Oa?e?anueeee iaoe?iiaeueiee oi?aa?neoao ?i. A.I. ea?ac?ia
oaee 547.859 + 547.772.2
Iaiiiia ai?en aieiaeeie?iae/
eiiaeainiaai? aaoa?ioeeeee – i?iaeoeoe aca?iiae?? ae?ai?iiacie?a c
,-iaiane/aieie eaoiiaie
Niaoe?aeuei?noue 02.00.03 – i?aai?/ia o?i?y
aaoi?aoa?ao
aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy
eaiaeeaeaoa o?i?/ieo iaoe
Oa?e?a – 1999
Aeena?oaoe??th ? ?oeiien
?iaioo aeeiiaii ia eaoaae?? i?aai?/ii? o?i?? Oa?e?anueeiai
iaoe?iiaeueiiai oi?aa?neoaoo ?i. A.I.Ea?ac?ia
Iaoeiaee ea??aieeAeioeaio eaoaae?e i?aai?/ii? o?i?? Oa?e?anueeiai
iaoe?iiaeueiiai oi?aa?neoaoo ?i. A.I.Ea?ac?ia, eaiaeeaeao o?i?/ieo iaoe,
aeioeaio Eiein Iaae?y Ieeiea?aia
io?oe?ei? iiiiaioeI?ioani? eaoaae?e i?aai?/ii? o?i?? Oe?a?inueeiai
aea?aeaaiiai o?i?ei-oaoiieia?/iiai oi?aa?neoaoo, aeieoi? o?i?/ieo iaoe,
i?ioani? I?inyiee Ieaenaiae? Aaneeueiae/
(i. Aei?i?iiao?ianuee)
Noa?oee iaoeiaee ni?a?ia?oiee 7-ai a?aeae?eo ?inoeoooo iiiie?enoae?a
IAI Oe?a?ie, eaiaeeaeao o?i?/ieo iaoe,
n.i.n. Iaoeaiea? Eaii?ae Aeaa?aeiae/
(i. Oa?e?a)
i?ia?aeia onoaiiaaO?ceei-o?i?/iee ?inoeooo
?i. I.A. Aiaaonueeiai IAI Oe?a?ie, a?aeae?e iieaeoey?ii? no?oeoo?e oa
niaeo?ineii??
(i. Iaeana)
Caoeno aeena?oaoe?? a?aeaoaeaoueny “_3_” aa?aciy 2000 ?. i 1600 aiae.
ia can?aeaii? niaoe?ae?ciaaii? a/aii? ?aaee Ae 64.051.14 Oa?e?anueeiai
iaoe?iiaeueiiai oi?aa?neoaoo ?i. A.I.Ea?ac?ia (ie. Naiaiaee, 4, aoae.
7-80)
C aeena?oaoe??th iiaeii iciaeiieoenue o Oeaio?aeuei?e iaoeia?e
a?ae?ioaoe? Oa?e?anueeiai iaoe?iiaeueiiai oi?aa?neoaoo ?i. A.I.Ea?ac?ia
Aaoi?aoa?ao ?ic?neaii “27” n?/iy 2000 ?.
A/aiee nae?aoa?
niaoe?ae?ciaaii? a/aii? ?aaee E.I. Eia?iiaa
Caaaeueia oa?aeoa?enoeea ?iaioe
Aeooaeuei?noue aeine?aeaeaiiy A?eueo?noue aeine?aeaeaiue a aaeoc? o?i??
aaoa?ioeeee?/ieo niieoe iia’ycaii c ?ic?iaeith iiaeo iaoiae?a oi?ioaaiiy
oeeeeo. Aeaye? eeane/i? iaoiaee, ye ? ?ai?oa, oe?iei aeei?enoiaothoueny,
aea iino?eii ?nio? iaiao?aei?noue a noai?aii? aenieiaoaeoeaieo iaoiae?a
neioaco iiaeo iio?aeieo oa iaoiae?a i?iaaaeaiiy ?aaeoe?e a i’yeeo
oiiaao.
A oie aea /an, ii?yae c neioacii iiaeo o?i?/ieo niieoe, iaiao?aeiei ?
ooi/iaiiy aeaieo i?i ia?aa?a ?aaeoe?e, aeine?aeaeaieo ?ai?oa, ?
inoaoi/ia anoaiiaeaiiy no?oeoo?e i?iaeoeo?a. A ca’yceo c oeei, aea/aiiy
?aaeoe?e iae?ai?iiacie?a, ui i?noyoue N-ai?iia?oio c a,b-iaiane/aieie
eaoiiaie ? ?o iio?aeieie, ? aeooaeueiith i?iaeaiith.
?ioa?an aei oaeeo aeine?aeaiue caa??aa?oueny ua e oiio, ui i?iaeoeoe
aeuacaaaeaieo ?aaeoe?e, iiaeooue ciaeoe i?aeoe/ia aeei?enoaiiy ye
o?c?ieia?/ii-aeoeai? ?a/iaeie (aioe-NI?Ae, aioea?ioeee, iae?ieaioeee ?
aioeaeai?anaioe), aa?aieee ? ethi?iioi?e.
Ca’ycie ?iaioe c iaoeiaeie i?ia?aiaie, ieaiaie, oaiaie: Ai?iaeiaae
inoaii?o ?ie?a eieaeoeaii eaoaae?e i?aai?/ii? o?i?? Oa?e?anueeiai
iaoe?iiaeueiiai oi?aa?neoaoo i?iaiaeyoueny nenoaiaoe/i? aeine?aeaeaiiy
?aaeoe?eii? caeaoiino? a?iiaoe/ieo oa aaoa?ioeeee?/ieo i-ae?ai?i?a
a?aeiinii ??ciiiai?oieo a?aeaeo?io?eueieo ?aaaaio?a, a ia?oo /a?ao, oea
noino?oueny 1,3-ae?a?eei?iiaiii?a (oaeeii?a) oa ?o a,b-aeea?iiiio?aeieo.
I?aaenoaaeaia aeena?oaoe?eia ?iaioa ? neeaaeiaith /anoeiith ieaiiaeo
aeine?aeaeaiue eaoaae?e i?aai?/ii? o?i?? OAeO a iaaeao
aea?aeathaeaeaoii? IAe? “Iia? a?ieia?/ii aeoeai? ?a/iaeie ? aeieia?/ii
/eno? oaoiieia?? aeey iaaeeoeeie, n?euenueeiai ainiiaea?noaa ? caoenoo
iaoa??ae?a a?ae ooeiaeaeaiue”, ca?aeii iaeaco I?i?noa?noaa ina?oe
Oe?a?ie ?37 a?ae 13.02.97 ?, ? aea?ae?a?no?aoe?? 0197V008102.
Iaoa ? caaea/? aeine?aeaeaiiy iieyaaee a aea/aii? caaaeueieo
caeiiii??iinoae o?i?/ii? iiaaae?iee ?yaeo i-ae?ai?iiacie?a, ui i?noyoue
a?ae?aceiio ai?iia?oio, a ?aaeoe?yo c 1,3-ae?a?eei?iiaiiiaie oa ?o
a,b-aeea?iiiio?aeieie.
Aeey ae??oaiiy iinoaaeaieo caaea/ aoei iaiao?aeii:
-neioacoaaoe aeo?aei? 1,2-ae?ai?ii-4-a?ee?i?aeaciee,
1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacie, 3,4,5-o?eai?ii-1,2,4-o?eacie ?
1,5-ae?ai?iioao?acie.
-i?iaanoe neioac ? ?aeaioeo?eaoe?th i?iaeoeo?a aca?iiae?? aeu?caaaeaieo
ae?ai?i?a c a,b-iaiane/aieie eaoiiaie oa ?o iio?aeieie.
– anoaiiaeoe aca?iica’ycie i?ae aoaeiaith ? o?ceei-o?i?/ieie
aeanoeainoyie aeo?aeieo aeeai?i?a ?c iai?aaeaii?noth ia?aa?ao aca?iiae??
? no?oeoo?ith i?iaeoeo?a a ?aaeoe?yo, ui aeine?aeaeoaaeenue.
Iaoeiaa iiaecia: – Aia?oa io?eiaii aeea?ae?iiio?aei?
7-ai?ii-2,4,5-o?ea?ee?i?aeaci[1,5-b]i??eaeacei?a ?aaeoe??th i?ae
1,2-ae?ai?ii-4-a?ee?i?aeacieaie oa oaeeiiaie. Iieacaii, ui i?iaeoeoaie
?aaeoe?? aeacaieo aeua ae?ai?ii?i?aeacie?a c a,b-aeea?iiiio?aeieie
oaeeii?a, a-a?iioaeeiiaie, 1,3-ae?a?eei?ii?iiiaie ? aaoa?ia?iiaoe/i?
7-ai?ii-2,4,5-o?ea?ee?i?aeaci[1,5-b]i??eaeaceie.
-Anoaiiaeaii, ui aca?iiae?y 1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacieo c
1,3-ae?a?eei?iiaiiiaie oa ?o a,b-aeea?iiiio?aeieie
noi?iaiaeaeo?oueny ae?i?ioaaiiyi a?ae?aceiii? ai?iia?oie c ooai?aiiyi
6-iene-2,3-aeeoai?e-5,6-aeea?ae?i-5,7-ae?a?ee?i?aeaci[1,2-a]i??ei?aeei?a
, 6-iene-2,3-aeeoai?e-5,7-ae?a?ee?i?aeaci [1,2-a]-i??ei?aeei?a oa
2,3-aeeoai?e-5,7-ae?a?ee?i?aeaci[1,2-a]i??ei?aeei?a, a?aeiia?aeii.
Iieacaii, ui i?ioean ieeneaiiy aeea?ae?ino?oeoo?e ? aoi?eiiei.
-Cai?iiiiiaaii iaoiae neioaco noaa?eueieo nieae
1,2-ae?ai?iio?eaciei[1,5-a]- i??ei?aeei?y ?aaeoe??th
3,4,5-o?eai?ii-1,2,4-o?eacieo c a,b-aeea?iiiio?aeieie oaeeii?a oa
a-a?iioaeeiiaie. I?iaaaeaii o?i?/io iiaeeo?eaoe?y iaea?aeaieo niieoe,
aeine?aeaeai? iaci?iii? 1,2-ae?ai?iio?eaciei[1,5-a]i??ei?aeei?e-6-ieaoe.
-Anoaiiaeaii, ui 1,2-ae?ai?ii-4-a?ee?i?aeaciee,
1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacie oa 3,4,5-o?eai?ii-1,2,4-o?eacie a
?aaeoe?yo c oaeeiiaie oa ?o a,baeea?iiiio?aeieie aenooiathoue oeiiaeie
1,3-aeeioeeaio?eaie.
-Iieacaii, ui aeey 1,5-ae?ai?iioao?acieo a ?aaeoe?? ?c
1,3-ae?a?eei?iiaiiiaie, niinoa??aa?oueny ia?aa?oioaaiiy Ae?i?ioa c
ooai?aiiyi a?aeiia?aeieo
1-(5-oao?acie?e)-3,5-ae?a?eei??acie?i?a .
I?aeoe/ia cia/aiiy io?eiaieo ?acoeueoao?a: ?ic?iaeaii iaoiaee neioaco
iiaeo aaoa?ioeeee?/ieo niieoe acieiaceiiaiai ? acieiacei??aiai ?yaeo:
7-ai?ii-2,4,5-o?ea?ee-3,4-aeea?ae?i?i?aeaci[1,5-b]i??eaeacei?a ? ?o
aaoa?ia?iiaoe/ieo iio?aeieo,
2,3-aeeoai?e-5,7-ae?a?ee-6-iene-5,6-aeea?ae?i?i?aeaci[1,2-a]i??ei?aeei?a
, 2,3-aeeoai?e-5,7-ae?a?ee-6-iene?i?aeaci[1,2-a]i??ei?aeei?a,
2,3-aeeoai?e-5,7-ae?a?ee- ?i?aeaci[1,2-a]i??ei?aeei?a,
1,2-ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e a?ii?ae?a,
1,2-ae?ai?ii-5-(i-i?o?ioai?e)-7-a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e-6
-ieao?a ? 5-(3,5-aeea?ee-4,5-aeea?ae?i-1-i??acie?e)-1I-oao?acie?a.
Aoaeiaa iieaeoe a?eueoino? io?eiaieo ?a/iaei aeicaiey? cae?enieoe ?o
neioaoe/io iiaeeo?eaoe?th oeyoii aaaaeaiiy oa?iaeioi?ieo a?oi. Oea
a?aee?eaa? iia? ia?niaeoeae aeey iiooeo na?aae neioaciaaieo ?a/iaei
o?c?ieia?/ii aeoeaieo niieoe.
Iniaenoee aianie aaoi?a iieyaa? a ieaioaaii? oa i?iaaaeaii?
neioaoe/iiai aenia?eiaioo, ?ic?iaoe? iaoiae?a neioaco iiaeo
aaoa?ioeeee?/ieo nenoai, ?acoeueoaoii /iai noaa neioac 69 iaiienaieo a
e?oa?aoo?? niieoe, ?aeaioeo?eaoe?? io?eiaieo niieoe niaeo?aeueieie
iaoiaeaie, i?aeaioiaoe? c?ace?a aeey i?iaaaeaiiy ?NAe, iaaiai?thaaii?
io?eiaieo ?acoeueoao?a, oi?ioethaaii? aeniiae?a oa o/ano? o iinoaiiaoe?
caaea/ aeine?aeaeaiiy.
Ai?iaaoe?y ?acoeueoao?a aeena?oaoe?? a?aeaoeany ia XVII e XVIII
Oe?a?inueeeo eiioa?aioe?yo c i?aai?/ii? o?i?? (1995 ? 1998 ??),
I?aeia?iaei?e eiioa?aioe?? c o?i?? acioai?nieo aaoa?ioeeee?a 1997 ?,
I?aeia?iaei?e eiioa?aioe?? c i?aai?/ii? o?i?? ? eiia?iaoi?iiai neioaco
1999 ?, eiioa?aioe?yo iieiaeeo a/aieo Oe?a?inueeiai ?inoeoooo
oa?iaeioa?ai?? aiaeie?eiieo caoai?thaaiue ? Aei?i?iiao?ianueeiai
aea?aeaaiiai oi?aa?neoaoo (1998 ? 1999 ??), a oaeiae ia XVI
i?aeia?iaeiiio Iaiaeaea?anueeiio eiia?an? c caaaeueii? oa i?eeeaaeii?
o?i?? (1998 ?).
Ioae?eaoe??: ca ?acoeueoaoaie aeena?oaoe?? iioae?eiaaii 3 noaoo? ? 6
oac aeiiia?aeae ia oe?a?inueeeo, i?aeia?iaeieo ? ?aa?iiaeueieo
eiioa?aioe?yo.
No?oeoo?a ? ianya ?iaioe: Aeena?oaoe?y neeaaea?oueny c? anooio, o?ueio
iniiaieo ?icae?e?a, aeniiae?a, nieneo e?oa?aoo?e (111 aeaea?ae) oa
aeiaeaoeo. Caaaeueiee ianya ?iaioe neeaaea? 136 noi??iie, i?noeoue 21
oaaeeoeth, 15 ?enoie?a. Aeiaeaoie neeaaea?oueny c 5 oaaeeoeue.
Ci?no ?iaioe
1. Aca?iiae?y 1,2-ae?ai?ii-4-a?ee?i?aeacie?a c 1,3-ae?a?eei?iiaiiiaie
oa ?o iio?aeieie
1.1 Neioac aeea?ae?iiio?aeieo
7-ai?ii-2,4,5-o?ea?ee-?i?aeaci[1,5-b]i??eaeacei?a
Eei’yo?iiy aea?iieaeoey?ieo e?eueeinoae 1,2-ae?ai?ii-4-a?ee?i?aeacieo
oa a?aeiia?aeiiai 1,3-ae?a?eei?iiaiiio a nie?o? a i?enooiino?
eaoae?oe/ieo e?eueeinoae o?aoe/ieo ai?i?a aeicaiey? aeae?eeoe c
caaeia?eueieie aeoiaeaie niieoee IX – XIII
wmetafile8? ??„f????????????????????zOe
???uOy??????1/4????Journal??a???-?????.????E3/4???&
?
???u?????yyy?”????-????ue???????????-????$?AF1/4FI&N
&AF
???u??????????”????-????ue??yyy??????-?????&??IV-VIII???
?????? ?G?????i?????eD „ ??IX-XIII?????????
A#ae?????i?????(#aA’6??XIV-XVI?????????8I?????i??????I
‚??XVII, XVIII?????????„a???????????eae‚n??XIX???
??????‚
b?????n?????e
h‚!3/4??XX-XXII?????????Aae?????o?????.eEOe??XI??
??????—?????o?????p–d??XXV???????;?
?a?????o?????p(an??1???????;? ?o ?????o??????
od??2???????;? ???????oe?????4¤^??3???????;?
?[U?????/?????oib4??4???????;?
??i?????o?????No3/4>??5???????;?
?Z!?????u???????`???6???????;?
?ei?????u?????x|eA??7?????Times New
Roman?;Journal?Symboll???????yy????yyyy????yy????yyyy????yyyy??yy?
?&??MDLSK????E??Times New Romanx??!??A·D?@?D?
C6H4-R’-p?!????D??‘D? ‘?????!??A·D?? D?
‘???(??!????D???D? ‘????!??A·D??3/4D?C6H4-R”-p?
‘????!??A?D???D??? ‘?? ?(??!?? 4E??D?!??
?!?? CE??D???!?? CE?????!??
?!?? 4E???
'???? '???.?(?? '???? '???? '???? '?
???!??aIE??ED?!?? FE??%D???!???>E??*D? ‘????
‘???(?? ‘???? ‘???(??!??A7E??D? p-R-C6H4^?
‘??
??!???RE??OD??%??b?? ‘?? ??!??a:E???D?p-”R-C6H4^?
‘??”??!?? -E??JD?p-‘R-C6H5^? ‘??$??!?? E? %E?!??
E??*E?!?? (E? %E???!?? (E??E???!?? E? E?!??
E??E? ‘?&?’?? ‘?’?(?.?(?? ‘?(?)?? ‘?)?*?? ‘?*?+??
‘?&?+??!??`.E?@E?!?? *E?AE???!???”E?`E? ‘?)?2??
‘?2?3?(?? ‘?3?4?? ‘?*?4?(??!??@ E?AE? p-MeC6H4^?
‘?4?9??!???6E?AE???NHAc????!???'E??ID???!?
?AE?@?D?!?? #E?@?D?!???'E?@°D??? '????? '????
'???(??
'?????!??A·D?@?D?"?????????3????4?NHAc6?=???
'?2?;??!??
E?A2E??>??Ph????!???ED??YC?!???ED??eC?!???UD??D
?!??AeD??eC?!??AeD??YC?!???UD??‚C? ‘????(?? ‘????
‘???(?? ‘???? ‘???(?? ‘?????
‘?????!??A·D?@?D?”?????????3????4?Ph6?=???
‘?’?=??!?? E? E? p-BrC6H4^? ‘?+????!???‰E??wD?!??8
c?G?C?????1/4o‡?…tM?????M??A???Times New
Roman?I?I?Li‰?*???Timer?X?I?X?? ?2
ac?O?K?????1/4o‡?…tM?????M??A???Times New
Roman?A?? ‰?,?‰?*???r?X?X?-?X?X?I?I?? ?ooe
pF?E?A?????1/4o‡?…tM?????M??A???Times New Roman?*???Times New
Ror?X?I?? ?J–0ae?G?C?????1/4o‡?…tM?????M??A???Times New
Roman?*???Times New Ror?X?X?V?? ?”c1/4
TH?C???????1/4o‡?…tM?????M??A???Journal?w Roman?*???Times New
RoU?1?? ?.0j?C???????1/4o‡?…tM?????M??A???Journal?w
Roman?*???Times New RoU?2?? ?,
8?C???????1/4o‡?…tM?????M??A???Journal?w Roman?*???Times New
RoU?3?? ?u??C???????1/4o‡?…tM?????M??A???Journal?w
Roman?*???Times New RoU?4?? ?|”¤
AE?C???????1/4o‡?…tM?????M??A???Journal?w Roman?*???Times New
RoU?5?? ?Xav ?C???????1/4o‡?…tM?????M??A???Journal?w
Roman?*???Times New RoU?6?? ?1/4?ae
ae?C???????1/4o‡?…tM?????M??A???Journal?w Roman?*???Times New
RoU?7???]??&?°DARC-F1?CHEMDRAW 4.0 991102200700????e?X?
????·?!?????C ??????????? ???C ???·?/?? ???????C
??????a?????????? ???X? ????·?I?????O ????‘?a?? ???C
???·'?????????C ????I????? ? ???????N ????a'??
???????N ????a?? ????????????C ????IL?????????? ???C
???·??????????????C ????oQ?????? ???????N
????eg?? ???????C ????Oe?????? ???????X?
????Av?????N ???I?????X? ????E?????X? ????cL?
????C ???^?????????C ????s?????? ???????N
??????? ???????N ?????*?????????????C
????s6????????? ? ???C ???^*????????? ????C
????›:?????? ???
????N ????‘Q?? ??? ????C ????xN?????? ???????X?
????g`? ????N ???µ5?????"????C ????se??$?
???(????????X? ????H6?????C ???a@?"????C
????CG?!????#? ???
????O ????A`?"? ???C ???]Y??? ???%????C
???]A??$????&? ???C ???s¶??%? ???'????C ????A??&????(?
???C ????Y??'? ???????C ???E,?*????.? ???C ????a
?)????+? ???4????N ????/,?*? ???,????N
????/E?+????-????/????C ????aR?,????.????1? ???C
????EE?-????)? ???5????C ???? U?,????0? ???3????N
????yl?/? ???1????C ????aei?0????-? ???2????X?
????O?1????N ??? O?/????X? ????a?*????X?
????¶R?.????C ????,?o?7? ???:???????N ????&??6?
???8????C ??????7????9? ???;????C ????o?8? ???:????N
?????a?9????6????=????X? ??????!?8????N ???C?i?6????N
????I?:????C ????>’???? ???B????D????N ????7«??>?
???@????C ????«???????A? ???C????C ???’??@? ???B????N
????)???A????>????E????X? ????A??@????N ???V???>????N
????)j??B????F? ???C ???)Q??E? ???G????X? ????:@??F????C
????T©??L? ???P????I????C ????k·??H????J????K? ???C ???
IV R’ = R” = H;; V R’ = OCH3, R” = H;; VI: R’ = Br, R” = H;; VII R’ =
NO2, R” = H;; VIII R’ = F, R” = 2-OH; IX, XIV R = Me, R’, R” = H; X, XV
r = r’ = me, r” = h; xi R= me, R’ = Br, R” = H; xii, xvi r = h, r’ =
no2, R” = h; XIII r = Br, r’ = h, r”= 2-oh
A ?o ?* niaeo?ao, ciyoeo a oaaeaoeao EBr, iathoue i?noea nioae a iaeano?
1637 ni-1, a oaeiae aea? nioae aeecueei 3270 ? 3450 ni-1. Ne?ae
caoaaaeeoe, ui nioaa i?e 3400 ni-1 ? oe?ieith ? iaei?ioaineaiith, ?? ia
iiaeia iaeiicia/ii ?aeaioeo?eoaaoe c n asNH2 . A niaeo?ao II?
neioaciaaieo niieoe, ciyoeo a AeINI-D6, niinoa??aa?oueny oeiiaa AAO
nenoaia: aeaa aeoaeaoe aeoaeao?a i?ioii?a iaoeeaiiai? a?oie a iaeano?
3,0 i.ae. ? 3.5 i.ae. a?aeiia?aeii, ? aeoaeao aeoaeao?a iaoeiiaiai
i?ioiio c d = 4,5i.ae. (2JAB= -12-14, 3JAX= 8,1, 3JBX= 2,8 Aoe). E??i
oiai, a niaeo?ao aeyaey?oueny ?icoe?aiee neiaeao c o?i?/iei cnoaii
aeecueei 6 i.ae., yeee cieea? i?e i?iaaaeaii? aeaeoa?iiai?io, oa
ioeueoeieao a?iiaoe/ieo i?ioii?a a iaaeao 7-8 i.ae., ?ioaa?aeueia
?ioaineai?noue yeiai, na?ae/eoue i?i caa?aaeaiiy a niieoeao IX – XIII
o?ueio a?iiaoe/ieo yaea?.
I?e eei’yo?ii? a ioeoiaiio aia?ae?eae? niieoee XI io?eiaii aoeeeueia
iio?aeia XXV. Eiai ?* oa II? niaeo?e na?ae/aoue i?i iayai?noue aoi?eiii?
ai?iia?oie oa aoeaoeeueii? a?oie (nNH= 3310 , nCO= 1678 ni-1, dCH3= 2,3,
dNH= 6,03 i.ae.). Oaeei /eiii, io?eiai? aeai? i?aeoaa?aeaeothoue
caa?aaeaiiy ia?aeiii? ai?iia?oie a oe?eueiaeo i?iaeoeoao IX -XIII.
Inoaoi/ii no?oeoo?o neioaciaaieo niieoe aoei c’yniaaii ca aeiiiiiaith
?NA aeey i?iaeoeoa X, yeee ?
7-ai?ii-2,4,5-o?ea?ee-3,4-aeea?ae?i?i?aeaci[1,5-b]- i??eaeaceiii. Iiaia
aiaeia?y a niaeo?aeueieo oa?aeoa?enoeeao niieoee O oa niieoe IX, XI –
XIV aeicaiey? noaa?aeoaaoe, ui inoaii? iathoue oo ae naio
aaoa?ioeeee?/io no?oeoo?o, a ia no?oeoo?o ?i?aeaci[3,4-b]o?eacai?ia, ye
aaaaeaeiny ?ai?oa.
Ioaea, i?e iayaiino? a iieaeoeao ae?ai?i?a ? – ??? /ioe?ueio
iioaioe?eieo ioeeaio?eueieo oeaio??a, iaea?eueo ?aaeoe?eiicaeaoiei ?
aoii N5 ?i?aeacieueiiai oeeeeo. Naia ii iueiio i?ioiaeeoue ?aaeoe?y
b-aaoa?eethaaiiy iaiane/aiiai eaoiia c iine?aeoth/ith oeeee?caoe??th ii
a?ae?aceii?e ai?iia?oi?.
I?e i?iaaaeaii? ?aaeoe?e ae?ai?i?a ? – ??? c oaeeiiaie IV-VIII a
aeeiaoeeoi?iai?ae?, ii?yae ?c niieoeaie IX – XIII, niinoa??aa?oueny
ooai?aiiy i?iaeoeo?a ?o aaoa?ia?iiaoecaoe?? (XIV-XVI). A?iiaoecaoe?y
niieoe IX – XIII niinoa??aa?oueny oaeiae i?e o?eaaeiio eei’yo?ii?
inoaii?o a aeeiaoeeoi?iai?ae? /e i??eaeei?. Aoaeoeaia a?iiaoecaoe?y
a?aeaoaa?oueny i?e aeei?enoaii? nenoaie n??ea-i??eaeei.
Ni?iae iaea?aeaoe 7-ai?ii-2,4,5-o?ea?ee-3,4-aeea?ae?i?i?aeaci[1,5-b]-
i??eaeaceie a ?acoeueoao? o?ueioeiiiiiaioii? eiiaeainaoe??,
aeei?enoiaoth/e ae?ai?ie ? – ??? oa neioaoe/i? iiia?aaeieee oaeeiio –
a?iiaoe/i? aeueaeaa?aee oa aoeaoioaiii, ia iaee oni?oo ? i?ecaaee eeoa
aei oi?ioaaiiy a?ae?acii?a OO – OO??.
1.2 Neioac aaoa?ia?iiaoe/ieo iio?aeieo
7-ai?ii-2,4,5-o?ea?ee-?i?aeaci[1,5-b]i??eaeacei?a
Iaie iieacaii, ui ?aaeoe??th 1,2-ae?ai?ii-4-a?ee?i?aeacie?a ?-??? c
oaeeiiaeea?ii?aeaie XXVI-XXXI, a-a?iioaeeiiii XLIV oa 1,3ae?a?ee-
i?iiaiiiaie XLVII i L a noaiaea?oieo oiiaao (eei’yo?iiy a iaoaiie? a
oiiaao eaoae?co o?eaoeeai?iii) io?eiaii
7-ai?ii-2,4,5-o?ea?ee?i?aeaci[1,5-b]- i??eaeaceie XVI, XXXII-XXXVIII,
XLV, XLVIII ? LI ? a?aeiia?aei? oaeeiie, ui na?ae/eoue i?i o/anoue
o?aoeiieo ai?i?a a a?aeiiaeaii? i?ii?aeieo a-a?iioaeeii?a.
Iaiao?aeii a?aei?oeoe, ui a ?aaeoe?th c ae?ai?iaie ?-??? aaeaeiny
aaanoe o?eueee 3(i-i?o?ioai?e)-1-a?ee-2,3-aeea?iii?iiaiiie. Oea
coiiaeaii, ye a?eueo aenieith oaeaee?noth ae?i?ioaaiiy iieaeoee IAr, oae
? a?eueoith iiey?ecaoe??th N=N ca’yceo a?aeiia?aeiiai a-a?iioaeeiio.
wmetafile8? ??i5??????????????’-????
9i???uAEy??????1/4????Journal??a???-?????.????1/2‚?
??O?
???u?????yyy?”????-????ue???????????-????$??1/2„1/2?O
?O?O?1/2
???u??????????”????-????ue??yyy??????-????Ay???* XXVI
– XXXI Ar = 4-NO2-C6H4; xxvi, xxxix Ar’ = Ph; XXVII, XL Ar’ =
4-NO2-C6H4; XXVIII, XLI Ar’ = o??i?e, XXIX, XLII Ar’ 4-Cl-C6H4; XXX,
XLIII Ar’ 4-Br-C6H4; XXXI Ar’= 5-Br-o??i?e; XLIV, XLVI Ar 4-Cl-C6H4, Ar’
= Ph; XLVII, XLIX Ar’ = 4-OMe-C6H4; L, V Ar = 4-OMe-C6H4, Ar’ = Ph; XVI
R = H, Ar = 4-NO2-C6H4, Ar’ = Ph; R = H, Ar = 4-NO2-C6H4, Ar’ = o??i?e;
XXXIV R = Br, Ar = 4-NO2-C6H4, Ar’ = Ph; XXXV XXXII R = H, Ar =
4-NO2-C6H4, Ar’ = 4-NO2-C6H4; XXXIII R=Br, Ar = 4-NO2-C6H4, Ar’ =
4-Cl-C6H4; XXXVI R=Br, Ar = 4-NO2-C6H4, Ar’ = 4-Br-C6H4; XXXVII R=Br, Ar
= Ar’ = 4-NO2-C6H4; XXXVIII R=Br, Ar = 4-NO2-C6H4, Ar’ = 5-Br-o??i?e;
XLV R = Me Ar = 4-Me-C6H4, Ar’ = Ph; XLVIII R = H, Ar = 4-NO2-C6H4, Ar’
= 4-OMe-C6H4; LI R = Br, Ar = 4-Br-C6H4, Ar’ = Ph.
Aoaeiao niieoe XVI, XXXII-XXXVIII, XLV, XLVIII ? LI aeiaaaeaii iaoiaeaie
?* oa II? niaeo?ineii??. Oae, a ?* niaeo?ao neioaciaaieo niieoe XVI,
XXXII-XXXVIII, XLV, XLVIII ? LI niinoa??aathoueny aea? nioae i?e 3280 ?
3450 ni-1 a?aeianai? aei aaeaioieo eieeaaiue ia?aeiii? ai?iia?oie, a
oaeiae nioae a iaeano? 1630-1653 ni-1, ye? a?aeianai? aei noia?iiceoe??
aaeaioieo eieeaaiue N=N oa N=N ca’yce?a. A niaeo?ao II? niieoe XIV, XXXV
i LI niinoa??aa?oueny ?icoe?aiee neiaeao a iaeano? 6,5 i.ae. ui
aei??aith? aeaii i?ioiiai ? cieea? i?e i?iaaaeaii? aeaeoa?iiai?io oa
ioeueoeieao i?ioii?a a?iiaoe/ieo yaea? a iaeano? 6,8-8,4 i.ae, a oaeiae
neiaeao i?ioiio i??eaeaceiiaiai oeeeeo.
Inoaoi/ii no?oeoo?a neioaciaaieo i?iaeoeo?a aoea aeieacaia ca
aeiiiiiaith iaoiaeo ?NA ia i?eeeaae? niieoee XLV, yea aeyaeeanue
7-ai?ii-2,4,5-o?ea?ee?i?aeaci[1,5-b]i??eaeaceiii.
Iaeiioeii?noue niaeo?aeueieo oa?aeoa?enoee niieoee LXV oa an?o ?ioeo
i?iaeoeo?a ?yaeo aeicaiey? ?aeaioeo?eoaaoe inoaii? ye iio?aei?
7-ai?ii-2,4,5-o?ea?ee?i?aeaci[1,5-b]i??eaeaceio.
C iaoith anoaiiaeaiiy iinoaae?eiino? oi?ioaaiiy ?i?aeacii??eaeaceiiaiai
a?oeeeeo a neioaciaaieo niieoeao, iaie aoea aea/aia ?aaeoe?y a?ae?acii?a
OO, XLII, LIII c oaeeiiaeea?ii?aeii XVI. Eei’yo?iiy ?aaeoe?eii? noi?o?
aeicaieeei aeae?eeoe ?i?aeacii??eaeacei XVI. I?e oeueiio caaaeueia
oaeaee?noue i?ioeano oeeee?caoe?? caeiiii??ii iaaeaea a ?yaeo OO? ??X%?? ????????????c?????Z
???uAey??????1/4????Journal??a???-?????.????_???@
???u?????yyy?"????-????ue???????????-????$?=]=aB
?=]
???u??????????"????-????ue??yyy??????-????_=???2????
-????-????$?‹0‹5=a=]‹0???-????-????2‹???
_O???-????-????$?U]Ua‹5‹0U]???-????-????H
th???_U???-????-????$?thG?JUaU]thG???-????-
????Oaeei /eiii, 1,2-ae?ai?ii?i?aeaciee a ?aaeoe?yo c aiiiiaeie
nenoaiaie (oaeeiiaie, a,b-aeea?iioaeeiiaie ? b-aeeeaoiiaie) iiaiaeyoue
naaa ye oeiia? 1,3a?ioeeaio?ee, ui i?ecaiaeeoue aei oi?ioaaiiy
?i?aeaci[1,5-b]i??eaeaceiiaiai a?oeeeeo.
2. Aca?iiae?y 1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacieo c
1,3-ae?a?eei?iiaiiiaie oa ?o a,b-aeea?iioaeeiiaie.
Cai?uaiiy iaea?eueo ioeeaio?eueiiai oeaio?o a iieaeoe?
1,2-ae?ai?ii?i?aeacieo - aoiia N5 - oai?eueiei ?aaeeeaeii iiaeiii
ci?ithaaoe iai?yiie aaoa?ioeeee?caoe?? a ?aaeoe?? inoaiiueiai c
?iiiiaeie nenoaiaie.
Aeyaeeinue, ui i?iaaaeaiiy ?aaeoe?? 1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacieo
c 1,3ae?a?eei?iiaiiiaie a na?aaeiaeu? AeIOA iai?ioyc? o?ueio aiaeei
noi?iaiaeaeo?oueny ae?i?ioaaiiyi a?ae?aceiii? ai?iia?oie ? ooai?aiiyi
2,3aeeoai?e-5,7-ae?a?ee-6-iene-7,8-aeea?ae?i?i?aeaci[1,2-a]i??ei?aeei?a
LXI-LXIV. No?oeoo?a inoaii?o aeieacaia ca aeiiiiiaith ?* (nOH(CCl4):
3560 ci-1) ? II? niaeo?ineii??(d: 5,00 i.ae.(c. 6-CH); 5,30 i.ae. (c.
7-CH); 6,33i.ae. (c. IH); 6,70-8,22i.ae. (i. a?)). Ca aeiiiiiaith
INDOR-i?ioeaaeo?e ia i?eeeaae? no?oeoo?e LXIII aoei anoaiiaeaii, ui
ienea?oia ciaoiaeeoueny a 6-io iieiaeaii? a?oeeeeo. Neiaeao c o?i?/iei
cnoaii a iaeano? 5,0 i.ae. a?aeianaii aei NI i?ioiio a iieiaeaii? 6
aeea?ae?ii??ei?aeeiiaiai oeeeeo, neiaeao i?e 5,3-5,45 i.ae. - aei 5-I
i?ioiio. A?eueo o?eaaea iaa??aaiiy ?aaeoe?eii? noi?o? a nenoai? eneeie -
ioeoiaa eeneioa i?ecaiaeeoue aei a?aeiia?aeieo
2,3-aeeoai?e-5,7-ae?a?ee-6-iene?i?aeaci[1,2-a]- i??ei?aeei?a LXV, LXVI.
A oie aea /an a?iiaoe/i? iio?aei? ?i?aeacii??ei?aeeio LXVIII-LXX, ui ia
i?noyoue ienea?oie, aoee io?eiai? i?e o?eaaeiio eei'yo?ii?
1,2-ae?ai?ii?i?aeacieo c 3-(4-i?o?ioai?e)-1-a?ee-2,3-aeea?iii?iiaiiiaie
a iaoaiie? c aeiaaaeaie o?eaoeeai?io. Oeae i?ioean oaeiae
noi?iaiaeaeo?oueny a?aeuaieaiiyi a?ae?aceiii? ai?iia?oie
ae?ai?ii?i?aeacieo.
IV R=R'=H, VI R=Br, R'=H, VII R=NO2, R'=H, LIX R=H, R'=Br, LX R=NO2,
R'=CH3, XXVI R = H; XXX R= Br; LXVII R = OMe; LXI R = R' = H; LXII R =
H, R' = Br; LXIII R= Br, R' = H, LXIV R = NO2, R = H; LXV R= R' = H;
LXVI R = NO2, R' = Me, LXVIII R = NO2, R' = H; LXIX R = NO2, R'=Br; LXX
R = NO2, R' = OMe. .
Ooai?aiiy niieoe LXVIII-LXX eaea /a?ac ?ioa?iaae?ao, a yeiio i?ioean
aeea?ae?ia?iioaaiiy i?ioiaeeoue oaeaeoa, ai?ae noaae?y ieeneaiiy oa
ae?i?ioaaiiy a?ae?aceiii? ai?iia?oie.
I?enooi?noue a iieaeoeao LXI-LXIV aeaio o??aeueieo oeaio??a i?eionea?
iiaeeea?noue ooai?aiiy aeaio ae?anoa?aiia??a. Aea a?aenooi?noue o
niaeo?ao II? oeeo niieoe aeiaeaoeiaiai iiaeai?iiy iaeiioeiieo neaiae?a
aeaco? ia oa, ui a on?o aeiaaeeao ooai?th?oueny eeoa iaeei
ae?anoa?aiia?. I?e oeueiio a?aenooi?noue ni?i-ni?iiai? aca?iiae??
i?ioii?a a iieiaeaii? 5 ? 6 i??ei?aeeiiaiai oeeeeo na?ae/eoue, ui
cia/aiiy oi?n?iiiiai eooa I-N(6)-N(7)-I aeecueei aei 90i, ui oa?aeoa?ii
aeey niieoe c ae?aen?aeueiith i???ioaoe??th cai?niee?a a iieiaeaiiyo 5
oa 6.
Oe?eueiaa a?iiaoecaoe?y niieoee LX? i?e iaa??aaii? a eneeie? a
i?enooiino? ioeoiai? eeneioe aeicaieeea iaea?aeaoe ?i?aeacii??ei?aeei
LXV ? i?aeoaa?aeeoe oaeo aoi?eiiino? i?ioeano a?iiaoecaoe??.
"Aioene?aoiianueea" iai?aaeai?noue aca?iiae?? a aea/aieo ?aaeoe?yo aoea
i?aeoaa?aeaeaia ca aeiiiiiaith OO ? II? niaeo?ineii??.
3. Aca?iiae?y 3,4,5-o?eai?ii-1,2,4-o?eacieo c
2,3-aeea?ii-1,3-ae?a?eei?iiaiiiaie
3.1. Noaa?euei? nie?
1,2-ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?y
Oai?aoe/ii a?aeiiee oaeo ciaioaiiy ioeeaio?eueiino? aoii?a aoaeaoeth a
iieaeoeao acie?a i?e aaaaeai? aeiaeaoeiaeo aoii?a acioo, ia ciaeoia
naiai aeinoaoiueiai aenia?eiaioaeueiiai i?aeoaa?aeaeaiiy aeey ?aaeoe?e
ae?ai?iiacie?a c aiiiiaeie nenoaiaie. Oiio iaie aea/aia ?aaeoe?y
3,4,5-o?eai?ii-1,2,4-o?eacieo c a,b-aeea?iioaeeiiaie.
?aaeoe?y i?iaiaeeeanue a noaiaea?oieo oiiaao eei'yo?iiy neioii?a a
iaoaiie? c eaoae?oe/iith e?euee?noueth o?eaoeeai?io. I?iaeoeoaie
aeyaeeeny e?enoae?/i? niieoee aeiaoiai eie??o LXXXI-XC, ui iathoue
?ioaineaio ethi?ianoeaioe?th a iaoaiieueieo ?ic/eiao. A ?o ?* niaeo?ao
niinoa??aathoueny ?ioaineai? nioae i?e 1660 oa 1637 ni-1(noia?iiceoe?y
aaeaioieo eieeaaiue N=N, N=N ca'yce?a), a oaeiae o?e, ?iiae? /ioe?e
nioae a iaeano? 3200-3400 ni-1. A niaeo?ao II?, ie??i ioeueoeieaoo
a?iiaoe/ieo i?ioii?a, i?enooi? aeaa ?icoe?ai? neiaeaoe n o?i?/ieie
cnoaaie a iaeano? 6,0 i.ae oa 7,3 i.ae a?aeiia?aeii, ui cieeathoue i?e
aeiaeaaaii? aeaeoa?iiaoaiieo. Oaeei /eiii niaeo?aeuei? aeai?
i?aeoaa?aeothoue iayai?noue a neioaciaaieo niieoeao aeaio ai?iia?oi.
Aeaeo?iii? niaeo?e iiaeeiaiiy niieoe LXXXI-XC oa?aeoa?ecothoueny o?ueiia
?ioaineaieie nioaaie iiaeeiaiiy, iaea?eueo aeaeaea c yeeo eaaeeoue i?e
430-460 ii.
Inoaoi/ii no?oeoo?o niieoe LXXXI-XC aoei c'yniaaii ca aeiiiiiaith ?NA
ia i?eeeaae? niieoee LXXXV, yea aeyaeeanue
1,2-ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e a?ii?aeii,
nieueaaoiaaiei iaei??th iieaeoeith AeIOA.
Iaie cai?iiiiiaaia ianooiia noaia ooai?aiiy niieoe LXXXI-XC.
LXXII, LXXVI, LXXVIII R =H, LXXIII R = OCH3, LXXIV, LXXIX R = Cl, LXXV,
LXXX R = Br, XXVI R = NO2, XXVI, LXXII-LXXV R'= H, LXXVI R'= CH3,
LXXVII R'= OCH3, LXXVIII R'= NO2, LXXIX R'= Cl, LXXX R'= Br, LXXXI R =
R'= H, LXXXII R= OMe, R'=H; LXXXIII R= Cl, R'= H;.LXXXIV R= Br, R'= H;
LXXXV R= NO2, R'= H; LXXXVI R= H, R'= Me; LXXXVII R= H, R'= OMe;
LXXXVIII R= H, R'= NO2; LXXXIX R=R'= Cl; XC R=R'= Br.
Oaea iine?aeiai?noue noaae?e i?aeoaa?aeaeo?oueny oaeoii io?eiaiiy
ia?oei?aoo 1,2-ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?y a
?aaeoe?? a-a?iioaeeiio c 3,4,5-o?eai?ii-1,2,4-o?eacieii a i?enooiino?
oei?ii? eeneioe. A?eueo neeueia eeneioa nooo?ai i?enei?th? noaae?th
aeaa?ae?aoaoe??, ? ooai?aiiy a?aeiia?aeii? nie? niinoa??aa?oueny aaea
/a?ac 30 oaeeei i?ney ii/aoeo ?aaeoe??.
I?e ia?ae?enoae?caoe?? e?enoaeia?ae?ao?a niieoe LXXXI-XC c AeIOA
ooai?ththoueny nieueaaoe, ui i?noyoue iaeio iieaeoeo aeeiaoeeoi?iai?aeo.
I?ioean noi?iaiaeaeo?oueny nooo?aei a?inio?iiiei cnoaii aeiaaioaeeueiai?
nioae (Dl=60 ii) a aeaeo?iiieo niaeo?ao iiaeeiaiiy.
Oaeei /eiii, ia a?aei?io a?ae i?iaeoeo?a aca?iiae??
1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacieo c oaeeiiaeea?ii?aeaie,
3,4,5-o?eai?ii-1,2,4-o?eacie a aiaeia?/i?e ?aaeoe?? ooai?th? noaa?euei?
nie? o?eaciei[1,5-a]i??ei?ae?i?y c? caa?aaeaiiyi a?ae?aceiii?
ai?iia?oie. Oea iiaeia iiynieoe, ye ??ciith iine?aeiai?noth noaae?e
aca?iiae?? aeey aeacaieo ae?ai?i?a, oae ? nooo?aith paeao?oeeoi?noth
o?eacieueiiai oeeeeo, ui ni?ey? caa?aaeaiith N-ai?iia?oie.
3.2 O?i?/i? ia?aoai?aiiy nieae 1,2-ae?ai?ii-1,2,4-o?eaciei[1,5-a]-
i??ei?aeei?y
O?i?/i? aeanoeaino? nieae LXXXI-XC aea/ai? ia i?eeeaae? niieoe LXXXI,
LXXXV.
wmetafile8? ??XCII, XCIV, XCIV Ar = Ar' = Ph; XCIII, XCV, XCVII Ar=
4-NO2-C6H4, Ar'= Ph.
Oae, oe? niieoee aoeeeththoueny ioeoiaei aia?ae?eaeii a i??eaeei? ii
ai?iia?oi? a iieiaeaii? 2 a?oeeeeo, i?e oeueiio i?ioiaeeoue ae?i?ioaaiiy
N-ai?iia?oie. A ?aaeoe?? aeacaieo nieae c i-i?o?iaaicaeueaeaa?aeii
io?eiaii i?o?iaaic?e?aeaiiio?aei? XCIV, XCV. Eei'yo?iiy nieae
o?eacieii??ei?aeei?y LXXXI-LXXXV a oei?ioi?i? aai ni?iaa ?o
ae?aciooaaiiy aaaea aei ao?aoe N-ai?iia?oie ? ooai?aiiy iio?aeieo
aoaiicieii??ei?aeeia XCVI, XCVII. Ii?ii?iaiiy iaoaiieueiiai ?ic/eio nie?
LXXXI noi?iaiaeaeo?oueny aeano?oeoe??th i??ei?aeeiiaiai oeeeeo c
ooai?aiiyi 3,4ae?ai?ii-5-(N-aaici?e)-1,2,4-o?eacieo.
I?e aeei?enoaii? a ?aaeoe?? c o?eai?iii LXXI
1-a?ee-3-(4-i?o?ioai?e)-a,b-aeea?iii?iiaiii?a ii?yae c a?aeiia?aeieie
nieyie LXXXV, XCIX-CI ooai?ththoueny
1,2-ae?ai?ii-5-a?ee-7(4-i?o?ioai?e)-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e-6-
ieaoe N??-CV, aeo?ae yeeo c?inoa? i?e ca?eueoaii? /ano eei'yo?iiy
?aaeoe?eii? noi?o? aai aeei?enoaii? ye aeaeo?io?eueii? eiiiiiaioe
?aaeoe?? a-a?iioaeeii?a CVI, CVII.
XXVI, CVI Ar = Ph, XXIX, CVII Ar = C6H4Cl-p; XXX Ar = C6H4Br-p;
XXVII Ar = C6H4NO2-p, LXXXCV, CII Ar= Ph, XCIX, CIII
Ar= 4-Cl-C6H4; C, CIV R= 4-Br-C6H4; CI, CV Ar=
4-NO2-C6H6.
A ?* niaeo?ao niieoe N??-CV i?enooi? o?e nioae a iaeano? 3430-3100 ni-1
, ui na?ae/eoue i?i caa?aaeaiiy iaio ai?iia?oi, a oaeiae nioae i?e 1660
oa 1637 ni-1 (noia?iiceoe?y aaeaioieo eieeaaiue N=N, N=N ca'yce?a). A
niaeo?ao II?, ie??i ioeueoeieaoo a?iiaoe/ieo i?ioii?a, ? ?icoe?aiee
neiaeao N-ai?iia?oie a iaeano? 6 i.ae. ? neaai?icuaieaiee aeoaeao
N-ai?iia?oie a iaeano? a?eueo neaaeeo iie?a (7,5 i.ae.). No?oeoo?a
niieoe N??-CV inoaoi/ii anoaiiaeaia ca aeiiiiiaith iaoiaeo ?NAe aeey
ieaoa N??.
Aoaeiao niieoe N??-CV iiaeii cia?aceoe iaa??ii ?aciiainieo no?oeoo?
A-A
wmetafile8? ??RX??????????????X????i–???uCy???????o
aiae?c aeicaiey? c?iaeoe aeniiaie, ui iniiaiee aianie iaeaaeeoue
no?oeoo?ai N-D. Ia ei?enoue inoaii?o na?ae/eoue aeiaaeeia ca'yceo N=I
(ca?aeii aeaieo ?NA aeey niieoee N??) oa ?nioaaiiy i??ei?aeeiiaiai
oeeeeo a eiioi?iaoe?? neeueii nieiuaii? aaiie.
4. ?aaeoe?? 1,5-ae?ai?iioao?acieo c 1,3-ae?a?eei?iiaiiiaie
Iaie iieacaii, ui i?iaaaeaiiy ?aaeoe?? 1,5-ae?ai?iioao?acieo c
oaeeiiaie (eei'yo?iiyi a AeIOA ia i?ioyc? o?ueio aiaeei) i?ecaaei aei
oi?ioaaiiy
1-(5-oao?acie?e)-3,5-ae?a?ee-4,5-aeea?ae?i-2-i??acie?i?a CXIV-CXXI, a ia
oao?acieio?eacai?iiaeo nenoai, ye aaaaeaeiny ?ai?oa.
wmetafile8? ??D?? ????????????f?1/4????
w§???uEy??????1/4????Times New
Roman??c???-?????.????"I??????
???u?????yyy?"????-????ue???????????-????$???????"I$E
$???
???u??????????"????-????ue??yyy??????-????1/2?™???
????-????-????$?—3/4??1/4?1/2!?!—3/4????-????-?
???”?!???”?????-????-????$?!—?!’?„’?„—?!—????-?
???-????ae??????y????-????-????$?c?a?u??????c?
???-????-????3/4????o????-????-????$?o?o?
3/4?3/4?o?
???-????-????g5???8/????-????-????$?8e5io?:
o?68e???-????-????hq???%E???-????-????$?rj
ofE#I#I'rj???-????-????/S????S???-????-
????$?VoQoQ?V?Vo???-????-????A=???$I???-
????-????$???=DI'I$?"?????-????-????–???
Ue?2???-????-????$?——1TH?3U?—???-????-????
‘ ??? ???-????-????$?F’?’?FF’???-????-
????‘????????-????-????$?‘’?’?‘‘’???-
????-????ss?o???—???-????-????$?oY?/a?——
oY????-????-????e?‰???N?2???-????-????$??c??i?
2O?2I??c????-????-????;(???N????-????-????$?
N?
N?+;)=&=N????-????-????Oe?o???9???-????-?
???$?o*?oO?::o*????-????-?????|????ss???-?
???-????$?|°?|«?a«?a°?|°????-????-????
????O?Y???-????-????$?B=WN?O?B???-????-?
???*?j???#P???-????-????$?S%N#h*?m*?S%???-?
???-????? Neioaciaai? niieoee aoee ?aeaioeo?eiaai? ca aeiiiiiaith
?* ? II? niaeo?ineii??. Oae, a ?* niaeo?ao, ciyoeo a oaaeaoeao KBr,
a?aenooiy iieina i?e 2200 ni-1, ui na?ae/eoue i?i ?nioaaiiy niieoe
CXIV-CXXI a oao?acieuei?e, a ia aceaei?e oi?i?. Nioaa i?e 1630 ni-1
a?aeianaia aei noia?iiceoe?? eieeaaiue N=N oa C=N ca'yce?a, a oe?iea
nioaa i?e 3400 ni-1 iaeaaeeoue eieeaaiiyi anioe?eiaaii? ai?iia?oie. A
niaeo?ao II? niieoe CXIV-CXXI, ciyoeo a AeINI-D6, niinoa??aa?oueny
ioeueoeieao i?ioii?a aeaio a?iiaoe/ieo yaea?, AAO-nenoaia i??acie?iiaiai
o?aaiaioa iieaeoee oa ?icoe?aiee neiaeao iaeiiai i?ioiia a iaeano? 16
i.ae. Inoaoi/ii no?oeoo?a niieoe CXIV-CXXI aoea anoaiiaeaia ca
aeiiiiiaith iaoiaeo ?NA ia i?eeeaae? niieoee CXIX. Iaeiioeii?noue
niaeo?aeueieo aeaieo i?iaeoeoa NO?O oa an?o ?io?o niieoe oeueiai ?yaeo
iieacaea, ui i?iaeoeoaie ?aaeoe?? 1,5-ae?ai?iioao?acieo c oaeeiiaie ?
1-(5-oao?acie?e)-3,5-ae?a?ee-4,5-aeea?ae?i-2-i??acie?ie CXIV-CXXI.
A?aeiii, ui e?eueoeaai-eaioethaiaa oaooiia??y ? cae/aeiei yaeuai aeey
1,5aeecai?uaieo oao?acie?a, a i?e iaa??aaii? 1,5-ae?ai?iioao?acie?a
i?ioiaeeoue ia?aa?oioaaiiy Ae?i?ioa. A iao?e ?aaeoe??, i?iaeoeoii oaeiai
ia?aa?oioaaiiy ? 5a?ae?aceii-1I-oao?acie, yeee a iiaeaeueoiio ? anooia?
a ?aaeoe?th c oaeeiiaie ooai?thth/e niieoee CXIV-CXXI. Iaio
a??ia?aeiith, ia iao iiaeyae, ? o/anoue a ?aaeoe?? c oaeeiiaie aceaeii?
oi?ie 1,5-ae?ai?iioao?acieo.
aeniiaee
1. Anoaiiaeaii, ui 4-a?ee-1,2-ae?ai?ii?i?aeaciee a ?aaeoe?yo c
a,b-iaiane/aieie eaoiiaie, ?o a,b-aeea?iiiio?aeieie ? b-aeeeaoiiaie
iiaiae?oue naaa, ye oeiia? 1,3aeeioeeaio?ee, ooai?thth/e aeea?ae?i- aai
aaoa?ia?iiaoe/i? iio?aei?
7-ai?ii-2,4,5-o?ea?ee?i?aeaci[1,2-b]i??eae?c?io.
2. Iieacaii, ui ?aaeoe?y 4,5-aeeoai?e-1,2-ae?ai?ii?i?aeacieo c
oaeeiiaie oa a,baeea?iioaeeiiaie noi?iaiaeaeo?oueny ae?i?ioaaiiyi
N-ai?iia?oie oa ooai?aiiyi
6-iene-2,3-aeeoai?e-5,6-aeea?ae?i-5,7-ae?a?ee?i?aeaci[1,2-a]i??ei?aeei?a
(6-iene-2,3-aeeoai?e-5,7-ae?a?ee?i?aeaci[1,2-a]i??ei?aeei?a) oa
2,3-aeeoai?e-5,7-ae?a?ee?i?aeaci[1,2-a]i??ei?aeei?a a?aeiia?aeii.
Anoaiiaeaii,ui i?ioean ieeneaiiy aeea?ae?ino?oeoo?e ia?aaeo? noaae??
aeea?ae?oaaiiy.
3. Aea/aii o?i?/io iiaaae?ieo 3,4,5-o?eai?ii-1,2,4-o?eacieo a ?aaeoe?yo
c a,baeea?iioaeeiiaie oa aia?oa iieacaii, ui i?iaeoeoaie ?aaeoe?? ?
noaa?euei? nie?
1,2-ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?y,
cai?iiiiiaaii iinoaae?eio noaio ?o ooai?aiiy.
4. Aeiaaaeaii, ui i?ioean oi?ioaaiiy iio?aeieo
?i?aeaci[1,5-b]i??eaeac?io, ?i?aeaci[1,2-a]i??ei?aeeio, nieae
o?eaciei[1,5-a]i??ei?aeei?y i o?eaciei[1,5-a]-i??ei?aeei?e ieao?a
ia?aa?aa? /a?ac noaae?th b-aaoa?eethaaiiy c ianooiiith
oeeeeieiiaeainaoe??th, i?e oeueiio ?aae?co?oueny "aioene?aoiianueea"
iiaeaeue aca?iiae??.
5. Anoaiiaeaii, ui a aeiaaeeo
3-(i-i?o?ioai?e)-1-a?ee-2,3-aeea?iii?iiaiii?a, ii?yae c nieyie
1,2-ae?ai?ii-5-(i-i?o?ioai?e)-7-a?ee-1,2,4-o?eaciei[1,5-a]-
i??ei?aeei?y, ooai?ththoueny iaci?iii? no?oeoo?e -
1,2-ae?ai?ii-5-(i-i?o?ioai?e)-7-a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e-6
-ieaoe, aeo?ae yeeo c?inoa? ?c c?inoaiiyi /ano ia?aa?ao ?aaeoe??.
6. Aea/aii o?i?/i? aeanoeaino? noaa?eueieo nieae
1,2-ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?y, aeiaaaeaii,
ui ?aaeoe?? eaeooue ye ii a?ae?aceii?e, oae ? ii a?iiaoe/i?e ai?iia?oi?,
aeyaeaii i?ioeane oioiaeano?oeoe?? aeayeeo i?aaenoaaiee?a ?yaeo.
7. Iieacaii, ui 1,5-ae?ai?iioao?acie a ?aaeoe?? c oaeeiiaie cacia?
ia?aa?oioaaiiy Ae?i?ioa c ooai?aiiyi
1-(5-oao?acie?e)-3,5-ae?a?ee-4,5-aeea?ae?i-2-i??acie?i?a, a ia
5,7-ae?a?ee-5,6-aeea?ae?i-4I-oao?aciei[1,5-b]-1,2,4-o?eacai?i?a, ye
aaaaeaeiny ?ai?oa.
Iniiai? ?acoeueoaoe aeena?oaoe?? iioae?eiaaii a ?iaioao:
1. Eiein I.I., I?eia A.Ae., Iaiiiia A.A., Aaoia? A.I. Neioac
2-aieii-4,5,7-o?ea?eeeieaeaci[1,5-b]ie?eaeaceiia. // Oeiey aaoa?ioeeee.
niaae. - 1998.- ?10. -n. 1397-1403.
2. Eiein I.I., I?eia A.Ae., Iaiiiia A.A. Aaoia? A.I., Oeoeei I.A.,
Eaaoieoeeay I.A. Coaaeeueiua niee 1,2,4-o?eaciei[1,5-a]ie?eieaeeiey. //
Oeiey aaoa?ioeeee. niaae. - 1999.- ?6.- c. 796-804.
3. Eiein I.I., I?eia A.Ae., Iaiiiia A.A., Oeoeei I.A. Neioac
aeeaeae?ii?iecaiaeiuo 7-aieii-2,4,5-o?ea?eeeieaeaci[1,5-b]ie?eaeaceia.
// Oeiey aaoa?ioeeee. niaae.- 1999.- ?10.- C..1338-1346
4. ?aaeoe?? aaoa?ioeeee?caoe?? ia iniia? 1,2ae?ai?ii-4-a?ee?i?aeacie?a.
Eiein I.I., I?eia A.Ae., Iaiiiia A.A. // Iaoa??aee Anaoe?a?inueei?
eiioa?aioe?? "O?i?y acioai?nieo aaoa?ioeeee?a." Oa?e?a 1997.- n. 26.
5. Novel ways of synthesis and transformation of
dihydroazolopyrimidines and analogues. Orlov V.D., Desenko S.M., Kolos
N.N., Lipson V.V., Shiskin O.V., Paponov. B.V., Chebanov V.A. // XVI
Mendeleev Congres on General and Applying Chemistry. Moscow.- 1988.-
p.196-197.
6. Iao?ea?aeueia ?aaeoe?y 1,5-ae?ai?iioao?acieo c a,b-iaiane/aieie
eaoiiaie. Eiein I.I., I?eia A.Ae., Iaiiiia A.A., Oeoe?i I.A. //
Iaoa??aee XVIII Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i??.
Aei?i?iiao?ianuee.- 1988.- n. 163.
7. ?aaeoeee oeeeeieiiaeainaoeee n o/anoeai aaoa?ioeeeee/aneeo
i-aeeaieiia, a,biai?aaeaeueiuo ea?aiieeueiuo niaaeeiaiee e eo
i?iecaiaeiuo. Eiein I.I., Iaiiiia A.A., *aaaiia A.A., Oeuaiei A.A.,
I?eia A.Ae., Aa??ceeia O.A. // Iaoa?eaeu iaaeaeoia?iaeiie iao/iie
eiioa?aioeee "I?aaie/aneee neioac e eiiaeiaoi?iay oeiey." Iineaa. 1999.-
n. 125.
8. Iaiiiia A.A., Eiein I.I., I?eia A.Ae. Acaeiiaeaenoaea
i-aeeaieiiacieia niaea?aeaueo aeae?aceiioth aieiia?oiio n
a,b-iaianuuaiuie eaoiiaie e eo i?iecaiaeiuie. // ?aaeiiaeueiay
eiioa?aioeey iieiaeuo o/?iuo e nooaeaioia ii aeooaeueiui aii?inai oeiee.
Aeiai?iiao?iane.- 1999.- n. 19.
AIioaoe?y
Iaiiiia A.A. Eiiaeainiaai? aaoa?ioeeeee - i?iaeoeoe aca?iiae??
ae?ai?iiacie?a c a,b-iaiane/aieie eaoiiaie. - ?oeiien
Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe ca
niaoe?aeuei?noth 02.00.03 - i?aai?/ia o?i?y. Oa?e?anueeee iaoe?iiaeueiee
oi?aa?neoao ?i. A.I.Ea?ac?ia, Oa?e?a, 1999.
Aeine?aeaeaii ?aaeoe?? aeayeeo ae?ai?iiacie?a, ui i?noyoue N-ai?iia?oio
c a,biaiane/aieie eaoiiaie oa ?o iio?aeieie. Anoaiiaeaii, ui
1,2-ae?ai?ii-4-a?ee?i?aeaciee, 1,2-ae?ai?ii-4,5-aeeoai?e?i?aeacie,
3,4,5-o?eai?ii-1,2,4-o?eacie a ?aaeoe?yo c oaeeiiaie oa ?o
a,b-aeea?iiiio?aeieie aenooiathoue oeiiaeie 1,3aeeioeeaio?eaie.
Iaea?aeaii iia? iaiane/ai? ? aaoa?ia?iiaoe/i? iio?aei?
7ai?ii-2,4,5-o?ea?ee?i?aeaci[1,5-b]i??eaeacei?a,
2,3-aeeoai?e-5,7-ae?a?ee-6-iene-?i?aeaci[1,2-a]i??ei?aeei?a,
2,3-aeeoai?e-5,7-ae?a?ee?i?aeaci[1,2-a]i??ei?aeei?a,
1,2ae?ai?ii-5,7-ae?a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e a?ii?ae?a ?
1,2-ae?ai?ii-(i-i?o?ioai?e)-7-a?ee-1,2,4-o?eaciei[1,5-a]i??ei?aeei?e-6-i
eao?a. Iieacaii, ui aeey 1,5-ae?ai?iioao?acieo a ?aaeoe?? ?c
1,3-ae?a?eei?iiaiiiaie niinoa??aa?oueny ia?aa?oioaaiiy Ae?i?ioa c
ooai?aiiyi a?aeiia?aeieo
1-(5-oao?acie?e)-3,5-ae?a?eei??acie?i?a.
Cae?eniaii o?i?/io iiae?o?eaoe?th neioaciaaieo niieoe. Aea/aii ?o
o?ceei-o?i?/i? aeanoeaino?. Io?eiai? niieoee ?aeaioeo?eiaaii ca
aeiiiiiaith niaeo?aeueieo iaoiae?a, a aeey ie?aieo i?aaenoaaiee?a
a?eueoino? ?yae?a neioaciaaieo niieoe no?oeoo?a aoea inoaoi/ii
anoaiiaeaia ca aeiiiiiaith ?NA.
Eeth/ia? neiaa: ae?ai?iiaciee, oaeeii, oeeeeecaoe?y, ?i?aeacii??eaeacei,
acieii??ei?aeei, noaa?euei? nie?, ieao, niaeo?aeuei? iaoiaee.
AIIOAOeEss
Iaiiiia A.A. Eiiaeaine?iaaiiua aaoa?ioeeeeu - i?iaeoeou acaeiiaeaenoaey
aeeaieiiacieia n a,b-iaianuuaiiuie eaoiiaie. - ?oeiienue.
Aeena?oaoeey - ia i?aaao ?oeiiene - ia nieneaiea o/?iie noaiaie
eaiaeeaeaoa oeie/aneeo iaoe ii niaoeeaeueiinoe 02.00.03 - i?aaie/aneay
oeiey. - Oa?ueeianeee iaoeeiiaeueiue oieaa?neoao ei A.I. Ea?aceia,
Oa?ueeia, 1999.
Enneaaeiaaia ?aaeoeey iaeioi?uo aeeaieiiacieia, niaea?aeaueo
aeae?aceiioth aieiia?oiio n a,b-iaianuuaiiuie ea?aiieeueiuie
niaaeeiaieyie e eo i?iecaiaeiuie. Onoaiiaeaii, /oi
1,2-aeeaieii-4-a?eeeieaeacie a ?aaeoeee n 1,3aeecaiau?iiuie i?iiaiiiaie
ia?acoao 2,4-aeecaiau?iiua
7-aieii-5-a?ee-3,4-aeeaeae?ieieaeaci[1,5-b]ie?eaeaceiu, a a neo/aa
a,b-aeea?iii?iecaiaeiuo yoeo eaoiiia eee eo aoeaoeeaiiauo aiaeiaia -
2,4-aeecaiau?iiua 7-aieii-5-a?ee-eieaeaci[1,5-b]ie?eaeaceiu.
1,2-Aeeaieii-4,5-aeeoaieeeieaeacie a ?aaeoeee n 1,3-aeea?eei?iiaiiiaie
(oaeeiiaie) a caaeneiinoe io oneiaee i?iaaaeaiey ?aaeoeee ia?acoao eeai
3,4aeeoaiee-5,7-aeea?ee-6-ieneeieaeaci[1,5-a]ie?eieaeeiu eeai eo
7,8aeeaeae?ii?iecaiaeiua. I?e eniieueciaaiee a,b-aeea?iicaiau?iiuo
1-a?ee-3- (4-ieo?ioaiee)-i?iiaiiiia ia?acothony i?iecaiaeiua
3,4-aeeoaiee-5-
(4-ieo?ioaiee)-7-a?eeeieaeaci[1,5-a]ie?eieaeeia.
?ac?aaioai iaoiae neioaca noaaeeueiuo nieae
2,3-aeeaieii-5,7-aeea?ee-1,2,4-o?eaciei[1,5-a]ie?eieaeeiey ?aaeoeeae
3,4,5-o?eaieii-1,2,4-o?eaciea n a,baeea?iii?iecaiaeiuie oaeeiiia e
a-a?iioaeeiiaie. Onoaiiaeaii, /oi i?e eniieueciaaiee a ?aaeoeee
1-a?ee-3-(4-ieo?ioaiee)-i?iiaiiiia ia?yaeo n nieyie
2,3-aeeaieii-5,7-aeea?ee-1,2,4-o?eaciei[1,5-a]ie?eieaeeiey ia?acothony
iacieiiiua
2,3-aeeaieii-5-a?ee-7-(4-?eo?ioaiee)-1,2,4-o?eaciei[1,5-a]ie?eieaeeiee-6
-ieaou.
Ana enneaaeiaaiiua aeeaieiiacieu niaea?aeao o?e e aieaa iioaioeeaeueiuo
?aaeoeeiiiuo oeaio?a, a oii /enea aieiia?oiiu i?e aeoeeiaeueiuo aoiiao
acieueiiai oeeeea. Yoi i?aaeiieaaaao aicueuaeiinoue oi?ie?iaaiey a
?aaeoeeyo n a,b-iaianuuaiuie eaoiiaie e eo i?iecaiaeiuie oanoe e
naie/eaiiuo aaoa?ioeeeeia. Ia?aua ia?acothony i?e o/anoee a ?aaeoeee
yiaeioeeeee/aneiai N- eeai N-aoiia aciea e iaeiie ec aai aieiia?oii.
Aoi?ua - i?e o/anoee a ?aaeoeee iaaeo yeciaieiia?oii aeeaieiiaciea. Iaie
onoaiiaeaii, /oi 1,2-aeeaieii-4-a?ieeieaeacieu,
1,2-aeeaieii-4,5-aeeoaieeeieaeacie e 3,4,5-o?eaieii-1,2,4-o?eacie a
?aaeoeeyo n a,b-iaianuuaiuie eaoiiaie e eo i?iecaiaeiuie aunooiatho eae
oeie/iua 1,3-aeeioeeaioeeu e ia?acotho auoaiienaiua aeoeeeee/aneea
acieiaceiiaua e acieiaceieaaua nenoaiu.
No?oeoo?a aieueoeinoaa iieo/aiiuo niaaeeiaiee iicaieyao inouanoaeoue eo
oeie/aneoth iiaeeoeeaoeeth. A neeo yoiai enneaaeiaaiu iaeioi?ua
oeceei-oeie/aneea naienoaa neioace?iaaiiuo niaaeeiaiee. Iieacaia
ia?niaeoeaiinoue aeaeueiaeoaai eco/aiey eo ?aaeoeeiiiuo aiciiaeiinoae.
A ?aaeoeeyo 1,5-aeeaieiioao?aciea n 1,3-aeea?eei?iiaiiiaie neioace?iaaiu
i?iecaiaeiua 5-(3,5-aeeoaiee-4,5-aeeaeae?i-1-ie?acieee)-1I-oao?aciea. A
aeaiiii neo/aa ?aaeoeey nii?iaiaeaeaaony ?ane?uoeai oao?acieueiiai
oeeeea n iineaaeothuae ?aoeeeeecaoeeae a niioaaonoaothuea
5-(3,5-aeeoaiee-4,5-aeeaeae?i-1-ie?acieee)-1I-oao?acieu.
Iieo/aiiua niaaeeiaiey eaeaioeoeoee?iaaiu iaoiaeaie EE OO e II?
niaeo?ineiiee. Aeey anao aia?aua iieo/aiiuo niaaeeiaiee auiieiai
yeaiaioiue aiaeec ia acio. Aeey eeth/aauo niaaeeiaiee no?oeoo?a
ieii/aoaeueii onoaiiaeaia i?e iiiiue ?aioaaiino?oeoo?iiai aiaeeca.
Eeth/aaua neiaa: i-aeeaieiiacie, oaeeii, oeeeeecaoeey,
eieaeaciie?eaeacei, acieiie?eieaeei, neaaeeueiua niee, ieao,
niaeo?aeueiua iaoiaeu.
SUMMARY
Paponov B.V. The Condensed Heterocycles - products of reactions of
Diaminoazoles with a,b-Unsaturated Kethones. -manuscript.
Thesis for a candidate degree of science in chemistry by speciality
02.00.03 –organic chemistry, Kharkov National University, Kharkov 1999.
The reaction of some diaminoazoles, containes N-aminogroup with
a,bunsaturated carbonyl compounds and its derivatives has been
descripted in this paper. New unsaturated and heteroaromatic azoloazinic
and mesomeric systems have been synthesed. The synthetic modification of
obtained compounds have been carried out. Some of the properties of
these compounds have been investigated in the paper. Every synthesed
compounds have been identified by spectral methods. The structure of the
most of the series of obtained compounds has been finally established by
X-ray.
Key words: ortho-diaminoazole, chalcone, cyclization,
imidazopyridazine, azolopyrimidine, stable salt, olate, spectral method.
Нашли опечатку? Выделите и нажмите CTRL+Enter
