea?aeaiiy ??ciiiai?oieo i?iaeoeo?a SII-
oa SVI-ai?aeiaee?ethaaiiy, i?eaeaoieo aeey iiaeaeueoeo ia?aoai?aiue.
Aia?oa aea/aii aeaa?ae?ioei?oaaiiy ?aaaaio?a oeio R1CCl2CH(SO2Ar)NHCOR,
ui noaei iniiaith aeey noai?aiiy noa?ainaeaeoeaiiai niiniao io?eiaiiy
?yaeo i?iaeoeo?a S-(-ai?aeiaeeai?ethaaiiy c ooieoe?iiaeueieie
cai?nieeaie a (-iieiaeaii? a?i?enoeueoii?eueiiai o?aaiaioa.
Aeyniaii o?i?ci iine?aeiaii? aca?iiae?? iaiane/aieo aceaeoii?a c
aiaeith, oei?ii oa a?ainoeueo?iaoaie iao??th, eio?ee iieeaaeaii a iniiao
c?o/iiai i?aeoiaeo aei ?aa?i- oa noa?ainaeaeoeaiiai neioaco aaaaoueio
A-?ciia??a (-noeueoii?ecai?uaieo aiai?ae?a aac ooieoe?iiaeueieo a?oi a
(-iieiaeaii? aeeai?eueiiai caeeoeo.
Anoaiiaeaii, ui aeinooii? i?iaeoeoe S-(-ai?aeiaeeai?ethaaiiy aeaio
oei?a: ClCH=C(SO2R1)NHCOR oa Cl2C=C(SO2R1)NHCOR – i?eaeaoi? aeey neioaco
?yaeo 4-noeueoii?ecai?uaieo ienacie?a. Oae, i?e iine?aeiai?e ia?iaoe?
ia?oeo ?c aeacaieo ?aaaaio?a ii?oie?iii, nieyiith eeneioith oa
o?ii?eoei?eaeii ooai?ththoueny 4-a?eenoeueoii?eienaciee aac
cai?niee?a a iieiaeaii? 5 e?eueoey, a i?e aca?iiae?? ?aaaaio?a ae?oaiai
oeio c a?ae?inoeueo?aeii iao??th aai ai?iaie io?eiai?
4-noeueoii?ecai?uai? ienaciee, ui i?noyoue a iieiaeaii? 5 ua e
ia?-eaioia?oio /e caeeoee AlkNH aai Alk2N.
Aia?oa aeyaeaii, ui aeaeo?io?euei? iaiane/ai? aaaioe aeaio oei?a:
ye? iaea?aeai? c a?aeiia?aeieo i?iaeoeo?a S-(-ai?aeiaeeai?ethaaiiy,
aaaeeea? aeey neioaco ooieoe?iiaeueiicai?uaieo o?acie?a. Oae, i?e
aca?iiae?? aeacaieo ai?i?aei?eoei?eae?a c a?ae?inoeueo?aeii iao??th
io?eiai? 4-a?eenoeueoii?e-5-ia?eaioio?aciee, a ai?cio?ioe?aiaoe, ui
i?aaenoaaeai? aeua, aeathoue c aenieiiniiaieie ai?iaie iaa?aeii? ?ai?oa
2-aee?eai?ii(ae?aee?eai?ii)-4-a?eenoeueoii?e-5-oei?o?aciee.
Ciaeaeaii, ui i?e iaa??aaii?
N-(1-oai?enoeueoii?e-2,2-aeeoei?aoai?e)iaoeeea?aaiaoo c iaioaoei?eaeii
oinoi?o ooai?th?oueny ia o?eueee a?aeiia?aeiee ai?cioe?aiao, aea e
oe?eaaee ea?aiae??i?aeiee ?aaaaio
eio?ee i?e iine?aeiai?e ae?? a?iiaoe/ieo oa ae?oaoe/ieo ai?i?a
ia?aoai?th?oueny a iia? iio?aei? ?i?aeacieo:
I?e ooai?aii? ia?oeo ?c ieo, e??i aaoa?ioeeee?caoe??, a?aeaoaa?oueny
i?a?aoe?y oai?enoeueoii?eueiiai caeeoeo, ui iaae?eii aeiaaaeaii
?aioaaiino?oeoo?iei aeine?aeaeaiiyi. Iieacaii, ui eiiaeainaoe??
??ciiiai?oieo (-a?eenoeueoii?ecai?uaieo aiai?ae?a oa a?aeiia?aeieo
ai?i?aei?eoei?eae?a c ai?aeeiaie, ye? i?ioiaeyoue oe?eeii ni?yiiaaii ?
noi?iaiaeaeothoueny ae?i?ioaaiiyi a?eenoeueoii?eueieo a?oi, – aaaeeeaee
i?aia?aoeaiee i?aeo?ae aei 2,4,6-o?ecai?uaieo s-o?eacei?a.
C’yniaaii i?e/eie ?aa?inaeaeoeaiiai S-?i?aei?eaee?ethaaiiy i?e
aca?iiae?? N-(1-oei?aaicee)aaic?i?aei?eoei?eaeo oa eiai aiaeia?a c
o?ina/iaeiaie, ui i?eaaei aei iiaeo iio?aeieo
6-ai?ii-2I-1,3,5-o?aae?aceio.
Anoaiiaeaii, ui aeinooii? ?aaaaioe caaaeueii? oi?ioee ArCCl=NCH2SO2Ar1
i?e iine?aeiai?e ia?iaoe? ?iaeai?aeii iao??th, ia?aeiieie aai aoi?eiieie
a?iiaoe/ieie ai?iaie oa a?ae?ieneaeii iao??th aeathoue a?aeiia?aei?
iio?aei? 6-ia?eaioi-1,2-aeea?ae?io?eaceio aai 2I-1,3,5-o?aae?aceio.
Ooai?aiiy inoaii?o a?aeaoaa?oueny ca ?aooiie aioo??oiueiiieaeoey?iiai
S-?i?aei?eiaoeethaaiiy c ae?i?ioaaiiyi a?eenoeueoii?eueii? a?oie.
Oaeei /eiii, a ?acoeueoao? nenoaiaoe/ieo aeine?aeaeaiue
S-(-ai?aeiaee?ethaaiiy oa nii??aeiaieo i?ioean?a a i?aeoeeo oiieiai
i?aai?/iiai neioaco aaeaeiny aaanoe /eiaei iiaeo ?aaaaio?a c
oa?aeoa?ieie oa?oiiaaiiyie:
aea – ??ciiiai?oi? n??eiai?ni? caeeoee, a O= O, S, NAlk, NAr.
An? oe? ?aaaaioe aeyaeeenue i?eaeaoieie aeey neioaco oaeeo
ooieoe?iiaeueieo iio?aeieo ienacieo, o?acieo, ?i?aeacieo,
1,2,4-o?aae?acieo, s-o?eaceio, 1,2-aeea?ae?i-s-o?eaceio,
2I-1,3,5-o?aae?aceio oa ?ioeo aaoa?ioeeee?/ieo nenoai, eio?? aaaeei
io?eiaoe ?iaeoa.
Oni?oia aeei?enoaiiy i?iaeoeo?a S-(-ai?aeiaee?ethaaiiy, ?o aiaeia?a oa
iio?aeieo a ??cieo aniaeoao i?aai?/iiai neioaco aoei a iaiiaeeeaei aac
aeine?aeaeaiiy aeayeeo caaaeueieo i?iaeai noiniaii:
a) ?ie? “(-aoaeoo” a nii??aeiaieo nenoaiao SII-, SIV- oa
SVI-ai?aeiaee?eth-aaiiy;
a) aieeao i?ioio?ii?? ia noa?aio?i?/iee ?acoeueoao ioeeaio?eueiiai
cai?uaiiy a aiai?aeao;
a) caeaaeiino? ?aa?inaeaeoeaiino? ?i?aei?eaee?ethaaiiy aia?aeaioieo
N,S-ioeeaio?e?a a?ae neiao?e/iino? no?oeoo?e ?aaeoaio?a, i?e?iaee
aeaeo?io?eueieo oeaio??a a 2-acai?iiaiia?e o??aae?, ioeeaiooaiino?
a?aeo?aeii? a?oie oa i?eioeeio “neia?ico”.
I?aeoe/ia cia/aiiy iaea?aeaieo ?acoeueoao?a iieyaa? a ?ic?iaoe? c?o/ieo
i?aeoiae?a aei io?eiaiiy oe?eiai ?yaeo i?ea?iaeueieo iie?oeaio?iaeo
N,S-?aaaaio?a, eio?? a?ae?a?athoue aaaeeeao ?ieue a i?aia?aoeaieo
neioacao iiaeo oei?a iio?aeieo acie?a oa acei?a, na?aae yeeo ciaeaeai?
aoaeoeai? ooia?oeeaee, aa?a?oeeaee oa aaeoa?eoeeaee.
Iniaenoee aianie aaoi?a ? aecia/aeueiei ia an?o aoaiao aeine?aeaeaiiy ?
iieyaa? a caaaeuei?e iinoaiiaoe? i?iaeaie oa iaa?oiooaaii? caaaeaiiy, o
aeai?? ia’?eo?a aeine?aeaeaiiy, naiino?ei?e ?ic?iaoe? iaoiae?a
aenia?eiaioo, aiae?c?, ?ioa?i?aoaoe?? oa ocaaaeueiaii?
aenia?eiaioaeueieo aeaieo, io?eiaieo ia eeoa naiino?eii, aea e o
ni?aaaoi?noa? c ?ioeie aeine?aeieeaie.
Ai?iaaoe?y ?acoeueoao?a aeena?oaoe??. Iaoa??aee aeena?oaoe?eii? ?iaioe
aeiiia?aeaeenue ia V Neiiiceoi? c i?aai?/iiai neioaco (Iineaa, 1988 ?.);
2-e oa 3-e eiioa?aioe?yo iieiaeeo o?i?e?a (Aeiiaoeuee, 1990 ? 1991 ??.);
XVI, XVII, XVIII Oe?a?inueeeo eiioa?aioe?yo c i?aai?/ii? o?i??
(Oa?iii?eue, 1992 ?., Oa?e?a, 1995 ?. oa Aei?i?iiao?ianuee, 1998 ?.).
E??i oiai, aiie aoee i?aaenoaaeai? ia XVI I?aeia?iaeiiio neiiiceoi? c
i?aai?/ii? o?i?? n??ee (Ia?caao?a, 1994?.) oa XV I?aeia?iaei?e
eiioa?aioe?? c o?i?? aaoa?ioeeee?/ieo niieoe (Oaeaae, 1995?.).
Ioae?eaoe??. Iaoa??aee aeena?oaoe?eii? ?iaioe aeeeaaeai? o 31 noaoo?
[1-31], 3 aaoi?nueeeo na?aeioeoaao [32-34] oa oacao 21 aeiiia?ae?
[35-55].
Co?oeoo?a ? ianya aeena?oaoe??. Aeena?oaoe?eia neeaaea?oueny c? anooio,
oanoe ?icae?e?a, aeniiae?a ? nieneo e?oa?aoo?e, ui aeeth/a? 284
iaeiaioaaiiy. O ia?oiio ?icae?e? ?icaeyiooi i?yia
S-(-ai?aeiaee?ethaaiiy, a a ianooiiiio – neioace i?iaeoeo?a
S-(-ai?aeiaeeai?ethaaiiy. O?ao?e oa /aoaa?oee ?icae?ee i?e-nay/ai?
?icaeyaeo aaoa?ioeeee?caoe?e (-noeueoii?ecai?uaieo aiai?ae?a oa
i?iaeoeo?a S-?i?aei?eaee?ethaaiiy, a a i’yoiio ?icae?e? ocaaaeueiai?
aeai? i?i i?aeoe/ii ei?eni? aeanoeaino? ??ciiiai?oieo aoeeee?/ieo oa
aaoa?ioeeee?/ieo NIN, io?eiaieo a ?acoeueoao? aea/aiiy
S-(-ai?aeiaee?ethaaiiy oa nii??aeiaieo i?ioean?a.
Eiaeai c oeeo i’yoe ?icae?e?a ii/eia?oueny ei?ioeei iaeyaeii
e?oa?aoo?e, a aeae? iaaiai?ththoueny aeani? aeine?aeaeaiiy. Ia?aoo? a
inoaiiueiio oinoiio ?icae?e? iaaaaeai? aenia?eiaioaeuei? iaoiaeeee
S-(-ai?aeiaee?ethaaiiy oa ??ciiiai?oieo aaoa?ioeeee?caoe?e ia iniia?
iiaeo iie?ooieoe?iiaeueieo n??eiai?nieo ?aaaaio?a.
?iaioa i?noeoue 34 noaie, 89 oaaeeoeue ? 15 ?enoie?a. Iiaiee ianya
?iaioe 352 noi??iee, c yeeo 139 caeiathoue aeiiii?aei? ?acoeueoaoe.
INIIAI? ?ACOEUeOAOE ?IAIOE
1.Neioace iiaeo i?iaeoeo?a S-(-ai?aeiaee?ethaaiiy oa ?o aca?iiae?y c
iaioaoei?eaeii oinoi?o
Aaea aei ii/aoeo aeeiiaiiy oe??? ?iaioe S-(-ai?aeiaee?ethaaiiy
??ciiiai?oieo niieoe n??ee aoei aeia?a aea/aii. Iaeiae i?i ia?aoai?aiiy
oeeo i?iaeoeo?a a aaoa?ioeeee?/i? niieoee aoei a?aeiii aeoaea iaei.
Iinoaaeaoe nia? ca iaoo aeine?aeeoe iiaeeeaino? ?yaeo i?iaeoeo?a
S-(-ai?aeiaee?ethaaiiy a aeecaei? aaoa?i-oeeee?/ieo nenoai, iaiao?aeii
aoei neioacoaaoe oae? i?aaenoaaieee oeeo ?aaaaio?a aai i?iaeoeoe ?o
ianeeaaeieo ia?aoai?aiue, eio?? iiaeia aoei a aeei?enoaoe aeey
oeeee?caoe?e. Oaea ni?yioaaiiy a aeine?aeaeaii? ia?aoai?aiue i?iaeoeo?a
S-(-ai?aeiaee?ethaaiiy i?eaa?ioei oaaao aei o?ueio oei?a oeeo ?aaaaio?a
c oa?aeoa?ieie o?aaiaioaie:
A?eueo?noue i?aaenoaaiee?a oeeo nenoai iaea?aeaii c aenieeie aeoiaeaie
ca aeiiiiiaith aaciina?aaeiueiai ai?aeiaee?ethaaiiy aeinooiieie
?aaaaioaie (1-4) o?ie?a, o?iiai?ae?a oa a?ainoeueo?iao?a iao??th ca
noaiith 1.
Noaia 1
R=H, Alk, Ar, AlkO; R1=H (1,5,9,13), Cl2CH (2,6,10,14), Cl3C
(3,7,11,15), C6H5CO (4,8,12,16); R2=Alk, Ar; R3=H2N, AlkNH, ArNH, Ar2N
oa ?i.
Ia a?aei?io a?ae ai?aeiaee?ethaaiiy aaaaoueio ia?eaioai?a oa o?ioaiie?a,
ui i?ioiaeeoue i?e aea?iieaeoey?i?e aca?iiae?? ?aaaaio?a, iiae?aia
?aaeoe?y c n??eiaiaeiai a?aeaoaa?oueny, ye i?aaeei, i?e iieueiiio
a?aeiioaii? 2:1.
R1=Cl3C (3,17), C6H5CO (4,18).
Oaeei /eiii, ca aeiiiiiaith aaciina?aaeiueiai S-(-ai?aeiaee?ethaaiiy
aaea?oueny io?eiaoe ??ciiiai?oi? ?aaaaioe (5-18), a yeeo aoii n??ee ia?
oi?iaeueio aaeaioi?noue 2, 3 /e 6. Aeey iaea?aeaiiy i?iaeoeo?a
SIV-(-ai?aeiaee?ethaaiiy iaie canoiniaaii oaea ieeniaiiy:
R=H, C6H5; R1=H (5,19), Cl2CH (6,20), Cl3C (7,21), C6H5C(O) (8,22);
R2=Alk, Ar;
Acyl=CH3C(O), 2-HOC(O)C6H4C(O), 3-ClC6H4C(O).
Iiaeaeueoa ieeniaiiy noeueoieneae?a (19-22) ia? nain eeoa a oiio
aeiaaeeo, eiee a?aeiia?aei? noeueoiie aaaeei aai iaiiaeeeai io?eiaoe ca
noaiith 1.
I?e ae?? iaioaoei?eaeo oinoi?o ia i?iaeoeoe SII- oa
SIV-ai?aeiaee?ethaaiiy /anoi a?aeaoaa?oueny ?icuaieaiiy ca’yceo C-S.
Iaeiae i?iaeoeoe SVI-ai?aeiaee?ethaaiiy aca?iiae?thoue c iaioaoei?eaeii
oinoi?o aac oaeiai ?icuaieaiiy (aeea. noaio 2).
Noaia 2
R=H, Alk, Ar; R1=H (13,23), Cl2CH (14,24,27), Cl3C (15,25,26,28);
R2=Alk, Ar.
Oi/a ia?aoai?aiiy, i?aaenoaaeai? ia noai? 2, ? aeineoue o?ea?aeueieie,
iaeiae a?ae oeueiai ?o ei?enoue ia ciaioo?oueny, ai an? aiie ?
i?aia?aoeaieie ? aei oiai ae ?aaaaioe (23-28) aeyaeeenue aaaeeeaeie aeey
aaaaoueio aaoa?ioeeee?caoe?e c ioeeaio?eaie (aeea. ?icae. 3). ?ieiee
aaoa?ioeeee?caoe?? a?aeaoaathoueny aaea i?e ia?iaoe? iaioaoei?eaeii
oinoi?o aeayeeo ooieoe?iiae?ciaaieo i?iaeoeo?a S-(-ai?aeiae-e?ethaaiiy:
= ArS (8, 29), ArSO2 (16,30).
Ia?aoai?aiiy: 8_29, 16_30 oa 18_31 – /anoeia? aeiaaeee eeane/iiai
neioaco ienacie?a ca ?ia?inii-Aaa??aeai. Noa?o ?o canoinoaaiiy,
i/aaeaeii, aaeanoueny ?icoe?eoe, ai aeey neioaco aiaeia?a ?aaaaio?a
(8,16,18) iiaeia aeei?enoaoe ia o?eueee a?eeae?ienae?, aea e ?io?
(-aeeea?aii?euei? niieoee.
2. Iaea?aeaiiy i?iaeoeo?a S-(-ai?aeiaeeai?ethaaiiy
oa ?o ?aaeoe?eiicaeaoieo iio?aeieo
I?yia S-(-ai?aeiaeeai?ethaaiiy canoiniao?oueny aeoaea ??aeei ? aeey
iaea?aeaiiy n??eiai?nieo aiai?ae?a aoee ?ic?iaeai? ?io? i?aeoiaee.
Iaeaaaeeea?oee ?c ieo iia’ycaiee c aeaa?ae?ioei?oaaiiyi ?aaaaio?a
(14,15).
Aeyaeeinue, ui aeaa?ae?ioei?oaaiiy ?aaaaio?a (14, R1=H) ca aeiiiiiaith
o?eaoeeai?io – noa?ainaeaeoeaiee i?ioean, yeee i?eaiaeeoue aei
A-?ciia??a (-noeueoii?ecai?uaieo aiai?ae?a (32, R1=H), eio?? a naith
/a?ao aeei?enoai? aeey neioaco A-?ciia??a ?ioeo
(-ooieoe?iiaeueiicai?uaieo n??eiai?nieo aiai?ae?a (34). Aeey iaae?eii?
?aeaioeo?eaoe?? i?inoi?iai? aoaeiae oeeo i?iaeoeo?a, e??i eiiieaeniiai
niaeo?aeueiiai aeine?aeaeaiiy, no?oeoo?e aeaio ?c ieo aoee aea/ai? ca
aeiiiiiaith ?aioaaiino?oeoo?iiai iaoiaeo. Ia ?en.1 aeaeii, ui a
i?iaeoeo? aeaa?ae?ioei?oaaiiy
N-(1-oicee-2,2-aeeoei?aoee)o?eiaoeeaoeaoai?aeo ia? i?noea
oeen-i???ioaoe?y a?aeiinii ca’yceo N=N aoiia aiaeith oa oiceeueii?
a?oie. Oe?eaai, ui i?e cai?uaii? a iueiio ?ooeeaiai aoiia oei?o a?ey
ca’yceo N=N ia caeeoie ii?oie?io i?inoi?iaa aoaeiaa ia ci?ith?oueny, ai
ooai?th?oueny aieiaiei /eiii A-?ciia?
N-(2-ii?oie?ii-1-oiceeaoai?e)o?eiaoeeaoeaoai?aeo (aeea. ?en.2).
Ia ia?oee iiaeyae caea?oueny, ui anoaiiaeaiiy noa?aio?i?/iiai
?acoeueoaoo iaio noaae?e ia?aoai?aiiy 14_32_34 aea? iiaeeea?noue
?icaeyiooe a?eueo aeaoaeueii eiai iaoai?ci. Iaeiae o?aaa iaoe ia oaac?,
ui aaea ca cae/aeieo oiia iiaea a?aeaoaaoeny Z_E-?ciia?ecaoe?y aiai?ae?a
aiane?aeie i?ioio?ii??:
I?eeiath/e aei oaaae oeth ianoaaeio, iaa?yae /e iiaeia a aeaiiio
aeiaaeeo iaeiicia/ii anoaiiaeoe noa?aio?i?/i? iniaeeaino? ie?aieo
noaae?e aeaa?ae?ioei?oaaiiy ? ioeeaio?eueiiai cai?uaiiy a?ey ca’yceo
C=C. Iaa?oue oiae?, eiee iaeaea? oe? noaae?? ia ? noa?ainaeaeoeaieie, oi
a ?acoeueoao? ?ciia?ecaoe?? aaea ca cae/aeieo oiia oa?iiaeeiai?/ii iaio
aea?aeieo aiai?ae?a, e?ioeaaee ?acoeueoao ia?aoai?aiiy aoaea aeacoaaoe
ia aenieo noa?ainaeaeoeai?noue i?ioeano a oe?eiio. Caoaaaeeii, ui
ooai?aiiy A-?ciia??a (-noeueoii?ecai?uaieo aiai?ae?a ni?ey?
i?iaaaeaiith aaoa?ioeeee?caoe?e ca o/anoth i?inoi?iai iaaeeaeaiiai
aoiia oei?o aai ?ioiai ooieoe?iiaeueiiai cai?n-
?en.1. Iieaeoey?ia no?oeoo?a A-?ciia?o
N-(1-oicee-2-oei?aoai?e)o?eiaoee-aoeaoai?aeo (32a) ca ?NAe.
?en.2. Iieaeoey?ia no?oeoo?a A-?ciia?o
N-(2-ii?oie?ii-1-oiceeaoai?e)o?e-iaoeeaoeaoai?aeo (34a) ca ?NAe.
ieea aei aoeeeai?iii? a?oie (aeea. ?icae?e 3.).
Aeey io?eiaiiy (-noeueoii?ecai?uaieo aiai?ae?a, ui ia i?noyoue
ooieoe?iiaeueieo oa?oiiaaiue a (-iieiaeaii? aeeai?eueiiai caeeoeo, iaie
?ic?iaeaii e?eueea i?aeoiae?a, eio?? i?aaenoaaeai? ia noai? 3.
Iaeaaaeeea?oee c ieo – iine?aeiaia ia?iaea aeinooiieo (,(-iaiane/aieo
(-aoeeeai?iiea?aiiiaeo eeneio (35,36) oei?ii ? a?ainoeueo?iaoaie
iao??th. Iacaaaeath/e ia i’ye? oiiae eiiaeainaoe??, a?aeaoaa?oueny ia
o?eueee cai?uaiiy ia a?eenoeueoii?eueio a?oio ?ooeeaiai aoiia oei?o a
i?ii?aeieo niieoeao (37,38), aea e iiaeaeueoa aeaea?aieneethaaiiy oa
ooai?aiiy ca’yceo N=N, ui i?eaiaeeoue aei ooai?aiiy iaa?aeiieo ?ai?oa
(-a?eenoeueoii?ecai?uaieo aiai?ae?a (43,44) c aeoiaeaie 50-60%. Ne?ae
cacia/eoe, ui iaiao?aei? aeey oeueiai neioaco iaiane/ai? eeneioe (35,36)
iiaeia io?eiaoe eiiaeainaoe??th i??iaeiia?aaeii? eeneioe c
a?aeiia?aeieie ai?aeaie /e ?icuaieaiiyi iaiane/aieo aceaeoii?a. Oe?eaai,
ui Z-?ciia?e iaiane/aieo aceaeoii?a, eio?? io?eiai? ca iaoiaeii
Ieaoey-A?eaiiaea?a i?ney iine?aeiaii? ae?? aiaee, oei?o oa
a?ainoeueo?iao?a iao??th ia?aoai?ththoueny a A-?ciia?e
(-noeueoii?ecai?uaieo aiai?ae?a (44). Aoaeiao iaeiiai c ieo (44a,
R=R2=C6H5, R1=H, Ar=4-CH3C6H4) aaeaeiny aeiaanoe ia?aoai?aiiyi o
nii??aeiaiee aiai?aeei (45a), no?oeoo?a yeiai anoaiiaeaia
?aioaaiino?oeoo?iei iaoiaeii (aeea.?en.3).
?en. 3. Iieaeoey?ia no?oeoo?a aiai?aeeio (45a) ca ?NAe.
Caoaaaeeii, ui i?iaeoeoe S-(-ai?aeiaeeai?ethaaiiy, ?icaeyioo? aeua, ca
aeiiiiiaith iaioaoei?eaeo oinoi?o aaeaeiny ia?aoai?eoe a oe?eee ?yae
oe?eaaeo iaiane/aieo n??eiai?nieo niieoe (46-51,53), ui i?noyoue
?aaeoe?eiicaeaoi? oa?oiiaaiiy: –N=CClR, –N=CCl2, –N=C=O, –N=C=S,
–N=C=NBu-t. An? oe? ?aaaaioe iaea?aeai? c aenieeie aeoiaeaie a
?acoeueoao? ianeeaaeieo ia?aoai?aiue, ye? i?aaenoaaeai? ia noai? 4.
Ai?i?aei?eoei?eaee (48,49) io?eiai? ia o?eueee i?e
Noaia 3
R1=R2=H (35, 37, 39, 41, 43); R1=H, R2=Ar (36, 38, 40, 42, 44).
Noaia 4
iaa??aaii? a?aeiia?aeieo aiai?ae?a c iaioaoei?eaeii oinoi?o, aea e a
?acoeueoao? aeaa?ae?ioei?oaaiiy: 25_48, 26_49, yea ?ieiee c?o/i?oa a
i?aia?aoeaiiio a?aeiioaii?. E??i oiai, nii??aeiai? aio?aoaie (33) aeaui
ii-??ciiio a?aeiinyoueny aei iaioaoei?eaeo oinoi?o. sseui Alk=N2I5,
oi ia?aoai?aiiy 33_50 i?ioiaeeoue oe?eeii ni?yiiaaii, a
eiee Alk=CH3 ooai?ththoueny aeaa i?iaeoeoe ?aaeoe?? (50, 54):
Aoaeiao oe?eaaeo iie?oeaio?iaeo aeaeo?io?eueieo ?aaaaio?a (50,54), a
oaeiae ?o aiaeia?a (46-49,51,53) i?aeoaa?aeaeaii ca aeiiiiiaith ?*
niaeo??a oa ??ciiiai?oieo aaoa?ioeeee?caoe?e, ui ?icaeyioo? o ianooiiiio
?icae?e?.
3. Oeeeeieiiaeainaoe?? (-noeueoii?ecai?uaieo aiai?ae?a
oa ?o iio?aeieo c ioeeaio?eaie
Oeeee?caoe?? ca o/anoth (-noeueoii?ecai?uaieo aiai?ae?a aei iaoeo ?ia?o
ia aea/aeenue. Iaie aia?oa aoei ciaeaeaii, ui oe? ?aaaaioe i?eaeaoi?
aeey neioaco aaaeeeaeo iio?aeieo ienacieo, o?acieo, ?i?aeacieo oa
s-o?eaceio. Oae, ia noai? 5 i?aaenoaaeai? ia?aoai?aiiy aeinooiieo
?aaaaio?a (32,35) o iia? ooieoe?iiaeueii-cai?uai? ienaciee (58-65).
Iaei?ino?o? c ieo 2-aee?e(a?ee)-4-a?eenoeueoii?e-ienaciee (60) – eaaei
ooai?ththoueny i?e iine?aeiai?e ia?iaoe? ?aaaaio?a (32) ii?oie?iii,
nieyiith eeneioith oa o?ii?eoei?eaeii. Inoaiiy noaae?y oeueiai neioaco
57_60 – /anoeiaee aeiaaeie caaaeueii? oeeee?caoe?? ca
?ia?iniiii-Aaa??aeai, ui eaaei eiio?ieth?oueny ca aeiiiiiaith ?*
niaeo??a, a yeeo cieeathoue nioae aaeaioieo eieeaaiue ca’yce?a N=I oa
N-H.
Ooieoe?iiaeuei? iio?aei? niieoe (60), ui i?noyoue o iieiaeaii? 5
ienacieueiiai e?eueoey aaaeeea? cai?nieee: HS, CH3S, AlkNH, Alk2N,
eaaei iaea?aeothoueny c aeinooiieo ?aaaaio?a (33). Iiae?ai? ia?aoai?aiiy
aiai?ae?a caaaeueii? oi?ioee Nl2C=C(X)NHCOR, aea O=N(I)IAlk, CN,
P(O)(OAlk)2, P+Ph3Cl- oa ?io? aeaeo?iiiaeoeaioi?i? cai?nieee aaea
iienai? a e?oa?aoo??, ui iieaaoeei aeieac aoaeiae ?yaeo
aeeooieoe?iiaeueiicai?uaieo ienacie?a (58,59,63,64) niaeo?aeueieie oa
neioaoe/ieie iaoiaeaie. Caoaaaeeii, ui aeaoaeueia aeine?aeaeaiiy
oaooiia??? i?iaeoeo?a aca?iiae?? aiai?ae?a (33) c a?ae?inoeueo?aeii
iao??th ia i?iaiaeeeinue, ai oe? niieoee iaei?ic/eii? iaa?oue a iiey?ieo
?ic/eiieeao. Oiio i?ye ia iiaeia aeeeth/aoe o?iiii? oi?ie niieoe (58),
aea oea ia aieeaa?, cae/aeii, ia ?o iiaeaeueoa S-iaoeethaaiiy oa
ieeniaiiy eiaeii a eoaeiiio na?aaeiaeu? (aeea. ia?aoai?aiiy 58_63 oa
58_64). Aiai?aee (33) eaaei aca?iiae?thoue ia o?eueee c
a?ae?inoeueo?aeii iao??th, aea e c aenieiiniiaieie ia?aeiieie oa
aoi?eiieie ai?iaie, ui aeei?enoaii a i?aia?aoeaieo neioacao ?yaeo aee-
oa o?eooieoe?iiaeueiicai?uaieo ienacie?a (59,65). Inoaii? c ieo iniaeeai
oe?eaa?, ai i?noyoue
Noaia 5
?aaeoe?eiicaeaoio aeueaeaa?aeio a?oio, ui aeiaaaeaii ia?aoai?aiiyi ?o o
a?aeiia?aei? oai?ea?ae?aciie. Aenieo ?ooeea?noue aoii?a oei?o a
aeeoei?iaoeeuei?e a?oi? a iieiaeaii? 2 niieoe (59) iiaeia iiynieoe ca
aeiiiiiaith i?eioeeio a?i?eia??: ae?aee?eai?iia?oia – neeueiee aeiii?
aeaeo?ii?a – ia?aaea? na?e aieea /a?ac acaae??iiao nenoaio, ui iieaaoo?
a?aeuaieaiiy ai?ii?a oei?o. I?e oeueiio ooai?ththoueny, i/aaeaeii,
i?ii?aei? ?iii??a? nie? (62), ye? eaaei a?ae?ie?cothoueny, ui aea?
iiaeeea?noue aaiaeeoe oi?i?eueio a?oio a iieiaeaiiy 2 ienacieueiiai
e?eueoey.
Ua iaeei iiaee oei o?ecai?uaieo ienacie?a aaeaeiny io?eiaoe c
aeinooiiiai ?aaaaioo (66).
O niaeo?? ssI?1I i?iaeoeo?a oeeeeieiiaeainaoe?? (69) ciaeaeaii
neiaeaoiee neaiae i?e (~ 7.9 i.ae., eio?ee iiaeia a?aeianoe aei neaiaeo
i?ioiia aeeoei?iaoeeueii? a?oie. Aei oiai ae a i?ioean? neeaaeiiai
ia?aoai?aiiy 66__69 a?aeuaieth?oueny iaeia c oiceeueieo a?oi, ui
aeiaaaeaii ia o?eueee niaeo?aeueii, aea e iiaiaeaeo?oueny c aeaieie
aeaiaioiiai aiae?co. Oaea ae?i?ioaaiiy aaaeei iiynieoe, yeui i?eeiyoe
aei oaaae o?eueee i?ii?aeio no?oeoo?o (67). Oe?eeii ?iia??ii, ui a?eueo
aaaeeeao ?ieue a?ae?a?a? oaooiia?ia no?oeoo?a (68), a ye?e oiceeueia
a?oia ciaoiaeeoueny a?ey ca’yceo C=N ? oiio ioeeaiooai?noue ?? cia/ii
ca?eueoo?oueny.
E??i cai?uaieo ienacie?a, ia iniia? iiaeo n??eiai?nieo ?aaaaio?a aoei
io?eiaii e?eueea oei?a ooieoe?iiaeueieo iio?aeieo o?acie?a (aeea. noaio
6). An? aiie i?noyoue aee?e- /e a?eenoeueoii?eueio a?oio a iieiaeaii? 4
o?acieueiiai e?eueoey, a a?eueo?noue ?c ieo aei oiai ae i?e N-5 ia?
iaeei c oaeeo cai?niee?a: Cl, SH, SAlk oa SAr. Caa?iaii oaaao, ia?o ca
ana, ia aaoa?ioeeee?caoe?? ca o/anoth n??eiai?nieo ai?i?aei?eoei?eae?a
(46,48), eio?? o?nii ca’ycai? c a?aeiia?aeieie i?iaeoeoaie
S-(-ai?aeiaeeai?ethaaiiy. Iniaeeaee ?ioa?an i?aaenoaaey? ia?aoai?aiiy
48_71, eio?a i?eaiaeeoue aei iaa?aeiieo ?ai?oa 4-noeueoii?ecai?uaieo
5-ia?eaioiienacie?a, ye? eaaei iaoeeththoueny. Iayai?noue a?oie SCH3 a
oeeo i?iaeoeoao iaoeethaaiiy aeiaaaeaii ca aeiiiiiaith niaeo??a ssI?1I.
Iaia? noii?ao a oiio,
Noaia 6
ui aiaeia?/ii iiaeia aaanoe e ?io? aee?eo?ia?oie, aea aeey io?eiaiiy
aiaeia?/ieo 5-a?eeo?io?acie?a ne?ae nei?enoaoeny ?ioei i?aeoiaeii:
48_72_74. Ni?iae cai?ieoe aoii oei?o a ?aaaaioao (72) ia ai?ii- /e
aee?eai?iia?oio aoee aaconi?oi?. Ua iaio ?ooeeaei ? aoii oei?o a
cai?uaieo o?acieao (77,78), ui iaoiiaeaii aieeaii aeaeo?iiiaeiii?ieo
a?oi, yeee ia?aaea?oueny /a?ac 2-aca-1,3-ae??iiao nenoaio ? ciaioo?
aeaeo?io?euei?noue oeaio?a N-5. Ia a?aei?io a?ae ?aaaaio?a (72) ?o
aeacaeoeaiaai? aiaeiae (77,78) aaea ia aca?iiae?thoue i? c
a?ae?inoeueo?aeii iao??th, i? c o?ioaiieyoaie eoaeieo iaoae?a. C ?ioeo
ia?aoai?aiue, ui i?aaenoaaeai? ia noai? 6, caa?iaii oaaao ia
oeeeeieiiaeainaoe?? 1-a?eenoeueoii?e-2,2-aeeoei?aoai?e?cio?ioe?aiao?a
(51) c ai?aeii, ia?aeiieie oa aoi?eiieie ai?iaie, ye? i?eaiaeyoue aei
o?ecai?uaieo o?acie?a (77,78). Aeoaea ?iia??ii, ui aaaeeeao ?ieue i?e
oeueiio a?ae?a?athoue cai?uai? N-a?i?eo?ina/iaeie (75,76).
Aeaye? i?aaenoaaieee no?oeoo?e (78) aaeaeiny io?eiaoe ia o?eueee ca
aeiiiiiaith i?aeoiaeo 51_76_78, aea e i?e ia?iaoe? aoi?eiieie ai?iaie
?i?aei?eoei?eae?a oeio Cl2C=C(SO2Ar)N=CClNR2, ui neoaeeoue aaaeeeaei
aeieacii ?o aoaeiae. Aeey anoaiiaeaiiy aoaeiae an?o ?ioeo i?iaeoeo?a
oeeee?caoe?? (70-74,77) oe?iei canoiniaoaaeenue niaeo?aeuei? iaoiaee.
Oae, ca aeiiiiiaith ?* niaeo??a eaaei i?ine?aeeoaaoe cieeiaiiy
aoeeee?/iiai 2-aca-1,3-ae??iiaiai o?aaiaioa a ?aaaaioao (46,48) i?e
ia?aoai?aii? ?o a a?iiaoe/i? niieoee (70,72,73,74). ?acii c oei a
niaeo?? ssI?13N i?iaeoeoo aca?iiae??
1-oicee-2,2-aeeoei?aoai?e?cio?i-oe?aiaoo c ii?oie?iii o neaaiio iie?
aaeaeiny iaae?eii ?aeaioeo?eoaaoe o?e ?aciiaini? neaiaee aoii?a
aoaeaoeth o?acieueiiai e?eueoey: 144.9 (N-2), 116.5 (N-4),166.0 (N-5)
i.ae., caaaeyee ii??aiyiith ?o c a?aeiieie iio?aeieie 2-ai?iio?acieo.
Ne?ae cacia/eoe ia?aoo?, ui ia?aoai?aiiy: 46_70, 48_71 aai 72 iiae?ai?
ia oeeee?caoe?? oinoi?iai?nieo ?aaaaio?a c oa?aeoa?iei o?aaiaioii
ye? aoee aea/ai? aei iaoeo aeine?aeaeaiue (aeea. I.I. Eiaaiia, A.I.
Ia?oeithe, A.N. Ae?a/, AEIO, 1980, 50, 2248-2257 ).
?acii c oei ia?aoai?aiiy: 53_75_77, 51_75_77 oa 51_76_78 oe?eeii
i?ea?iaeuei? ? ia canoiniaoaaeenue ?ai?oa aeey aaaaeaiiy ?ioeo
aeaeo?iiiaeoeaioi?ieo a?oi a iieiaeaii? 4 o?acieueiiai e?eueoey. Iaeiae
iacaeaaeii a?ae ??aiy i?ea?iaeueiino? ia?aoai?aiue noaie 6, an? aiie
nooo?ai aeiiiaiththoue o? iaoiaee neioaco ooieoe?iiaeueiicai?uaieo
o?acie?a, ye? aoee ciaeaeai? ?ai?oa. Ia a?aei?io a?ae ?icaeyiooeo aeua
neioac?a, eio?? iaci?iii caaa?oothoueny aaaaeaiiyi aee?e- /e
a?eenoeueoii?eueieo a?oi a o?acieueia e?eueoea, iaie ciaeaeaia
oeeeeieiiaeainaoe?y 1-oicee-2-oei?aoai?eai?ae?a (32) c
N-a?eeo?ina/iaeiaie, ui noi?iaiaeaeo?oueny ae?i?ioaaiiyi
i-oieoienoeueo?iiai? eeneioe (aeea. noaio 7). Aeey anoaiiaeaiiy oiai, ui
a oeeee?caoe?? i?eeia? o/anoue aoii acioo a?eeai?iiiai caeeoeo, a ia
ia?aeiii? ai?iia?oie aeiaaeinue iaeei c i?iaeoeo?a oeeeeieiiaeainaoe??
(81a, R=Ar=C6H5) ia?aoai?eoe o a?aeiia?aeiee ia?oei?ao (82a) ?
aeine?aeeoe eiai aoaeiao ?aioaaiino?oeoo?iei iaoiaeii. C ?en. 4 aeaeii,
ui aoii acioo, ca’ycaiee c oai?eueiei caeeoeii, ae?enii aoiaeeoue o
o?acieueia e?eueoea, ui i?eaiaeeoue aei ooai?aiiy iaa?aeiiiai oeio
/aoaa?oeiieo o?acie??aeo nieae, ye? i?noyoue a iieiaeaii? 2 oa 4
a?aeiia?aeii ai?ii- oa aoeeeai?iia?oie. Noa?a canoinoaaiiy oe??? iiai?
oeeeeieiiaeainaoe?? c ae?i?ioaaiiyi oiceeueii? a?oie caneoaiao? ia
iiaeaeueoa aea/aiiy.
Noaia 7
?en.4. Iieaeoey?ia no?oeoo?a cai?uaii? o?acie??ai? nie? (82a) ca ?NAe
(ai?ii ia iieacaiee).
E??i ia?, iaie ciaeaeaii ua aea? oeeee?caoe??, a yeeo niinoa??aaeinue
a?aeuaieaiiy a?eenoeueoii?eueieo caeeoe?a (aeea. noaie 8,9). Oae, i?e
iine?aeiai?e ia?iaoe? cai?uaiiai aeea?i?eea?aiae??i?aeo (54) nii/aoeo
ia?aeiieie a?iiaoe/ieie ai?iaie, a iio?i o?ao-aooeeai?iii aai ii?oie?iii
ooai?ththoueny iio?aei? ?i?aeacieo (85,86), aoaeiaa yeeo oe?eeii
ocaiaeaeo?oueny c aeaieie ?* oa ssI?1I niaeo??a. Ia?aoai?aiiy 83_84
iiae?aia ia neioace iio?aeieo 5-oei?o?acieo (aeea. noaio 6), a
ioeeaio?eueia cai?uaiiy aoiia oei?o i?e N-5 ia oai?enoeueoii?eueio a?oio
(84_85) iaoiiaeaia, i/aaeaeii, aieeaii oai?enoeueoii?eueii? a?oie a
iieiaeaii? 4 ?i?aeacieueiiai e?eueoey. Oaeei /eiii, a i?ioean?
neeaaeiiai ia?aoai?aiiy 83__85, e??i aaoa?ioeeee?caoe??, a?aeaoaa?oueny
i?a?aoe?y oai?enoeue-oii?eueii? a?oie, ui aeiaaaeaii ?aioaaiino?oeoo?iei
aeine?aeaeaiiyi (aeea. ?en. 5). sseui a ?aaeoe?ei?e noi?o? ? iaaeeeoie
aenieiiniiaiiai ai?io, oi ooai?ththoueny e?ioeaa? i?iaeoeoe
oeeeeieiiaeainaoe?? (86). Ia aeeeth/aii, ui a oeeo ia?aoai?aiiyo
aaaeeeao ?ieue a?ae?a?athoue ia nai? niieoee (83), a ?o i?ioio?iii?
oaooiia?e c oa?aeoa?iei ni?yaeaiei o?aaiaioii
o yeiio iaeia c oai?enoeueoii?eueieo a?oi ciaoiaeeoueny a?ey N=N
ca’yceo, ui iaoiiaeth? ?? aenieo ioeeaiooai?noue.
Aiaeia?/ia oaooiia?ia oi?ia ?, i/aaeaeii, i?ii?aeiith ? i?e aca?iiae??
(-noeueoii?ecai?uaieo aiai?ae?a (32,33,43,44) c ai?aeeiaie, eio?a
i?eaiaeeoue aei 2,4,6-o?ecai?uaieo s-o?eacei?a (88) ? noi?iaiaeaeo?oueny
a?aeuaieaiiyi a?ainoeueo?iiaeo eeneio. Iiae?aia oeeeeieiiaeainaoe?y
oa?aeoa?ia ? aeey n??eiai?nieo ai?i?aei?eoei?eae?a (46-48, aeea. noaio
9).
Noa?a canoinoaaiiy oeeo oeeee?caoe?e aeoaea oe?iea. Ca ?o aeiiiiiaith a
o?eaceiiaa e?eueoea aaiaeyoueny o?e ??cieo cai?nieee. Iaeei ?c ieo –
iaoeeueia aai cai?uaia iaoeeueia a?oia:CH2Ar, CH2Cl, CH2SAr, CH2SO2Ar,
CHCl2. E??i oiai, cai?nieee R- ia o?eueee ??ciiiai?oi? aee?euei? oa
a?eeuei? caeeoee, aea e ae?aee?eai?iia?oie. A ?* niaeo?ao oeeo niieoe
a?aenooi? nioae iiaeeiaiiy a ?ioa?aae? /anoio 1610-1750 oa 3100-3600
ni-1, ui na?ae/eoue i?i o/anoue aoeeeai?iieo caeeoe?a o oeeee?caoe??.
?acii c oei, aeai? niaeo??a ssI?1I ?yaeo i?aaenoaaiee?a no?oeoo?e (88)
na?ae/aoue i?i iayai?noue a ieo iaoeeueii? aai iaoeeaiiai? a?oie, yea
ooai?th?oueny a ?acoeueoao? ia?aiino i?ioiia. E??i oiai, i?iaeoeo
eiiaeainaoe?? N-1-oiceeaoai?eaaicai?aeo c aaicai?aeeiii aeyaeany
?aeaioe/iei c oei c?aceii 2-iaoee-4,6-aeeoai?e-s-o?eaceio, eio?ee
aoa neioaciaaiee iacaeaaeiei niiniaii.
Oaeei /eiii, aoaeiaa i?iaeoeo?a aca?iiae?? ?aaaaio?a
(32,33,43,44,46-48) c ai?aeeiaie ia aeeeeea? noii?ao. Oey eiiaeainaoe?y
– c?o/iee ? aeineoue caaaeueiee i?aeo?ae aei neioaco o?ecai?uaieo
s-o?eacei?a. Iacaaaeath/e ia oa, ui neioaoe/iee aia?ao o?i?? s-o?eaceio
aeia?a ?icaeiaiee, ciaeaeaiee iaie i?aeo?ae ? iaec?o/i?oei aeey
aaaaeaiiy o?ueio ??cieo cai?niee?a a o?eaceiiaa e?eueoea.
Noaia 8
?en.5. Iieaeoey?ia no?oeoo?a cai?uaiiai ?i?aeacieo (85a) ca ?NAe.
Noaia 9
4. S-(-?i?aei?eaee?ethaaiiy a neioacao iio?aeieo
acioenoeo aaoa?ioeeee?a
Ia a?aei?io a?ae oe?eeii ?aa?inaeaeoeaiiai S-(-ai?aeiaee?ethaaiiy,
aca?iiae?th niieoe n??ee c ?i?aei?eaee?ethth/eie aaaioaie, ui iathoue
?aaeoe?eiicaeaoiee o?aaiaio
aaaeei i?iaanoe eeoa ca o/anoth oeaio?a Nsp3, ai ?ioee aeaeo?io?eueiee
oeaio? Nsp2 a acai?iiaiia?e o??aae? i?iyaey? ia iaioo ?aaeoe?eio
caeaoi?noue. Aeey caaacia/aiiy a?eueoi? ni?yiiaaiino? oaeeo
eiiaeainaoe?e iai caeaaaeinue aaaeeeaei caaacia/eoe iaeneiaeueii
iiaeeeao neiao?e/i?noue no?oeoo?e ?aaeoaio?a. Oea ae?nii aeiiiiiaei i?e
aea/aii? aca?iiae?? neiao?e/iicai?uaieo ?i?aei?eaee?ethth/eo aaaio?a
oeio ArCHClN=CClAr (89) c o?ina/iaeiith oa N,N-aeeoai?eo?ina/iaeiith
(aeea. noaio 10). Oe?eaai, ui a caeaaeiino? a?ae oiia i?iaaaeaiiy
?aaeoe?? iiaeia aeinyaoe o/ano? a oeeeeieiiaeainaoe?? aeaio aoii?a acioo
aai aoii?a acioo ? n??ee o?ina/iaeie (aeea. ia?aoai?aiiy 89_90_91 ?
89__92). O ia?oiio aeiaaeeo ?aaaaioe (89) ia?iaeythoue iine?aeiaii
o?ina/iaeiith ? o?eaoeeai?iii, a o ae?oaiio – eiiaeainaoe?th i?iaiaeyoue
a i?enooiino? o?eaoeeai?io. Aoaeiaa ?ciia?ieo i?iaeoeo?a oeeee?caoe??
(91) oa (92) aeia?a ocaiaeaeo?oueny c? niaeo?aeueieie aeaieie. Ia?aae
on?i iaiiaeeeai ?aii?oaaoe iiae?ai?noue ?* oa ssI?1I oa 13N niaeo??a
niieoee (92a, Ar=C6H5, R=H) oa ?? N,N-aeeoai?eueiiai iio?aeiiai (93a,
Ar=H=C6H5), a yeiio iayai?noue 1,3,5-o?aae?aceiiaiai e?eueoey ia
aeeeeea? noii?ao,
Noaia 10
ai ioeeaio?eueiee oeaio? aeeoai?eai?iia?oie a cia/i?e i???
aeacaeoeaiaaiee ? ia iiaea i?eeiaoe o/ano? a oeeee?caoe??.
?ioa?i?aoaoe?y niaeo??a iio?aeieo 1,2-aeea?ae?i-1,3,5-o?eaceio (91)
aeyaeeanue a?eueo neeaaeiith, ine?eueee o oeueiio aeiaaeeo, e??i
o?ieueii? oi?ie (A), iii?oio ?ieue iiaeooue a?ae?a?aaaoe i?ioio?iii?
oi?ie (A, A, A).
Oae, o niaeo?? ssI?13N niieoee (91, Ar=Ar=C6H5) a aeaeoa?ioei?ioi?i?
inoaii?e neaaiiieueiee neaiae ciaeaeaii i?e 157 i.ae., ui yaii ia
a?aeiia?aea? (C=S ? na?ae/eoue i?i a?aenooi?noue cia/ii? e?eueeino?
oaooiia?o (A). ?acii c oei a ?* niaeo?? ?acaaaeaiiai ?ic/eio oe???
niieoee a aeeoei?iaoai? ?acii c iaei?ioaineaiith nioaith (SH 2535 ci-1,
a ?ioa?aae? /anoio 3350-3550 ci-1 niinoa??aaeenue aea? nioae, ye? yaii
a?aeiinyoueny aei aaeaioieo eieeaaiue aeaio aeineoue ??cieo ca’yce?a
N-H. ?ioaineai?noue iaea?eueo aeniei/anoioii? c ieo nooo?ai caeaaeeoue
a?ae ?icaaaeaiiy ?ic/eio ? ia aeeeth/aii, ui aiia a?aeiia?aea? (NH
iaeiiai c aaoa?iiaeo oaooiia??a (A) aai (A). ?ciia?i? i?iaeoeoe
oeeee?caoe?? (91) oa (92) a?ae??ciythoueny ia o?eueee niaeo?aeueii, aea
e iathoue ??ci? o?i?/i? aeanoeaino?, ui aeaeii c ?o a?aeiioaiiy aei
N-1,2,2,2-oao?aoei?aoee?cioe?aiaoo oa aoeeethth/eo aaaio?a (aeea. noaio
10). I?e/eie, ui iaoiiaeththoue aioo??oiueiiieaeoey?ia
S-?i?aei?eaee?ethaaiiy oeio 89_92 inoaoi/ii ia aeyniai?, aea i?aeaeuaiiy
eiieo?aioii? caeaoiino? S-oeaio?a a i?enooiino? iniiae oe?eeii
c?icoi?ea, a aca?iiae?y “i’yeiai” S-oeaio?a aieiaiei /eiii c ia aeoaea
“aei?noeei” Nsp3-oeaio?ii ?aaaaio?a (89) ocaiaeaeo?oueny c i?eioeeiii
I??niia.
*eneaii? ni?iae ciaeoe oiiae aeey ni?yiiaaieo eiiaeainaoe?e aiaeia?a
?aaaaio?a (89) – aeinooiieo ?i?aei?eoei?eae?a oeio CCl3CHClN=CClAr – c
o?ina/iaeiith, ?iaeai?aeii iao??th oa ?ioeie N,S-ioeeaio?eaie aoee
ia?ieie, ai ia aeeeth/aii, ui Nsp2- oa Nsp3-oeaio?e a oeeo aaaioao
iathoue aeecueeo ?aaeoe?eio caeaoi?noue ? i?iyaeythoue neaaeo
naeaeoeai?noue ii a?aeiioaiith aei N,S oeaio??a. Oiio caeaaaeinue
aeioe?eueiei ciaioeoe ?aaeoe?eio caeaoi?noue ?i?aei?eoei-?eaeiiai
o?aaiaioa ia?aoai?eaoe eiai a ?i?aeaoiee. Oea ia?aaeaa/aiiy aeyaeeinue
ieiaeioai?iei, ai ?aaaaioe (96) aeyaeeenue a?eueo i?eaeaoieie aeey
?aa?inaeaeoeaieo eiiaeainaoe?e c N,S-ioeeaio?eaie, /ei ?o
?i?aei?eoei?eaei? aiaeiae. Oae, ?aaaaioe (96) oe?eeii ni?yiiaaii
aca?iiae?thoue c ?iaeai?aeii iao??th, aea cai?noue i/?eoaaieo
i?iaeoeo?a S-?i?aei?eaee?ethaaiiy (97) io?eiothoueny iaa?aeii?
?ai?oa ?aaaaioe (98), eio?? aeae?eai? a ?iaeea?aeoaeueiiio noai? (aeea.
noaio 11).
Noaia 11
Aiie eaaei i?e?aeiothoue ai?ae oa ai?ie, aea o?ina/iaeie (99)
o?eueee c??aeea aaeaeiny aeei?enoaoe aeey aioo??oiueiiieaeoey?ii?
oeeee?caoe?? 99_100. O niaeo?? ssI?13N niieoee (100a, Ar=4-CH3C6H4)
ciaeaeaii neaiae o aeoaea neaaiio iie? (( 176.33 i.ae.),yeee c aaeeeith
aeieath ?iia??iino? iiaeia a?aeianoe aei aoiia aoaeaoeth ca’yceo C=S.
I?ney iaoeethaaiiy oeae neaiae uaca?, ine?eueee ia?aoai?aiiy 100_101
i?ioiaeeoue c o/anoth ca’yceo C=S.
Ua iaeiei iai?yieii noai?aiiy ?aa?inaeaeoeaieo ?i?aei?eaee?ethth/eo
aaaio?a ? /anoeiaa aai iiaia aeacaeoeaaoe?y oeaio?a Nsp3 a acai?iiaiia?e
o??aae?. O oeueiio a?aeiioaii? oe?eaai ii??aiyoe ?aaeoe?eio caeaoi?noue
aeaio oei?a aeaeo?io?eueieo aaaio?a:
Ia?o? c ieo neeaaeii ?aaaothoue c o?ina/iaeiith,
N,N’-aeeiaoeeo?ina/iaeiith oa ?iaeai?aeaie eoaeieo iaoae?a, a ae?oa?
cia/ii naeaeoeai?oa aca?iiae?thoue c N,S-ioeeaio?eaie, ai ?o
iaoeethth/ee oeaio? i?iyaey? cia/ii iaioo aeoeai?noue ii??aiyii c
?i?aei?eueiei (aeea. noaio 12). Oae, ?aaaaioe (23) eaaei ? oe?eeii
?aa?inaeaeoeaii aca?iiae?thoue c ?iaeai?aeii iao??th ? aeathoue
i/?eoaai? ?i?aei?e?cio?ioe?aiaoe (102), eio?? aeei?enoai? aeey io?eiaiiy
iiaeo iio?aeieo 1,2-aeea?ae?i-1,3,5-o?eaceio (108) oa
2I-1,3,5-o?aae?aceio (109). Nii/aoeo ?aaaaioe (102) ia?iaeyeenue
ia?aeiieie a?iiaoe/ieie ai?iaie /e aeeoai?eai?iii, ui i?eaiaeeei aei
aoeeee?/ieo i?iaeoeo?a i?e?aeiaiiy (103,106), ye? iio?i oeeee?coaaeenue
i?e ae?? a?ae?ieneaeo aai iaoeeaoo iao??th. Oe? aioo??oiueiiieaeo-ey?i?
oeeeeieiiaeainaoe?? i?ioiaeyoue oe?eeii ?aa?inaeaeoeaii ca o/anoth N-
aai S-ioeeaio?eueiiai oeaio?a o?io?a?aeiiai o?aaiaioa ? aeaeo?io?eueiiai
oeaio?a iaoeeaiiai? a?oie, ui i?eaiaeeoue aei ae?i?ioaaiiy
a?aeiia?aeiiai a?ainoeueo?iaoai?iio. Oe?eaai, ui ?c aeaio iiaeeeaeo
eiiaeainaoe?e: 103_107 ? 103_108 iani?aaae? i?ioiaeeoue eeoa inoaiiy.
Aeey c’ynoaaiiy i?e/eie ?aa?inaeaeoeaiino? ei?enii ?icaeyiooe aeaa
ia?ao?aei? noaie :
sseui i?eeiyoe aei oaaae i?eioeei “neia?ico”, oi ae?oaee ia?ao?aeiee
noai iiaeiai aooe a?eueo noaa?e?ciaaiee ca ?aooiie oiai, ui a?ey
N-aeaeo?io?eueiiai oeaio?o eii?aeeio?oueny a?eenoeueoii?eueia a?oia oa
aoii acioo, ye? aeecuee? ca nai?th “aei?noe?noth”. Oiio a?aeaoaa?oueny
oeeee?caoe?y 103_108. Ioeeaio?eueiee oeaio? ia oa?i?iaeueiiio aoii?
acioo a ?aaaaioao (106) iano?eueee aeacaeoeaiaaiee aeaiia oai?eueieie
?aaeeeaeaie, ui ia iiaea eiieo?oaaoe c S-oeaio?ii o?io?a?aeiiai caeeoeo.
Aiane?aeie oeueiai noa? iiaeeeaei aioo??oiueiiieaeoey?ia
S-?i?aei?e-iaoeethaaiiy 106_109.
Aoaeiaa i?iaeoeo?a N-?i?aei?eiaoeethaaiiy (108) oa
S-?i?aei?eiaoeethaaiiy (109) aeia?a ocaiaeaeo?oueny ?c niaeo?aeueieie
aeaieie. Oae, o niaeo?? ssI?1I nii??aeiaieo ia? niieoe (108) oa (109)
o?icnoae i?ioii?a iaoeeaiiai? a?oie a?ae??ciythoueny a?eueoa /ei ia 0.5
i.ae., ui iaoiiaeaii iayai?noth a aaoa?ioeeeeao ??cieo o?aaiaio?a:
NCH2N oa NCH2S. E??i oiai, ca’ycie C=S a niieoeao
Noaia 12
R=C6H5, 4-CH3C6H4, 4-CH3OC6H4; Ar=C6H5, 4-CH3C6H4;
Ar’=C6H5, 4-CH3C6H4, 4-CH3OC6H4, 4-BrC6H4 oa ?i.; X=Cl (104), Ar1NH
(105).
(108a,R=4-CH3C6H4, Ar=C6H4) ? (106a, R=C6H5, Ar=4-CH3C6H4) aaeaeiny
?aeaioeo?eoaaoe ca aeiiiiiaith niaeo??a ssI?13N, ui i?noyoue neaiaee o
neaaiio iie? a ?ioa?aae? ( 176-180 i.ae. Iio?aei?
6-ia?eaioi-1,2-aeea?ae?i-1,3,5-o?eaceio (108), oi/a ? ciaoiaeyoueny
aieiaiei /eiii o o?iii?e oi?i?, ana ae oaee eaaei ieeniththoueny eiaeii
aei a?aeiia?aeieo aeenoeueo?ae?a. ?acii c oei iio?aei?
2I-1,3,5-o?aae?aceio (109) c eiaeii ia ?aaaothoue. Caoaaaeeii, ui
ia?aoai?aiiy 106_109, nooo?ai aeiiiaith? o? i?aeoiaee, ye?
aeei?enoiaoaaeenue ?ai?oa aeey io?eiaiiy iaaaeeei? e?eueeino? iio?aeieo
2I-1,3,5-o?aae?aceio.
Iiaeeea?noue canoinoaaiiy a o?i?? aaoa?ioeeee?a ia?niaeoeaieo ?aaaaio?a
– N-a?eenoeueoii?eiaoee?i?aei?e?cio?ioe?aiao?a (102) – cian?i ia
ae/a?io?oueny eeoa oeie neioacaie, ui ?icaeyioo? aeua. Ia ?o iniia?
aaeaeiny io?eiaoe ua aeaa oeie ia?niaeoeaieo ?aaaaio?a (104,105), eio??
ooai?ththoueny i?e ia?iaoe? niieoe (102) oa (103) oei?ii. Oe?
oeeee?caoe?? ? /anoeiaei aeiaaeeii ooai?aiiy o?aae?acie??aeo nieae ia
iniia? ?i?aei?e?cio?ioe?aiao?a oa a?aeiia?aeieo o?ina/iaei. Oae?
oeeee?caoe?? i?ioiaeyoue iano?eueee eaaei, ui caaaaeathoue ?ieiee
S-(-?i?aei?eaee?ethaaiith. Oae, i?e ae?? oei?o ia ?aaaaioe (110)
i/?eoaaia S-(-ai?aei-aee?ethaaiiy, yea iiaeiii aoei a i?eaanoe aei
niieoe (113), ia a?aeaoaa?oueny, ai oaeaeei ooai?ththoueny cai?uai?
1,2,4-o?aae?acie??a? nie? (114).
Aea?? i?ae no?oeoo?aie (113) oa (114) aaeaeiny c?iaeoe o?eueee i?ney
?aoaeueiiai aiae?co aeaieo ?*, ssI?13N oa ssE?35Nl niaeo??a. Oae, a
niaeo?? ssE?35Nl i?iaeoeoo oei?oaaiiy
N-2,2-aeeoei?aoai?eaaic?i?aei?e?cio?ioe?aiaoo ciaeaeaii eeoa o?e neaiaee
a ?ioa?aae? /anoio 38.7-37.6 IAoe, ui aeicaiey? aeeeth/eoe no?oeoo?o
(113), aeey yei? ne?ae aoei /aeaoe iiyae /ioe?ueio neaiae?a. ?acii c
oei, ca aeiiiiiaith niaeo??a ssI?13N aaeaeiny ?aeaioeo?eoaaoe
aeeoei?a?i?eueio a?oio a ?aaaaioao (110) ? i?iaeoeoao ?o oeeee?caoe??
(114).
Oaeei /eiii, oei?oaaiiy ?i?aei?e?cio?ioe?aiao?a (110), oi/a ? ia
i?eaaei aei ciaoiaeaeaiiy ua iaeiiai oeio S-?i?aei?eaee?ethaaiiy, aea
aoei ei?eniei, ai aeaei ciiao a?aee?eoe c?o/iee i?aeo?ae aei neioaco
iaa?aeiieo ?ai?oa 2,3-aeecai?uaieo 5-oei?-1,2,4-o?aae?acie??aeo nieae,
eio?? i?iyaeythoue aenieo ?aaeoe?eio caeaoi?noue ? caneoaiaothoue
iiaeaeueoiai aea/aiiy.
AENIIAEE
Nenoaiaoe/ia aeine?aeaeaiiy aca?iiae?? N-(-oei?aee?eai?ae?a c o?ieaie,
o?iiai?aeaie oa a?ainoeueo?iaoaie iao??th iieacaei, ui oeae i?aeo?ae ?
c?o/iei ? aeineoue caaaeueiei niiniaii neioaco aaaaoueio i?iaeoeo?a SII-
oa SVI-(-ai?aeiaee?ethaaiiy.
Ciaeaeaii, ui aeey io?eiaiiy i?iaeoeo?a SIV-(-ai?aeiaee?ethaaiiy aa?oi
nei?enoaoeny ieeniaiiyi ia?eeneioaie a?aeiia?aeieo (-aoeeeai?iicai?uaieo
noeueo?ae?a.
Iieacaii, ui ?yae i?iaeoeo?a SV?-(-ai?aeiaeeai?ethaaiiy c?o/ii
iaea?aeoaaoe ca noaiith:
aea O – caeeoee ??ciiiai?oieo N- oa S-ioeeaio?e?a. Iaeaea? noaae??
oeueiai i?ioeano /anoi ? noa?ainaeaeoeaieie ? i?eaiaeyoue a iniiaiiio
aei A-?ciia??a (-noeueoii?ecai?uaieo aiai?ae?a, ui aeiaaaeaii ca
aeiiiiiaith o?i?/ieo oa ?aioaaiino?oeoo?ieo aeine?aeaeaiue.
C’yniaaii, ui iine?aeiaia ia?iaea iaiane/aieo aceaeoii?a aiaeith, oei?ii
oa a?ainoeueo?iaoaie iao??th – i?aia?aoeaiee neioac aaaaoueio i?iaeoeo?a
SV?-(-ai?aeiaeeai?ethaaiiy, ye? ia i?noyoue ooieoe?iiaeueieo a?oi
a (-iieiaeaii? aeeai?eueiiai o?aaiaioa. Noa?aio?i?/ia iniaeea?noue
oeueiai aaaaoinoaae?eiiai i?ioeano iieyaa? a oiio, ui Z-?ciia?e
iaiane/aieo aceaeoii?a ia?aoai?ththoueny aieiaiei /eiii a A-?ciia?e
(-noeueoii?ecai?uaieo aiai?ae?a.
Anoaiiaeaii, ui n??eiai?ni? aiai?aee aeaio oei?a:
i?eaeaoi? aeey neioaco iiaeo iio?aeieo ienacieo. Oae, ia?o? c ieo
aeei?enoai? aeey io?eiaiiy 2-R-4-a?eenoeueoii?eienacie?a aac cai?niee?a
o iieiaeaii? 5 aaoa?ioeeee?/iiai e?eueoey, a ae?oa? aeyaeeenue
iacai?iieie aeey iaea?aeaiiy aee- ? o?eooieoe?iiaeueiicai?uaieo
ienacie?a, eio?? i?noyoue a?ey N-4 aee?e- aai a?eenoeueoii?euei?
caeeoee, a a?ey N-5 e?eueoey ia iaio aaaeeea? ooieoe?iiaeuei? a?oie: SH,
SAlk, NHAlk, NAlk2. A iieiaeaiiy 2 oeeo ienacie?a, e??i aee?eueieo aai
a?eeueieo cai?niee?a, aaeaeiny aaanoe oae? oa?oiiaaiiy: NI=I, CH=N-NHAr,
C(O)NAlk2 oa N=C(NAlk2)CHCl2.
Aeyaeaii, ui iie?oeaio?ia? aeaeo?io?euei? aaaioe caaaeueieo oi?ioe:
ye? iaea?aeai? c a?aeiia?aeieo i?iaeoeo?a S-(-ai?aeiaeeai?ethaaiiy,
aaaeeea? aeey neioaco iiaeo oei?a ooieoe?iiaeueiicai?uaieo o?acie?a.
Oae, aca?iiae??th ai?i?aei?eoei?eae?a c a?ae?inoeueo?aeii iao??th
io?eiai? 4-a?eenoeueoii?e-5-ia?eaioio?aciee, a iaaaaeai? aeua
ai?cio?ioe?aiaoe aeathoue c ai?iaie iaa?aeii? ?ai?oa 2-aee?eai?ii (aai
ae?aee?eai?ii)-4-a?eenoeueoii?e-5-oei?o?aciee.
Ciaeaeaii, ui i?e iaa??aaii?
N-(1-oai?enoeueoii?e-2,2-aeeoei?aoai?e)-iaoeeea?aaiaoo c iaioaoei?eaeii
oinoi?o ooai?th?oueny ia o?eueee a?aeiia?aeiee ai?cioe?aiao, aea e iiaee
ea?aiae??i?aeiee ?aaaaio
eio?ee i?e iine?aeiai?e ae?? a?iiaoe/ieo oa ae?oaoe/ieo ai?i?a
ia?aoai?th?oueny a oae? iio?aei? ?i?aeacieo:
A i?ioean? ooai?aiiy ia?oeo ?c ieo, e??i aaoa?ioeeee?caoe??, i?ioiaeeoue
i?a?aoe?y oai?enoeueoii?eueiiai caeeoeo, ui aeiaaaeaii
?aioaaiino?oeoo?iei aeine?aeaeaiiyi.
Iieacaii, ui ??ciiiai?oi? (-a?eenoeueoii?ecai?uai? aiai?aee oa
a?aeiia?aei? ai?i?aei?eoei?eaee eaaei eiiaeainothoueny c ai?aeeiaie c
ae?i?ioaaiiyi a?eenoeueoii?eueii? a?oie ? ooai?aiiyi iiaeo
2,4,6-o?ecai?uaieo s-o?eacei?a, eio?? aaaeei io?eiaoe ?ioeie niiniaaie.
Ciaeaeaii oiiae aeey ?aa?inaeaeoeaiiai S-(-?i?aei?eaee?ethaaiiy i?e
aca?iiae?? N-(1-oei?aaicee)aaic?i?aei?eoei?eaeo oa eiai aiaeia?a c
o?ina/iae-iith ? N,N-aeeoai?eo?ina/iaeiith, ui i?eaaei aei iiaeo
iio?aeieo 6-ai?ii-2I-1,3,5-o?aae?aceio.
Aeiaaaeaii, ui i?e oei?oaaii? 1-?cio?ioe?aiaoi-2-aca-1,3-ae??i?a
i/?eoaaia S-?i?aei?eaee?ethaaiiy ia a?aeaoaa?oueny, a ooai?ththoueny
i?iaeoeoe oeeee?caoe?? aac o/ano? ca’yceo N=N. Oaea oeeee?caoe?y
aeyaeeanue caaaeueiith aeey an?o oei?a ?i?aei?e?cio?ioe?aiao?a, ye? i?e
ae?? oei?o eaaei ia?aoai?ththoueny a ?aaeoe?eiicaeaoi?
2-aee?e(a?ee)-5-oei?-1,2,4-o?aae?acie?e oei?eaee.
Anoaiiaeaii, ui aeinooii? ?aaaaioe caaaeueii? oi?ioee ArCCl=NCH2SO2Ar1
i?e iine?aeiai?e ia?iaoe? ?iaeai?aeii iao??th, a?iiaoe/ieie ai?iaie oa
a?ae?ieneaeii iao??th aeathoue iio?aei? 6-ia?eaioi-1,2-aeea?ae?io?eaceio
aai 2I-1,3,5-o?aaeeaceio. Ooai?aiiy inoaii?o a?aeaoaa?oueny aiane?aeie
aioo??oiueiiieaeoey?iiai S-?i?aei?eiaoeethaaiiy c ae?i?ioaaiiyi
a?eenoeueoii?eueii? a?oie.
A ?acoeueoao? ooiaeaiaioaeueieo aeine?aeaeaiue S-(-ai?aeiaee?ethaaiiy,
S-(-ai?aeiaeeai?ethaaiiy oa nii??aeiaieo i?ioean?a a i?aeoeeo oiieiai
i?aai?/iiai neioaco aaeaeiny aaanoe /eiaei iiaeo ?aaaaio?a c
oa?aeoa?ieie oa?oiiaaiiyie:
aea – ??ciiiai?oi? n??eiai?ni? caeeoee, a O= O, S, NAlk, NAr.
An? oe? ?aaaaioe aeyaeeenue i?eaeaoieie aeey neioac?a oaeeo
ooieoe?iiaeueieo iio?aeieo ienacieo, o?acieo, ?i?aeacieo,
1,2,4-o?aae?acieo, 1,3,5-o?eaceio, 1,2-aeea?ae?i-s-o?eaceio,
2I-1,3,5-o?aae?aceio, eio?? o a?eueoino? aeiaaee?a ia aaea?oueny
io?eiaoe a?aeiieie niiniaaie. Na?aae iiaeo iio?aeieo acie?a oa acei?a
ciaeaeaii i?aia?aoe c aenieith ooia?oeeaeiith, aa?a?oeeaeiith oa
aaeoa?eoeeaeiith aeoeai?noth, ui noeioeth? ?ioa?an aei ?o iiaeaeueoiai
aea/aiiy.
NIENIE IIOAE?EIAAIEO I?AOeUe CA OAIITH AeENA?OAOe??:
Oa?/aiei I.A. (-Aoeeeai?iicai?uai? a?i?enoeueoiie oa ?o iio?aei? –
iacai?ii? ?aaaaioe a neioacao acie?a oa acei?a (Iaeyaeiaa noaooy) //
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(oiceeeieiieiaei)aaicieii e eiiaeainaoeey noeueoaiaieaeia n oei?aeai. 17
Ananithciay eiio. neioac e ?aaeoe. niiniaiinoue i?aaie/aneeo niaae.
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aeeoei?aoeaoaeueaeaaeaea n ii/aaeiaie e oi?iaieaeii // 2-y eiio.
iieiaeuo o/aiuo-oeieeia. Oacenu aeieeaaeia.- Aeiiaoee,1990.-N.169.
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Cya?aa A.N., Ieo?ioei A.TH., Oa?/aiei A.A. ?aaeinaeaeoeaiua
oeeeeieiiaeinaoeee ia iniiaa
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2 Eenaeaa A.A., Naoa?ia N.I., ?oaeaiei A.A., Oa?/aiei A.A.
Acaeiiaeaenoaea i?iaeoeoia ina?iaiey iieeoei?yoeeaieaeia n
yeaeo?ioeeueiuie ?aaaaioaie // 3-y eiio. iieiaeuo o/aiuo-oeieeia. Oacenu
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Naoa?ia N.I., Cya?aa A.N., Oa?/aiei A.A.
N-(1-Oicee-2,2,2-o?eoei?iaoee)eieiioinaai – iiaue ?aaaaio oiieiai
i?aaie/aneiai neioaca // OVI Oe?a?inueea eiioa?aioe?y c i?aai?/ii?
o?i??. Oace aeiiia?aeae.- Oa?iii?eue,1992.- N.214.
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Chemistry of Sulfur. Abstracts.- Merseburg, 1994.- P. 274.
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(-acylaminosubstituted vinylsulfones // Oai aea.- P. 297.
Zyabrev V.S., Kiselev V.V., Kharchenko A.V., Drach B.S.
N-Arylsulfonyl-methylimidoylisothiocyanates – new reagents for
heterocyclization // Oai aea.- P. 299
Kiselev V.V., Zyabrev V.S., Kharchenko A.V., Drach B.S. Regioselective
heterocyclizations on imidiylalkylating agents and their analogs // 15th
International Congress of Heterocyclic Chemistry. Abstracts.-. 1995,
Taipei.- P. 03-253.
Oa?/aiei I.A., Naoa?ia N.I., ?oaeaiei ?.I., Eenaeueia A.A., Naaaiaiei
N.A. Aea/aiiy aaoa?ioeeee?caoe?e ia iniia? i?iaeoeo?a ai?aeiaee?eoaaiiy
niieoe aeaioaaeaioii? n??ee oa ?o iio?aeieo // XVII Oe?a?inueea
eiioa?aioe?y c i?aai?/ii? o?i??. Oace aeiiia?aeae.- Oa?e?a, 1995.- N.
30.
Ae?a/ A.N., A?iaa?aoeue A.N., Oa?/aiei I.A., Niie?e I.A. Ia?iaeoeai?
?aaaaioe c ai?aeiei ca’yceii aeey neioaco ooieoe?iiaeueieo iio?aeieo
acioenoeo aaoa?ioeeee?a // Oe?a?inueea eiioa?aioe?y “O?i?y acioiai?nieo
aaoa?ioeeee?a”. Oace aeiiia?aeae.-Oa?e?a, 1997.-N.7.
Oa?/aiei A.A. ?-Aoeeeai?iicai?uai? a?i?enoeueoiie oa ?o iio?aei? –
iacai?ii? ?aaaaioe a neioacao acie?a // XVI?I Oe?a?inueea eiioa?aioe?y c
i?aai?/ii? o?i??. Oace aeiiia?aeae.- Aei?i?iiao?ianuee, 1998.- N.53.
Aeaeaeae ?.I., A?iaa?aoeue A.N., Aeiia?aaeiaa O.E., I?euei N.A, Eoe?o
I.TH, Oa?/aiei A.A. C?o/iee i?aeo?ae aei neioaco
ooieoe?iiaeueii-cai?uaieo aeueaeaa?ae?a ienacieueiiai ?yaeo // Oai aea.-
N.83.
?oaeaiei ?.I., Iieoeyo E.N., Eenaeueia A.A., Oa?/aiei I.A.
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(-aoeeeai?iia?i?e-noeueoii?a // Oai aea.- N. 248.
Iieoeyo E.N., ?oaeaiei ?.I., Eenaeueia A.A., Oa?/aiei I.A.
Oeeeei-eiiaeainaoe?y 1-oicee-2-oei?aoai?eai?ae?a ea?aiiiaeo eeneio c
N-a?eeo?i-na/iaeiaie // ? ?aa?iiaeueia eiioa?aioe?y iieiaeeo a/aieo oa
nooaeaio?a c aeooae. ieoaiue o?i??. Oace aeiiia?aeae.
–Aei?i?iiao?ianuee, 1999.- N.15.
Oa?/aiei A. A. I?eiaiaiea S-aieaeiaeeeee?iaaiey a neioacao
ooieoeeiiaeueiuo i?iecaiaeiuo acioenouo aaoa?ioeeeeia.- ?oeiienue.
Aeenna?oaoeey ia nieneaiea o/aiie noaiaie aeieoi?a oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.03 – i?aaie/aneay oeiey .- Oe?aeineee
ainoaea?noaaiiue oeieei-oaoiieiae/aneee oieaa?neoao, Aeiai?iiao?iane,
1999.
Aeenna?oaoeey iinayuaia nenoaiaoe/aneiio enneaaeiaaieth ?iee
S-(-aieaeiaeeeee?iaaiey, S-(-aieaeiaeeaieee?iaaiey e ?iaenoaaiiuo
i?ioeannia a aaia?aoeee ooieoeeiiaeece?iaaiiuo aoeeeee/aneeo e iniaaiii
aaoa?ioeeeee/aneeo nenoai. Ia iniiaa aeinooiiuo N-(oei?iaoee)aieaeia,
N-(iieeoei?aeeee)aieaeia e iaianuuaiiuo aceaeoiiia ?ac?aaioaiu oaeiaiua
i?aia?aoeaiua niiniau neioaca ?aciiia?aciuo i?iaeoeoia
S-(-aieaeiaeeeee?iaaiey e S-(-aieaeiaeeaieee?iaaiey, eioi?ua a naith
i/a?aaeue oaeaeinue eniieueciaaoue aeey iieo/aiey niioaaonoaothueo
(-noeueoiieecaiauaiiuo eieaeieeoei?eaeia, ecioeeaiaoia, ecioeioeeaiaoia
e ea?aiaeeeieaeia. Ana yoe iieeoeaio?iaua ?aaaaiou ieacaeenue
i?eaiaeiuie aeey ?yaea aaoa?ioeeeeecaoeee, eioi?ua i?eaaee e iiaui
i?iecaiaeiui ?aciiia?aciuo acieia e aceiia. Oae,
1-a?eenoeueoiiee-2,2-aeeoei?aiaieaeu oe?iei eniieueciaaiu aeey neioaca
iiauo aeeooieoeeiiaeueiuo i?iecaiaeiuo ienaciea, eioi?ua niaea?aeao a
iieiaeaiee 4 a?eenoeueoiieeueioth a?oiio, a a iieiaeaiee 5 ia iaiaa
aaaeiua ooieoeeiiaeueiua caianoeoaee: ia?eaioia?oiio, iaoeeoeia?oiio,
aeeee- e aeeaeeeeaieiia?oiiu. E?iia oiai, a iieiaeaiea 2 oaeeo ienacieia
oaeaeinue aaanoe ?aaeoeeiiiiniiniaioth oi?ieeueioth a?oiio e iieo/eoue
iiaua oeiu 2,4,5-o?eooieoeeiiaeeciaaiiuo ienacieia. Aeey neioaca
iiaeiaiuo i?iecaiaeiuo oeaciea aia?aua eniieueciaaiu
1-a?eenoeueoiiee-2,2-aeeoei?yoaieeecioeioeeaiaou, eioi?ua eaaei
acaeiiaeaenoaotho n ia?ae/iuie e aoi?e/iuie aieiaie e aeatho n aunieei
auoiaeii iaecaanoiua ?aiaa 2-aeeeeaieii- e
2-aeeaeeeeaieii-4-a?eenoeueoiiee-5-oei?oeacieu. Aianoa n oai, aeey
iieo/aiey i?iecaiaeiuo 4(5)-oaieenoeueoiieeeieaeaciea aia?aua oaeaeinue
i?eiaieoue i?eaeiaeueiue ?aaaaio –
N,N-aen(1-oaieenoeueoiiee-2,2-aeeoei?yoaiee)ea?aiaeeeieae, eioi?ue
naiaia?acii oeeeeecoaony i?e iineaaeiaaoaeueiie ia?aaioea aai
a?iiaoe/aneeie e aeeoaoe/aneeie aieiaie. I?e yoii, e?iia ia?aciaaiey
eieaeacieueiiai eieueoea, i?ioaeaao iea?aoeey oaieenoeueoiieeueiiai
inoaoea, /oi iiaeoaa?aeaeaii i?e iiiiue ?aioaaiino?oeoo?iuo
enneaaeiaaiee.
Ia iniiaa iiauo N,S-?aaaaioia, eioi?ua oanii naycaiu n i?iaeoeoaie
S-(-aieaeiaeeeee?iaaiey, oaeaeinue neioace?iaaoue oaeaea ?yae
i?iecaiaeiuo s-o?eaceia e 2I-1,3,5-oeaaeeaceia. N?aaee iiauo
ooieoeeiiaeueiicaiauaiiuo acieia e aceiia iaeaeaiu niaaeeiaiey n aunieie
ooiaeoeeaeiie, aa?aeoeeaeiie e aaeoa?eoeeaeiie aeoeaiinoueth, /oi
noeioee?oao eioa?an e eo aeaeueiaeoaio eco/aieth.
Oniaoiiio i?eiaiaieth i?iaeoeoia S-(-aieaeiaeeeee?iaaiey e eo aiaeiaia
a ?acee/iuo aniaeoao i?aaie/aneiai neioaca niinianoaiaaei enneaaeiaaiea
?yaea iaueo i?iaeai, eioi?ua eanathony:
?iee ?-yooaeoa a ?iaenoaaiiuo nenoaiao SII-, SIV- e SVI-
aieaeiaeeeee?iaaiey;
aeeyiea i?ioio?iiee ia noa?aioeie/aneee ?acoeueoao ioeeaioeeueiiai
caiauaiey a aiaieaeao;
caaeneiinoe ?aaeinaeaeoeaiinoe eieaeieeaeeeee?iaaiey aiaeaeaioiuo
N,S-ioeeaioeeia io neiiao?e/iinoe no?oeoo?u ?aaeoaioia, i?e?iaeu
yeaeo?ioeeueiuo oeaio?ia a 2-acai?iiaiiaie o?eaaea, ioeeaiooaiinoe
iooiaeyuae a?oiiu e i?eioeeia “neiaeica”.
Eeth/aaua neiaa: S-(-aieaeiaeeeee?iaaiea, S-(-aieaeiaeeaieee?iaaiea,
S-eieaeieeaeeeee?iaaiea, (-noeueoiieecaiauaiiua aiaieaeu,
eieaeieeoei?eaeu e aaoa?ieoioeaiu, noeueoiieecaiauaiiua acieu,
ooieoeeiiaeece?iaaiiua aceiu.
Oa?/aiei I. A. Canoinoaaiiy S-ai?aeiaee?ethaaiiy a neioacao
ooieoe?iiaeueieo iio?aeieo acioenoeo aaoa?ioeeee?a.- ?oeiien.
Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy aeieoi?a o?i?/ieo iaoe ca
niaoe?aeuei?noth 02.00.03 – i?aai?/ia o?i?y. – Oe?a?inueeee aea?aeaaiee
o?i?ei-oaoiieia?/iee oi?aa?neoao, Aei?i?iiao?ianuee, 1999.
Aeena?oaoe?y i?enay/aia iiooeai iiaeo iai?yie?a canoinoaaiiy i?iaeoeo?a
S-(-ai?aeiaee?ethaaiiy oa ?o aiaeia?a a ??cieo aniaeoao i?aai?/iiai
neioaco aoeeee?/ieo ? iniaeeai aaoa?ioeeee?/ieo niieoe. Ia iniia?
i?ea?iaeueieo n??eiai?nieo ?aaaaio?a, eio?? i?noyoue aei oiai ae
aiai?aeio, ?i?aei?eoei?eaeio aai aaoa?ieoioeaiiao a?oio, aaeaeiny
?ic?iaeoe c?o/i? i?aeoiaee aei neioaco oaeeo ooieoe?iiaeueieo iio?aeieo
ienacieo, o?acieo, ?i?aeacieo, 1,2,4-o?aae?acieo, 1,3,5-o?eaceio,
1,2-aeea?ae?i-s-o?eaceio, 2I-1,3,5-o?aae?aceio oa ?ioeo aaoa?ioeeee?/ieo
nenoai, eio?? o a?eueoino? aeiaaee?a iaiiaeeeai io?eiaoe ?iaeoa. Na?aae
iiaeo iio?aeieo acie?a oa acei?a ciaeaeai? niieoee c aenieith
ooia?oeeaeiith, aa?a?oeeaeiith oa aaeoa?eoeeaeiith aeoeai?noth, ui
noeioeth? ?ioa?an aei ?o iiaeaeueoiai aea/aiiy.
Eeth/ia? neiaa: S-(-ai?aeiaee?ethaaiiy, S-(-ai?aeiaeeai?ethaaiiy,
S-?i?aei?eaee?ethaaiiy, (-noeueoii?ecai?uai? aiai?aee, ?i?aei?eoei?eaee
oa aaoa?ieoioeaie, noeueoii?ecai?uai? aciee, ooieoe?iiae?ciaai? aceie.
Kharchenko A.V. Application S-amidoalkylation in Syntheses of Functional
Derivatives of Nitrogen-Containing Heterocyclic Compounds.-Manuscript.
The dissertation for the degree of Doctor of Chemical Sciences,
speciality 02.00.03 – organic chemistry.- Ukrainian Chemical Engineering
State University, Dnepropetrovsk, 1999.
The dissertation is dedicated to the search for novel applications of
S-(-amidoalkylation products and their analogs in different domains of
organic synthesis of acyclic and particularly heterocyclic compounds.
Based on the original sulfur-containing reagents with enamide, imidoyl
chloride or heterocumulene groups, there have been developed the
convenient synthetic routes to functionalized of oxazoles, thiazoles,
imidazoles, 1,2,4-thiadiazoles, s-triazines,
1,2-dyhydro-1,3,5-triazines, 2H-1,3,5-thiadiazines and other
heterocyclic systems which are often impossible to prepare by other
methods. Compounds with a high fungicidal, herbicidal and bactericidal
activity were found among them which stimulates a further investigation
in this field.
Key words: S-(-amidoalkylation, S-(-amidoalkenylation,
S-imidoylalkylation, (-sulfonyl-substituted enamides, imidoyl chlorides
and heterocumulenes, sulfonyl-substituted azoles, functionalized azines.
– PAGE 2 -_
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