Синтез, фізико-хімічні та біологічні властивості N- і S-заміщених моно- і біциклічних азагетероциклів: Автореф. дис… канд. фармац. наук / І.М. Шевче

I?I?NOA?NOAI IOI?IIE CAeI?IA’ss OE?A?IECAII??CUeEEE AeA?AEAAIEE
IAAeE*IEE OI?AA?NEOAO

Ia i?aaao ?oeiieno

OAA*AIEI ?IIA IEEIEA?AIA

OAeE 615.276+615.214.2.547.791.547.831.1.547.792.1

Neioac, o?ceei-o?i?/i? oa a?ieia?/i?

aeanoeaino? N- ? S-cai?uaieo iiii-

? a?oeeee?/ieo acaaaoa?ioeeee?a

15.00.02 – oa?iaoeaaoe/ia o?i?y ? oa?iaeiaiic?y

Aaoi?aoa?ao

aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiyeaiaeeaeaoa oa?iaoeaaoe/ieo
iaoe

Caii??aeaey — 1999

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia ia eaoaae?? oa?iaeiaiic??

Caii??cueeiai aea?aeaaiiai iaaee/iiai oi?aa?neoaoo

Iaoeiaee ea??aiee: aeieoi? oa?iaoeaaoe/ieo iaoe, i?ioani?

Aeiey A?eoi? Naiaiiae/, Caii??cueeee aea?aeaaiee

iaaee/iee oi?aa?neoao, caa?aeoaa/ eaoaae?e

oa?iaeiaiic??.

Io?oe?ei? iiiiaioe: aeieoi? oa?iaoeaaoe/ieo iaoe,

i?ioani? Neiye ?a?na Noaiai?aia,

Caii??cueeee aea?aeaaiee iaaee/iee oi?aa?neoao,

i?ioani? eaoaae?e oa?iaoeaaoe/ii? o?i??;

aeieoi? oa?iaoeaaoe/ieo iaoe,

i?ioani? Iaothi?i Aaiaae?e Iaaeiae/,

Oa?e?anueea iaaee/ia aeaaeai?y

i?neyaeeieiiii? ina?oe,

caa?aeoaa/ eaoaae?e ee?i?/ii? a?io?i??

? noaeiai-iaaee/ii? oieneeieia??.

I?ia?aeia onoaiiaa: Oe?a?inueea oa?iaoeaaoe/ia aeaaeai?y (i. Oa?e?a)

Caoeno a?aeaoaeaoueny » 15 » aeiaoiy 1999 ?. i 13 aiaeei? ia can?aeaii?
a/aii? ?aaee E 17.600.01 o Caii??cueeiio aea?aeaaiiio iaaee/iiio
oi?aa?neoao? ca aae?anith: 330035, i. Caii??aeaey, i?ini. Iayeianueeiai,
26.

C aeena?oaoe??th iiaeia iciaeiieoenue a iaoeia?e a?ae?ioaoe?
oi?aa?neoaoo (330035, i. Caii??aeaey, i?ini. Iayeianueeiai, 26).

Aaoi?aoa?ao ?ic?neaii » 9 » aa?aniy 1999 ?.

A/aiee nae?aoa?

niaoe?ae?ciaaii? a/aii? ?aaee E 17.600.01

aeioeaio No??eaoeue E.I.

Caaaeueia oa?aeoa?enoeea ?iaioe

Iio?aei? 1,2,4-o?eacieo yaeythoueny iniiaith aeey noai?aiiy
aenieiaoaeoeaieo e?ea?nueeeo cania?a. Cai?uai? 1,2,4-o?eacieo
canoiniaothoueny ye aenieiaoaeoeai? i?ioei?e?iai? oa aiaeaioe/i?
e?ea?nuee? caniae (aciiai).

Ca inoaii? ?iee ia Oe?a?i? noai?aii iiaee i?ea?iaeueiee i?aia?ao,
o?io?eacie?i, yeee ? iio?aeiei 1,2,4-o?eacieo ? canoiniao?oueny ye
aaiaoii?ioaeoi?iee, aioeieneaeaioiee ? ?aiicaaith/ee can?a. Na?aae
iio?aeieo 5-o?i-1,2,4-o?eacie?a ciaeaeai? oaeiae niieoee, ye?
aeyaeythoue aenieo i?ioei?e?iaio, i?ioea?eaeiao, aiaeueaacoth/o,
i?ioecaiaeueio, ae?o?aoe/io oa ?io? aeaee aeoeaiino?.

Aeine?aeaeaiiy a?o/eciyieo oa ca?oa?aeieo a/aieo (Eieo ?.A., Iaco? ?.A.,
Oeo?eai I.I., Aeiaio I. oa ?io?) na?ae/aoue i?i oa, ui iio?aei?
1,2,4-o?eacieo ia?niaeoeaiee eean a?ieia?/ii aeoeaieo niieoe.
Caoe?eaaeai?noue aei aeeaoiai aea/aiiy o?i?/ieo, o?ceei-o?i?/ieo oa
a?ieia?/ieo aeanoeainoae 5-o?i-1,2,4-o?eacie?a oa ?o iio?aeieo ae?inea a
inoaii?e /an o ca’yceo c oei, ui 3-iiii- oa 3,4-aeecai?uai?
5-o?i-1,2,4-o?eacie?a aeinooii? aeey neioaco, ?aaeoe?eii-caeaoi? ?
aeineoue ia?niaeoeai? aeey neioaco a?ieia?/ii aeoeaieo niieoe.

Aeooaeuei?noue oaie. Iacaaaeath/e ia iayai?noue ioae?eaoe?e ii ?ic?iaoe?
iaoiae?a neioaco, aea/aiith o?i?/ieo oa a?ieia?/ieo aeanoeainoae
1,2,4-o?eacie?i-5-o?ii?a, aaaaoi ieoaiue ?o aoaeiae, o?ceei-o?i?/ieo oa
oa?iaeieia?/ieo aeanoeainoae aea/ai? iaaeinoaoiuei.

O ca’yceo c oeei, aea/aiiy o?i??, ?aaeoe?eii? ni?iiiaeiino? oa
caeaaeiino? a?ieia?/ii? aeoeaiino? a?ae aoaeiae iiaeo iio?aeieo
5-o?i-1,2,4-o?eacie?a ? aeooaeueiei, ia? oai?aoe/io oa i?aeoe/io
cia/ei?noue ? iio?aao? iiaeaeueoiai aea/aiiy.

Ca’ycie ?iaioe c iaoeiaeie i?ia?aiaie, ieaiaie, oaiaie. ?iaioa aeeiiaia
o a?aeiia?aeiino? c ieaiaie i?iaeaie “Oa?iaoe?y” IIC Oe?a?ie oa
iaoeiai-aeine?aeii? ?iaioe Caii??cueeiai aea?aeaaiiai iaaee/iiai
oi?aa?neoaoo (? aea?aeaaii? ?a?no?aoe?? 196U13916, oeo? oaie 1I
15000596).

Iaoa ? caaea/? aeine?aeaeaiiy. Iniiaiith iaoith ?iaioe ? iiooe niieoe c
i?ioei?e?iaiith, i?ioea?eaeiaith, aeai?eioth/ith, ae?o?aoe/iith,
aiaeueaacoth/ith, aiaeaioe/iith oa aioea?eoi?/iith aeoeai?noth na?aae
iio?aeieo 5-o?i-1,2,4-o?eacie?a, a oaeiae anoaiiaeaiiy caeiiii??iinoae
i?ae o?i?/iith aoaeiaith ? a?ieia?/iith ae??th.

Aeey ?aae?caoe?? caieaiiaaii? iaoe iaiao?aeii aoei ae??oeoe ianooii?
caaaeaiiy:

— aeine?aeeoe ?aaeoe?? iio?aeieo 1,2,4-o?eacie?i-5-o?ii?a c ai?iaie,
aaeiaaiaeeaiaie, aeeaaeiaaiaeeaiaie, a-aaeiaaieeneioaie, ?o ao??aie, oa
aaeiaaiaaoa?ioeeeeaie. ?ic?iaeoe i?aia?aoeai? iaoiaee neioaco
5-aee?eo?i-, 5-aaoa?eeo?i-, 5-ea?aieneaee?eo?i-,
5-aeeieneea?aii?eiaoeeo?i-, 5-a?ae?aceiiea?aii?eiaoeeo?i-1,2,4-o?eacie?a
? iio?aeieo 1,2,4-o?eaciei(3,4-a)-o?acie?a;

— aeine?aeeoe ?aaeoe?eio caeaoi?noue 1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo
eeneio, ?o ao???a ? a?ae?aceae?a;

— ia iniia? eaaioiai-o?i?/ieo ?ic?aooie?a ni?iaiicoaaoe iai?aaeaiiy
?aaeoe?? aee?ethaaiiy 1,2,4-o?eacie?i-5-o?ii?a;

— cae?enieoe a?ieia?/iee ne?ei?ia neioaciaaieo niieoe ? a?ae?a?aoe
iaea?eueo ia?niaeoeai? a?ieia?/ii aeoeai? ?a/iaeie aeey aeiee?i?/ieo
aeine?aeaeaiue.

Iaoeiaa iiaecia iaea?aeaieo ?acoeueoao?a. Ia iniia? aeaieo
eaaioiai-o?i?/ieo ?ic?aooie?a ca iaoiaeaie Ia??ca?a-Ia??a-Iiiea,
ni?iaiiciaaia iai?aaeai?noue ?aaeoe?? aee?ethaaiiy
1,2,4-o?eacie?i-5-o?ii?a. I?iaaaeaii oe?eani?yiiaaiee neioac a?ieia?/ii
aeoeaieo niieoe na?aae 3-iiii- ? 3,4-aeecai?uaieo
1,2,4-o?eacie?i-5-o?ii?a. Iaoiaeaie OO-, ?*-niaeo?ineii??,
ian-niaeo?iiao??? oa oiieioa?iai? o?iiaoia?ao?? aea/ai? o?ceei-o?i?/i?
aeanoeaino? neioaciaaieo niieoe. ?ic?iaeai? i?aia?aoeai? iaoiaee neioaco
aeayeeo 5-aee?eo?i-, 5-ea?aieneaee?eo?i-, 5-aaoa?eeo?i-1,2,4-o?eacie?a,
nieae 1,2,4-o?eacie?i-5-o?ii?a c ai?iaie ? iio?aeieo
1,2,4-o?eaciei(3,4-a)-o?acie?a.

Aea/aia a?ieia?/ia aeoeai?noue ia?ae?/aieo aeua iio?aeieo, anoaiiaeai?
aeaye? caeiiii??iino? aca?iica’yceo a?ieia?/ii? ae?? oa o?i?/ii?
aoaeiae.

I?aeoe/ia cia/aiiy iaea?aeaieo ?acoeueoao?a. Cai?iiiiiaaiee a ?iaio?
aenia?eiaioaeueii-oai?aoe/iee iaoa??ae na?ae/eoue i?i ia?niaeoeai?noue
iiooeo a?ieia?/ii-aeoeaieo ?a/iaei na?aae 3-iiii-, 3,4-aeecai?uaieo
1,2,4-o?eacie?i-5-o?ii?a, iio?aeieo 1,2,4-o?eaciei(3,4-a)-o?acie?a.

?acoeueoaoe o?i?/ieo aeine?aeaeaiue ii neioaco iio?aeieo 5-o?i-,
5-aee?eo?i-, 5-ea?aieneaee?eo?i-1,2,4-o?eacie?a aeei?enoiaothoueny i?e
i?iaaaeaii? iaoeiai-aeine?aeieo ?ia?o ia eaoaae?ao i?aai?/ii? ?
iai?aai?/ii? o?i??, oa?iaeieia??, a?noieia??, i?e?ia?ieia?? ?
a??onieia?? Caii??cueeiai aea?aeaaiiai iaaee/iiai oi?aa?neoaoo, ia
eaoaae?ao oa?iaeioa?ai?? ? oa?iaeieia?? Oe?a?inueei? oa?iaoeaaoe/ii?
aeaaeai??.

Aeey aeiee?i?/iiai aea/aiiy ?aeiiaiaeiaaia eae??aa n?eue
3-(4-i??eaeee)-1,2,4-o?eacie?e-5-ia?eaioiioeoiai? eeneioe, yea ia?
aenieo aioea?eoi?/io aeoeai?noue.

Iniaenoee aianie caeiaoaa/a. Neioaciaaii 94 niieoee, c yeeo 80 aia?oa,
aea/aia ?o ?aaeoe?eia caeaoi?noue ? o?ceei-o?i?/i? aeanoeaino?.
Anoaiiaeai? oa ?ioa?i?aoiaai? eaaioiai-o?i?/i? ?ic?aooiee, niaeo?aeuei?
oa?aeoa?enoeee neioaciaaieo niieoe. ?acoeueoaoe a?ieia?/ieo
aeine?aeaeaiue aeaee ciiao anoaiiaeoe ie?ai? aeaiaioe ca’yceo i?ae
o?i?/iith aoaeiaith oa oa?iaeieia?/iith ae??th. Aeey aeiee?i?/iiai
aeine?aeaeaiiy c iaoith noai?aiiy ia eiai iniia? iiaiai e?ea?nueeiai
caniao ?aeiiaiaeo?oueny eae??aa n?eue
3-(4-i??eaeee)-1,2,4-o?eacie?e-5-ia?eaioiioeoiai? eeneioe, yea ia?
aenieo aioea?eoi?/io aeoeai?noue ? iecueeo oiene/i?noue.

Ai?iaaoe?y aeena?oaoe??. Iaoa??aee ?iaioe aeiiia?aeaeenue ?
iaaiai?thaaeenue ia i?aeia?iaei?e iaoeia?e eiioa?aioe?? “Nia?aiaiiua
aniaeou nicaeaiey, enneaaeiaaiey e ai?iaaoeee eaea?noaaiiuo n?aaenoa”
(Oa?e?a, 1995, 1996, 1998; Eaoian, 1997), i?ae?aa?iiaeuei?e
iaoeiai-i?aeoe/i?e eiioa?aioe?? “Aeooaeuei? ieoaiiy oa?iaoeaaoe/ii? oa
iaaee/ii? iaoee oa i?aeoeee” (Caii??aeaey, 1995, 1997, 1998),
iaoeiai-i?aeoe/i?e eiioa?aioe??, i?enay/ai?e 15-??//th oa?iaoeaaoe/iiai
oaeoeueoaoo ss?ineaanueei? aea?aeaaii? iaaee/ii? aeaaeai?? “Ninoiyiea e
ia?niaeoeau nia?aiaiiiai eaea?noaiaaaeaiey” (ss?ineaaeue, 1997),
iaoeiai-i?aeoe/i?e eiioa?aioe??, i?enay/aiie 75-??//th Oe?OA (Oa?e?a,
1996).

Ioae?eaoe?? ca oaiith aeena?oaoe??. Ca iaoa??aeaie aeena?oaoe??
iioae?eiaaii 15 i?aoeue, a oiio /ene? 5 noaoae o oaoiaeo aeaeaiiyo.

Ianya ? no?oeoo?a aeena?oaoe??. Aeena?oaoe?eia ?iaioa aeeeaaeaia ia 144
noi??ieao ae?oea?nueeiai oaenoo oa neeaaea?oueny c? anooio, iaeyaeo
e?oa?aoo?e, 3 aeaa aeanieo aeine?aeaeaiue, caaaeueieo aeniiae?a ? nieneo
e?oa?aoo?e, yeee aeeth/a? 200 aeaea?ae, na?aae ieo 74 ?iicaiieo. ?iaioa
?ethno?iaaia 20 oaaeeoeyie, 12 iaethieaie.

iniiaiee ci?no ?iaioe

1. Aca?iiae?y 1,2,4-o?eacie?i-5-o?ii?a c aaeiaaiaeeaiaie,
aeeaaeiaaiaeeaiaie, aaeiaaiaaoa?ioeeeeaie ? ai?iaie.

Iio?aei? 3-R-5-o?i-1,2,4-o?eacieo oai?aoe/ii iiaeooue ?nioaaoe a i’yoe
oaooiia?ieo oi?iao. Ca aeaieie e?oa?aoo?ieo aeaea?ae a?aeiii, ui a
oaa?aeiio noai? o iaeo?aeueieo, eoaeieo ? eeneeo ?ic/eiao
3-R-5-o?i-1,2,4-o?eaciee ?niothoue ia?aaaaeii a oi?i? o?ii?a.

Oaeei /eiii, oai?aoe/ii aee?ethaaiiy 3-R-1,2,4-o?eacie?i-5-o?ii?a iiaea
i?ioiaeeoe ye ii aoiio acioo, oae ? ii aoiio n??ee c ooai?aiiyi i’yoe
?iaeea?aeoaeueieo niieoe aai ?o noi?o?.

Aeey ae??oaiiy ieoaiiy i?i iai?yi ?aaeoe?? aee?ethaaiiy
1,2,4-o?eacie?i-5-o?ii?a iaie i?iaaaeai? eaaioiai-iaoai?/i? ?ic?aooiee
iieaeoee 5-o?i-1,2,4-o?eacieo ? eiai oaooiia?ii? oi?ie a ?aieao
p-aeaeo?iiiiai iaaeeaeaiiy (iaoiae Ia??ca?a-Ia??a-Iiiea (III)).

?ic?aooiee iieacothoue, ui aia?aaoe/ii a?eueo aea?aeiith yaey?oueny
iieaeoea 5-o?i-1,2,4-o?eacieo.

Iaea?eueoa aeaeo?iiia aonoeia ciaoiaeeoueny ia aoii? n??ee (-0,363)
1,2,4-o?eacie?i-5-o?iio. Aoiie acioo N1, N2 ? N4 iathoue a?eueo iecueeo
aeaeo?iiio aonoeio.

Oiio aee?ethaaiiy 1,2,4-o?eacie?i-5-o?ii?a i?ioiaeeoue ii a?eueo
aeaeo?iiaaaoeaiiio aoiio n??ee c ooai?aiiyi a?aeiia?aeieo
S-aee?eiio?aeieo.

Aee?ethaaiiy 3-i-i?ii?e-1,2,4-o?eacie?i-5-o?iio i?iaiaeeeinue a
iaeo?aeueiiio, aai eoaeiiio na?aaeiaeu? aaeiaaiaeeaiaie (i-aooeeeiaeeae,
i-ai?eeiaeeae, ?ciai?eeiaeeae, i-aaeneea?ii?ae, i-ieoeea?ii?ae,
i-iii?ea?ii?ae, i-aeaoeeeoei?eae, aaiceea?ii?ae).

O aeiaaeeo, yeui ?aaeoe?y i?iaiaeeeanue a iaeo?aeueiiio na?aaeiaeu?,
?aaeoe?eio noi?o iaeo?ae?coaaee aiaeiei ?ic/eiii iao??th
a?ae?iea?aiiaoo, ?ic/eiiee aeia?ththoue. Aeo?ae i?iaeoeo?a ?aaeoe??
neeaaea? 40 — 85% (noaia 1).

Noaia 1

A ?*-niaeo?ao niieoe a?aenooi? nioae iiaeeiaiiy, oa?aeoa?i? aeey
eieeaaiue o?iiii? a?oie (1400 — 1300 ni-1) ? i?enooi? nioae eieeaaiue
NH-a?oie a iaaeao 3300 — 3200 ni-1.

?iaeea?aeoaeuei?noue neioaciaaieo niieoe i?aeoaa?aeaeaia ca aeiiiiiaith
oiieioa?iai? o?iiaoia?ao??.

C iaoith iiooeo a?ieia?/ii aeoeaieo niieoe iaie aea/aia ?aaeoe?y
iio?aeieo 1,2,4-o?eacie?i-5-o?iio c aeea?iiaoaiii.

sse a?aeiii, oai?aoe/ii ?aaeoe?y 1,2,4-o?eacie?i-5-o?ii?a c
aeea?iiaoaiii iiaea i?ioiaeeoe iaiaeiicia/ii c ooai?aiiyi
?iaeea?aeoaeueieo 1,2,4-o?eaciei-(2,3-a)-,
1,2,4-o?eaciei-(3,4-a)-o?acie?i?a, b-a?iiaoeeo?i-1,2,4-o?eacie?a oa
1,2-aee-(1,2,4-o?eacie?eo?i)-aoai?a aai noi?o? oeeo niieoe.

I?e i?iaaaeaii? iaie ?aaeoe?? 3-iaoee-1,2,4-o?eacie?i-5-o?iia c
aeea?iiaoaiii a eoaeiiio na?aaeiaeu? ye iniiaiee i?iaeoeo ?aaeoe??
aeae?eaii 1,2-aee-(3-iaoee-1,2,4-o?eacie?i-5-o?i)-aoai.

I?e i?iaaaeaii? ?aaeoe?? c aeea?iiaoaiii a iaeo?aeueiiio na?aaeiaeu?
iaie ye e?ioeaaee i?iaeoeo ?aaeoe?? oaeiae aeae?eaii
1,2-aee-(1,2,4-o?eacie?e)-5-o?iaoaie (noaia 2).

?iaeea?aeoaeuei?noue niieoe 1,2-aee-(1,2,4-o?eacie?e)-5-o?iaoai?a
i?aeoaa?aeaeoaaeanue iaie ca aeiiiiiaith oiieioa?iai? o?iiaoia?ao??, a
?o aoaeiaa – ca aeiiiiiaith ?*-niaeo?ineii?? ? ian-niaeo?iiao???.

Noaia 2

VII a) R=H; R1=H ae) R=C6H4=OH-O; R1=H

a) R=CH3; R1=H a) R=C6H4-NO2; R1=H

a) R=C3H7; R1=H ?) R=4-i??eaeee; R1=H

a) R=C6H5; R1=H ae) R=C6H5; R1=C6H5

Iio?aei? i??eaeeio, o?iie?io, ae?eaeeio, io?eio ciaoiaeyoue oe?iea
canoinoaaiiy a iaaee/i?e i?aeoeoe? ye i?ioei?e?iai?, i?ioea?eaeia?,
i?ioeiaey??ei?, aiaeueaaoe/i? oa i?ioecaiaeuei? caniae.

A inoaii?e /an na?aae iio?aeieo 1,2,4-o?eacieo ciaeaeai? ?a/iaeie, ye?
i?iyaeythoue aenieo aiaeaioe/io, iae?ieaioe/io, ae?o?aoe/io,
aiaeueaacoth/o oa i?ioea??onio aeoeai?noue.

Oiio ii?aeiaiiy a iaei?e iieaeoe? iio?aeieo o?iie?io, ae?eaeeio, io?eio
c iio?aeieie 1,2,4-o?eacieo ia? oai?aoe/iee oa i?aeoe/iee ?ioa?an.

Iaie aca?iiae??th 1,2,4-o?eacie?i-5-o?ii?a c 2-oei?o?iie?iii,
5-i?o?i-8-oei?o?iie?iii, 9-oei?ae?eaeeiii, 2-iaoee-9-oei?ae?eaeeiii,
2-aoiene-6-i?o?i-9-oei?ae?eaeeiii, 2-oei?aaic?i?aeacieii,
2,6-aeeoei?-7-iaoeeio?eiii io?eiai? 5-aaoa?eeo?i-1,2,4-o?eaciee (2.27 —
2.50) (noaia 3).

Noaia 3

V a) R=o-HO-C6H4; R1=H; Het=o?iie?e-2 X=Cl, Br

a) R=CH3; R1=H; Het=5-i?o?io?iie?e-8

a) R=H; R1=H; Het=ae?eaeei?e-9

a) R=CH3; R1=H; Het=ae?eaeei?e-9

ae) R=-C3H7; R1=H; Het=ae?eaeei?e-9

a) R=C6H5; R1=H; Het=ae?eaeei?e-9

?) R=o-HO-C6H4; R1=H; Het=ae?eaeei?e-9

ae) R=n-O2N-C6H4; R1=H; Het=ae?eaeei?e-9

c) R=4-i??eaeee; R1=H; Het=ae?eaeei?e-9

?) R=CH3; R1=H; Het=2-iaoeeae?eaeei?e-9

e) R=H-C3H7; R1=H; Het=2-iaoeeae?eaeei?e-9

e) R=n-O2N-C6H4; R1=H; Het=2-iaoeeae?eaeei?e-9

i) R=4-i??eaeee; R1=H; Het=2-iaoeeae?eaeei?e-9

i) R=H-C3H7; R1=H; Het=2-aoiene-6-i?o?iae?eaeei?e-9

i) R=o-HO-C6H4; R1=H; Het=2-aoiene-6-i?o?iae?eaeei?e-9

i) R=n-O2N-C6H4; R1=H; Het=2-aoiene-6-i?o?iae?eaeei?e-9

?) R=4-i??eaeee; R1=H; Het=2-aoiene-6-i?o?iae?eaeei?e-9

n) R=H; R1=H; Het=aaic?i?aeacie?e-2

o) R=CH3; R1=H; Het=aaic?i?aeacie?e-2

o) R=n-O2N-C6H4; R1=H; Het=aaic?i?aeacie?e-2

o) R=H; R1=H; Het=2-oeie-7-iaoee-io?ei?e-6

o) R=C2H5; R1=H; Het=2-oeie-7-iaoee-io?ei?e-6

oe) R=C3H7; R1=H; Het=2-oeie-7-iaoee-io?ei?e-6

/) R=4-i??eaeee; R1=C6H5; Het=2-oeie-7-iaoee-io?ei?e-6

sse i?aai?/iee ?ic/eiiee aeei?enoiaothoue aoaiie, aai aeeiaoeeoi?iai?ae.

Aoaeiaa 5-aaoa?eeo?i-1,2,4-o?eacie?a i?aeoaa?aeaeaia ca aeiiiiiaith
?*-niaeo?ineii??.

Eiiieaene 1,2,4-o?eacie?i-5-o?ii?a c iaoaeaie ? ai?iaie i?iyaeythoue
aenieo a?ieia?/io aeoeai?noue.

A?aoiaoth/e oeae oaeo, iaie c iaoith iiooeo a?ieia?/ii aeoeaieo ?a/iaei
neioaciaaii ?yae niieoe 1,2,4-o?eacie?i-5-o?ii?a c ai?iaie.

?aaeoe?y i?iaiaeeeanue a aoaiie? i?e iao?eaaeiio iaa??aaii? noi?o?
aeo?aeieo ?a/iaei (noaia 4).

Noaia 4

VI a) R=H; O=N(C4H9)3 ae) R=C3H7; O=ii?oie?i

a) R=H; O=ii?oie?i c) R=C3H7; O=aaiceeai?i

a) R=CH3; O=NH(C2H5)2 ?) R=C3H7; O=ii?oie?i

a) R=CH3; O=NH(C4H9)3 e) R=4-i??eaeee; O=NH(C4H9)3

ae) R=CH3; O=ii?oie?i e) R=4-i??eaeee; O=i?ia?acei

a) R=CH3; O=aaiceeai?i i) R=4-i??eaeee; O=ii?oie?i

?) R=C3H7; O=i?ia?acei i) R=4-i??eaeee; O=aaiceeai?i

Neioaciaai? iaie ?a/iaeie iano?ee? ? a aiaeieo ?ic/eiao iinooiiai
?iceeaaeathoueny c aeae?eaiiyi aeo?aeieo 1,2,4-o?eacie?i-5-o?ii?a, aiie
oaeiae ?iceeaaeathoueny i?ae ae??th i?aai?/ieo ? i?ia?aeueieo eeneio.

2. Neioac 5-ea?aieneaee?eo?i-1,2,4-o?eacie?a oa ?o iio?aeieo

A inoaii?e /an iioae?eiaaii ?yae i?aoeue, i?enay/aieo neioaco ?
a?ieia?/i?e aeoeaiino? 5-ea?aieneaee?eo?i-1,2,4-o?eacie?a ? ?o
iio?aeieo.

Aeai? a iaaaaeaieo i?aoeyo na?ae/aoue, ui
5-ea?aieneaee?eo?i-1,2,4-o?eaciee iathoue ?yae oe?iieo a?ieia?/ieo
aeanoeainoae ? ciaoiaeyoue canoinoaaiiy a iaaee/i?e i?aeoeoe? ye
?aiicaaith/?, aaiaoii?ioaeoi?i? ? ?io? caniae.

Aeoiaey/e c oeueiai, iaie i?iaeiaaeaia ?iaioa ii iiooeo a?ieia?/ii
aeoeaieo ?a/iaei na?aae 5-ea?aieneaee?eo?i-1,2,4-o?eacie?a ? ?o
iio?aeieo.

sse a?aeiii, aee?ethaaiiy 1,2,4-o?eacie?i-5-o?ii?a i?ioiaeeoue ii a?eueo
aeaeo?iiaaaoeaiiio aoiio n??ee c ooai?aiiyi a?aeiia?aeieo s-iio?aeieo.

I?e i?iaaaeaii? ?aaeoe?? 1,2,4-o?eacie?i-5-o?ii?a c oei?(a?ii)ioeoiaith,
a-a?iii?ii?iiiaith, a-a?iiianeyiith, a-a?iiaaea??aiiaith eeneioaie
ooai?ththoueny aaeiaaiaiaeiaa? eeneioe
5-ea?aieneaee?eo?i-1,2,4-o?eacie?a. A?aeiia?aei? eeneioe io?eiothoue
i?ney aeiaeaaaiiy a ?aaeoe?eio noi?o aea?aaeaioii? e?eueeino? iao??th
aoeaoaoo (noaia 5).

Noaia 5

VII a) R=H; R1=H; R2=CH2COOH X=Cl, Br

a) R=C3H7-i; R1=H; R2=CH2COOH

a) R=C3H7-i; R1=H; R2=CH(C2H5)COOH

a) R=CH3; R1=CH2-CH=CH2; R2=CH2COOH

ae) R=C6H5-NO2; R1=H; R2=CH2COOH

a) R=C6H5-NO2; R1=H; R2=C2H4COOH

?) R=C6H5-NO2; R1=H; R2=CH(C2H5)COOH

ae) R=C6H5-NO2; R1=H; R2=CH(C3H7)COOH

c) R=C6H5-NO2; R1=H; R2=CH(C4H9)COOH

?) R=C6H5-NO2; R1=H; R2=CH(C4H9)COOH

?iaeea?aeoaeuei?noue neioaciaaieo niieoe i?aeoaa?aeaeaia iaie ca
aeiiiiiaith oiieioa?iai? o?iiaoia?ao??, a ?o aoaeiaa — niaeo?aeueii.

?*-niaeo?e niieoe oa?aeoa?ecothoueny iayai?noth aeaio nioa iiaeeiaiiy,
oa?aeoa?ieo aeey ea?aiene-a?oi.

Na?aae ao???a 1,2,4-o?eacie?e-5-a-ia?eaioiea?aiiiaeo eeneio ciaeaeai?
niieoee, ye? i?iyaeythoue aenieo a?ieia?/io aeoeai?noue. Oiio c?icoi?ea
caoe?eaaeai?noue a/aieo aei neioaco oeeo niieoe ? ?o iio?aeieo.

Ao??e 1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo eeneio neioaciaai? iaie aeaiia
iaoiaeaie: aoa?eo?eaoe??th a?aeiia?aeieo eeneio ? aca?iiae??th
1,2,4-o?eacie?i-5-o?ii?a c ao??aie aaeiaaiioeoiaeo eeneio (noaia 6).

sse a?aeiii, a?ae?aceaee ea?aiiiaeo eeneio ? ?o iio?aei? ciaoiaeyoue
canoinoaaiiy aeey e?eoaaiiy ooaa?eoeueico, a??onieo ?ioaeoe?e ? ?ioeo
caoai?thaaiue.

Oiio iaie aeey iiaeaeueoiai a?ieia?/iiai aea/aiiy neioaciaaii a?ae?aceae
3-iaoee-4-ae?e-5-ia?eaioiioeoiai? eeneioe (noaia 6).

A ?*-niaeo?? oe??? niieoee i?enooiy nioaa iiaeeiaiiy, yea oa?aeoa?ia
aeey ea?aii?eueii? a?oie (1670 ni-1), a oaeiae oe?iea nioaa iiaeeiaiiy
NHNH2 –a?oie (3400 ni-1).

Iaie aeey a?ieia?/ieo aeine?aeaeaiue neioaciaai? nie?
1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo eeneio ye c iai?aai?/ieie, oae ?
i?aai?/ieie iniiaaie.

Noaia 6

IX a) R=i-C3H7; R1=H; R2=C2H5

a) R=4-i??eaeee; R1=H; R2=C3H7

a) R=4-i??eaeee; R1=H; R2=C4H9

a) R=CH3; R1=CH2-CH=CH2; R2=C3H7

ae) R=4-i??eaeee; R1=H; R2=C4H9

X a) R=CH3; R1=CH2-CH=CH2; R2=C6H4N02-n

a) R=4-i??eaeee; R1=C6H5; R2=C6H5

a) R=4-i??eaeee; R1=C6H5; R2=C6H4OH-o

a) R=4-i??eaeee; R1=C6H5; R2=C6H4Br-n

ae) R=4-i??eaeee; R1=C6H5; R2=C6H4NO2-i

a) R=4-i??eaeee; R1=C6H5; R2=C8H4OCH3-o

?) R=4-i??eaeee; R1=C6H5; R2=C6H4OCH3-i

ae) R=4-i??eaeee; R1=C6H5; R2=C6H4N(CH3)2-n

c) R=4-i??eaeee; R1=C6H5; R2=C6H3NO2-2-Br-5

?) R=4-i??eaeee; R1=C6H5; R2=C6H3OH-2-Br-5

e) R=4-i??eaeee; R1=C6H5; R2=C6H3Cl2-2,4

Aiii?ei?, iao???a? ? eae??a? nie? 1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo
eeneio neioaciaai? iaie aca?iiae??th a?aeiia?aeieo eeneio c aiii?aeii,
iao??th aai eae?th a?ae?ieneaeo a aiaeyiiio na?aaeiaeu? c iiaeaeueoei
aeia?thaaiiyi ?ic/eiieea (noaia 7).

Eaeueoe??a? nie? neioaciaai? iaie aca?iiae??th a?aeiia?aeieo eeneio ?
eaeueoe?th ea?aiiaoo i?e iaa??aaii? o aiae?.

Iaai??a? nie? neioaciaai? iaie aca?iiae??th a?aeiia?aeieo eeneio ?
iaai?th ieneaeo i?e eei’yo?ii? ia i?ioyc? 5 aiaeei aei iiaiiai ?ic/eio
inaaeo iaai?th ieneaeo.

Noaia 7

XI a) R=i-C3H7; R1=H; X=NH4 a) R=4-i??eaeee; R1=H; X=K+

a) R=i-C3H7; R1=H; X=Na+ ae) R=CH3; R1=CH2-CH=CH2; X=Na+

a) R=4-i??eaeee; R1=H; X=Na+

XII a) R=4-i??eaeee; R1=H; X=Ca2+ a) R=CH3; R1=CH2-CH=CH2; X=Mg2+

a) R=4-i??eaeee; R1=H; X=Mg2+ ae) R=CH3; R1=CH2-CH=CH2; X=Ca2+

a) R=CH3; R1=CH2-CH=CH2; X=Cu2+

XIII a) R=CH3; R1=CH2-CH=CH2; X=H2

I?aeia n?eue 3-iaoee-4-ae?e-o?eacie?e-5-ia?eaioiioeoiai? eeneioe
neioaciaaia iaie i?e aca?iiae?? iao???ai? nie? oe??? ae eeneioe c
aea?aaeaioiith e?euee?noth i?ae? noeueoaoo a aiaeyiiio na?aaeiaeu?
(noaia 7).

Ii?oie?i??aa n?eue 3-iaoee-4-ae?e-5-ia?eaioiioeoiai? eeneioe io?eiaia
i?e iaa??aaii? eeneioe c ii?oie?iii a na?aaeiaeu? aoaiieo.

A ?*-niaeo?ao niieoe ciaeaeai? nioae iiaeeiaiiy ea?aieneeao-?iio
(1780-1750 ni-1), a?oie NH (3500-3400 ni-1).

C e?oa?aoo?ieo aeaea?ae a?aeiii, ui ?e?aeaia?ae?aceaee ea?aiiiaeo eeneio
ciaoiaeyoue canoinoaaiiy a neioaoe/i?e ? aiae?oe/i?e o?i??, a oaeiae a
oaoi?oe? ye ?i?oe?aoi?e iie?ia?ecaoe??, ieanoeo?eaoi?e ? noaa?e?caoi?e
iie?ia??a.

A ca’yceo c oeei aoei aeioe?eueiei neioacoaaoe ?e?aeaia?ae?aceaee
1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo eeneio ? aea/eoe ?o a?ieia?/io
aeoeai?noue.

?e?aeaia?ae?aceaee 1,2,4-o?eacie?e-5-a-ia?eaioiioeoiaeo eeneio
neioaciaai? iaie aca?iiae??th a?ae?aceae?a
1,2,4-o?eacie?e-5-a-ia?eaioiioeoiaeo eeneio c aaicaeueaeaa?aeii ? eiai
iio?aeieie a aoaiie? (noaia 7).

?iaeea?aeoaeuei?noue niieoe i?aeoaa?aeaeaia ca aeiiiiiaith oiieioa?iai?
o?iiaoia?ao??.

A ?*-niaeo?ao ?e?aeaia?ae?aceae?a 1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo
eeneio iayai? nioae iiaeeiaiiy a?oi nNI 1720-1700 ni-1 ? a?oi nNH – 3500
– 3450 ni-1.

sse a?aeiii, 2-?e?aeai-1,2,4-o?eaciei-(3,4-a)-o?acie-3(2I)-iie
i?iyaeythoue aenieo a?ieia?/io aeoeai?noue. I?iaeiaaeoth/e iiooe
a?ieia?/ii aeoeaieo ?a/iaei na?aae iio?aeieo 1,2,4-o?eacie?e-5-o?ii?a,
?o S-cai?uaieo ? eiiaeainiaaieo nenoai ia iniia? 1,2,4-o?eacieo ie
neioacoaaee ?yae iiaeo iio?aeieo
2-?e?aeai-1,2,4-o?eaciei-(3,4-a)-o?acie-3(2I)-ii?a.

Iaie ?aaeoe??th 1,2,4-o?eacie?e-5-ia?eaioiea?aiiiaeo eeneio c
aaicaeueaeaa?aeii, ?caoeiii ? eiai iio?aeieie, a oaeiae ei?e/iei
aeueaeaa?aeii a na?aaeiaeu? ioeoiaee aia?ae?eae-ioeoiaa eeneioa, 1:4
neioaciaai? 2-?e?aeai-1,2,4-o?eaciei(3,4-a)-o?acie-3(2I)-iie (noaia 8).

A ?*-niaeo?ao oeeo niieoe ciaeaeai? nioae iiaeeiaiiy, oa?aeoa?i? aeey
NI-a?oie (1725-1690 ni-1).

Noaia 8

XIV a) R=4-i??eaeee; R1=CH-CH=CH-C6H5

a) R=4-i??eaeee; R1=CH-C6H5

a) R=4-i??eaeee; R1=i?oiiaoieneaaic?e?aeai

a) R=4-i??eaeee; R1=ia?aiaoieneaaic?e?aeai

ae) R=4-i??eaeee; R1=ia?aaeeiaoeeai?iiaaic?e?aeai

a) R=4-i??eaeee; R1=ia?aaeeaoeeai?iiaaic?e?aeai

XV a) R=CH3; R1=5-i?o?i?caoei?e?aeai

a) R=4-i??eaeee; R1=5-a?ii?caoei?e?aeai

a) R=4-i??eaeee; R1=5-i?o?i?caoei?e?aeai

a) R=4-i??eaeee; R1=1-(2-a?iiaoee)-5-iaoee?caoei?e?aeai

ae) R=4-i??eaeee; R1=1-aoeaoee?caoei?e?aeai

a) R=4-i??eaeee; R1=1-ai?iiea?aieneiaoee?caoei?e?aeai

?) R=4-i??eaeee; R1=1-aaice?e?aeai?caoei?e?aeai

3. A?ieia?/ia aeoeai?noue neioaciaaieo niieoe

C iaoith iiooeo a?ieia?/ii aeoeaieo niieoe, a?eueo?noue (94)
neioaciaaieo niieoe aoei ia?aaeaii ia a?ieia?/i? aei?iaoaaiiy.

I?ioei?e?iai? oa i?ioea?eaeia? aeanoeaino? aea/aeenue ia eaoaae??
i?e?ia?ieia?? oa a??onieia?? CAeIO (caa. eao. i?io. N?aeia A.?.); aino?a
oiene/i?noue, i?ioecaiaeueia, aiaeueaaoe/ia, ae?o?aoe/ia, aiaeaioe/ia ?
aioeieneaeaioia ae?y aea/aeenue ia eaoaae?? oa?iaeioa?ai?? c ee?i?/iith
oa?iaeieia??th Oe?a?inueei? oa?iaoeaaoe/ii? aeaaeai?? (caa. eao. i?io.
Naio?a A.A.); aioea?eoi?/ia aeoeai?noue aea/aeanue ia eaoaae??
oa?iaeieia?? Oe?a?inueei? oa?iaoeaaoe/ii? aeaaeai?? (caa. eao. i?io.
Ae?iaiaic N.I.); o?ii?/ia oiene/i?noue aea/aeanue ia eaoaae?? a?noieia??
CAeIO (caa. eao. i?io. Ne?oeia A.E.). I?e oeueiio anoaiiaeaii, ui
neioaciaai? iaie niieoee a?aeiinyoueny aei iaei aai iii??ii oiene/ieo
?a/iaei, ye? i?iyaeythoue i?ioei?e?iaio, i?ioea?eaeiao, aeai?eioth/o,
i?ioecaiaeueio, aiaeueaaoe/io, ae?o?aoe/io, aioeae?o?aoe/io,
aioeieneaeaioio, aiaeaioe/io oa aioea?eoi?/io ae?th (oaaeeoey).

Oaaeeoey

?i/iAeae aeoeaiino?E?euee?noue aea/aieo niieoeE?euee?noue niieoe, ui
ia?aaeuothoue aoaeiiE?euee?noue niieoe, ui iathoue iii??io ae?thAoaeii
ii??aiyiiy1i?ioei?e?iaia94688aoae?eaeeio
eaeoao2aeai?eioth/a361320ai?iacei3i?ioecaiaeueia391021aieueoa?ai4aiaeuea
aoe/ia391318aiaeuea?i5ae?o?aoe/iaaioeae?o?aoe/ia3635175a?iio?aceaeaae?o?
ae?ei6aioeieneaeaioia743oieioa?ie7aiaeaioe/ia21113eioa?i-aaiciao
iao??th8aioea?eoi?/ia312iiaiea?iai?ae

A?ieia?/ia aeoeai?noue neioaciaaieo niieoe

I?ei?oea: aeey 68 niieoe aea/aii EAe16, EAe50, EAe84.

Aiae?c aeaieo oa?iaeieia?/ii? aeoeaiino? neioaciaaieo ?a/iaei aeicaieea
anoaiiaeoe aeaye? caeiiii??iino? aca?iica’yceo i?ae o?i?/iith aoaeiaith
oa aino?ith oiene/i?noth, i?ioei?e?iaiith, i?ioea?eaeiaith,
aeai?eioth/ith, ae?o?aoe/iith, aiaeueaaoe/iith, aioeieneaeaioiith oa
aiaeaioe/iith ae??th.

Aeey aeiee?i?/ieo aei?iaoaaiue ?aeiiaiaeiaaia eae??aa n?eue
3-(4-i??eaeee)-1,2,4-o?eacie?e-5-ia?eaioiioeoiai? eeneioe, yea i?iyaey?
aenieo aioea?eoi?/io aeoeai?noue, iaei oiene/ia, ?ic/eiia o aiae? oa
aeinooiia aeey neioaco.

AENIIAEE:

1. Ca aeiiiiiaith eaaioiai-iaoai?/ieo ?ic?aooie?a iieaeoee
1,2,4-o?eacie?i-5-o?iio ii iaoiaeo Ia??ca?a-Ia??a-Iiiea iaa?oioiaaia
iai?aaeai?noue ?aaeoe?? aee?ethaaiiy 1,2,4-o?eacie?i-5-o?ii?a
aee?ethth/eie aaaioaie.

2. ?ic?iaeai? i?aia?aoeai? iaoiaee neioaco S-cai?uaieo
1,2,4-o?eacie?i-5-o?ii?a. Iaoiaeaie OO-, ?*-niaeo?ineii?? oa
ian-niaeo?iiao??? i?aeoaa?aeaeaia aoaeiaa neioaciaaieo niieoe.

3. Aca?iiae??th 1,2,4-o?eacie?i-5-o?ii?a c aaeiaaiaeeaiaie ?
aeeaaeiaaiaeeaiaie neioaciaaii ?yae iio?aeieo
5-aee?eo?i-1,2,4-o?eacie?i-5-o?iaoai?a. Anoaiiaeaii, a eoaeiiio aai
iaeo?aeueiiio na?aaeiaeuao ?aaeoe?y c aeea?iiaoaiii i?ioiaeeoue c
ooai?aiiyi ia?aaaaeii 1,2-aee-(1,2,4-o?eacie?e)-5-o?iaoai?a.

4. C iaoith iiooeo a?ieia?/ii aeoeaieo niieoe aea/aia ?aaeoe?y
1,2,4-o?eacie?i-5-o?ii?a c aaeiaaiaaoa?ioeeeeaie oa ai?iaie. I?e oeueiio
neioaciaaii ?yae 5-aaoa?eeo?i-1,2,4-o?acie?a ? eiiieaenieo niieoe
1,2,4-o?eacie?i-5-o?ii?a c ai?iaie.

5. Cae?eniaii neioac 1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo eeneio, ?o
ao???a ? a?ae?aceae?a. Eiiaeainaoe??th inoaii?o c aeueaeaa?aeaie
io?eiai? a?aeiia?aei? ?e?aeaia?ae?aceaee.

6. ?aaeoe??th 1,2,4-o?eacie?e-5-ia?eaioiioeoiaeo eeneio c aeueaeaa?aeaie
a na?aaeiaeu? ioeoiaee aia?ae?eae-ioeoiaa eeneioa, 1:4, io?eiaii ?yae
2-?e?aeai-1,2,4-o?eaciei(3,4-a)-o?acie-3(2i)ii?a.

7. A oiae? aeine?aeaeaiue neioaciaaii 94 niieoee, c yeeo 80 aia?oa.
Aoaeiaa io?eiaieo niieoe i?aeoaa?aeaeaia aeaieie aeaiaioiiai aiae?co,
OO-, ?*-niaeo?ineii?? oa ian-niaeo?iiao???, a ?o ?iaeea?aeoaeuei?noue
o?iiaoia?ao?/ii.

8. ?c 94 aea/aieo niieoe iaie anoaiiaeaii:

— aeey 6 (6 %) aeniea i?ioei?e?iaia ? i?ioea?eaeiaa aeoeai?noue;

— aeai?eioth/a aeoeai?noue aeey 13 (11 %) niieoe;

— i?ioecaiaeueia aeoeai?noue aeey 10 (10 %) niieoe;

— aiaeueaaoe/ia aeoeai?noue aeey 13 (11 %) niieoe;

— ae?o?aoe/ia aeoeai?noue aeey 3 (3 %) niieoe;

— aioeae?o?aoe/ia aeoeai?noue aeey 5 (5 %) niieoe;

— aioeieneaeaioia aeoeai?noue aeey 4 (4 %) niieoe;

— aiaeaioe/ia aeoeai?noue aeey 1 (1 %) niieoe

Aeey 68 niieoe aea/aia EAe16, EAe50, EAe84. An? aea/ai? niieoee iii??ii
aai iaeioiene/i?, ?o EAe50 ciaoiaeeoueny a iaaeao (1100-82,7 iea/ea).

9. Anoaiiaeai? aeaye? caeiiii??iino? aca?iica’yceo i?ae o?i?/iith
aoaeiaith, aino?ith oiene/i?noth, i?ioei?e?iaiith, i?ioea?eaeiaith,
aeai?eioth/ith, i?ioecaiaeueiith, ae?o?aoe/iith ? aiaeueaaoe/iith
aeoeai?noth.

10. Aeey aeiee?i?/iiai aeine?aeaeaiiy ?aeiiaiaeiaaii eae??ao n?eue
3-(4-i??eaeee)-1,2,4-o?eacie?e-5-ia?eaioiioeoiai? eeneioe, yea i?iyaey?
aenieo aioea?eoi?/io aeoeai?noue, ? iecueeioiene/iith, aiaei?ic/eiiith,
aeinooiiith aeey neioaco. Oey niieoea aeeth/aia a ieai aeine?aeaeaiue
eaoaae?e oa?iaeieia?? Oe?a?inueei? oa?iaoeaaoe/ii? aeaaeai?? ?
Caii??cueeiai aea?aeaaiiai iaaee/iiai oi?aa?neoaoo. Aeey oe??? niieoee
aea/ai? ie?ai? aniaeoe o?ii?/ii? oiene/iino?.

Nienie iioae?eiaaieo i?aoeue ca oaiith aeena?oaoe??

1. Aeeyiea ino?ie oiene/iinoe oeicaiauaiiuo nieae 1,2,4-o?eaciea ia
eiioiioth nenoaio e?un / Nu?oeia A.E., Iioioeeay A.E., E?eai?o/ei A.A. …
Oaa/aiei E.I. e ae?. // Aeooaeuei? ieoaiiy oa?iaoe. oa iaae. iaoee ?
i?aeoeee: Ca. iaoe. no. — Caii??aeaey, 1997. — Aei.1. — N. 256-259.

2. Aeeyiea o?iie/aneie oiene/iinoe oeicaiauaiiuo nieae 1,2,4-o?eaciea ia
eiioiioth nenoaio e?un ?aciuo aic?anoiuo ia?eiaeia / Nu?oeia A.E.,
Iioioeeay A.E., E?eai?o/ei A.A. … Oaa/aiei E.I. e ae?. // Aeooaeuei?
ieoaiiy oa?iaoe. oa iaae. iaoee ? i?aeoeee: Ca. iaoe. no. — Caii??aeaey,
1997. — Aei.1. — N. 259-263.

3. Oaa/aiei E.I. Neioac e aeieiae/aneay aeoeaiinoue
2-ecaoeie-eeaeai-1,2,4-o?eaciei-(3,4-)-oeacie-3-(2I)-iiia // Aeooaeuei?
ieoaiiy oa?iaoeaaoe/ii? oa iaaee/ii? iaoee oa i?aeoeee: Ca. iaoe. no. —
Caii??aeaey, 1997. — Aei. 2, O.?. — N. 101-104.

4. Neioac oa aea/aiiy a?ieia?/ii? aeoeaiino? nieae
1,2,4-o?eacie?i-5-o?ii?a / Iaianaiei I.?., Oaa/aiei ?.I., Naio?a A.A. e
ae?. // Oa?iaoe. aeo?iae. -1998 ?. — ? 6. — N. 57-60.

5. Iiooe a?ieia?/ii aeoeaieo ?a/iaei a ?yaeo iio?aeieo
5-aaoa?eeo?i-1,2,4-o?eacie?a / Iaianaiei I.?., Eieo ?.A., Aeiey A.N.,
Oaa/aiei ?.I. oa ?i. // A?niee oa?iaoe??. — 1998. — ? 2(18). — N. 21-25.

6. Neioac e aeieiae/aneay aeoeaiinoue S-caiauaiiuo
3-n-i?iiee-1,2,4-o?eacieee-5-oeiia / Iaianaiei A.E., Eiuo A.A., Naio?a
A.A., Oaa/aiei E.I. // Eaea?noaa-/aeiaaeo :Iaaeae. na. iao/. o?oaeia ii
nicaeaieth e ai?iaaoeee iiauo eaea?noa. n?aaenoa. — O., 1996. — O.1. —
N. 214-223.

7. Ai?enaiei I.A., Oaa/aiei ?.I., Iino?eaaiue I.?.. Neioac, aeanoeaino?
oa a?ieia?/ia aeoeai?noue iio?aeieo 4-ai?ii- oa 5-o?i-1,2,4-o?eacieo //
Na. iao/. o?. iieiaeuo o/aiuo e iaaeeeia-niaoeeaeenoia CAEOA e CAIO. —
3aii?iaeuea, 1996. — N. 85.

8. Iiooe a?ieia?/ii-aeoeaieo niieoe na?aae iio?aeieo 5-o?i-4-ai?ii- oa
4-ai?ii-5-o?i-1,2,4-o?eacieo / Iaianaiei I.?., Eieo ?.A., Aeiey A.N. …
Oaa/aiei ?.I. oa ?i. // Iaoa??aee iaoe.-i?aeo. eiio., i?enay/. 75 ??//th
Oe?OA. — O., 1996. — N. 62.

9. Neioac, naienoaa e aeieiae/aneay aeoeaiinoue 5-oei e
4-aieii-caiauaiiuo 1,2,4-o?eaciea / Iaianaiei A.E., Naio?a A.A.,
Ai?enaiei I.A., Oaa/aiei E.I. // Ninoiyiea e ia?niaeoeau nia?aiaiiiai
eaea?noaiaaaeaiey: Iaoa?eaeu iao/.-i?aeo. eiio., iinayu. 15-eaoeth oa?i.
o-oa ss?ine. Ain. Iaae. Aeaae. — ss?ineaaeue, 1997. — N. 75.

10. Ia?ae/iay ioeaiea oa?iaeieiae/aneie aeoeaiinoe caiauaiiuo
1,2,4-o?eaciea // Iooei E.I., Oeoia E.A., Oeeiaa A.A. … Oaa/aiei E.I. //
Eaea?noaa-/aeiaaeo: Iaaeae. na. iao. ii nicaeaieth e ai?iaaoeee iiauo
eaea?noa. n?aaenoa. — Eaoian, 1997. — O.5. — N. 286-294.

11. I?ioeaiainiaeeoaeueiay aeoeaiinoue caiauaiiuo 1,2,4-o?eaciea/ Ioey?
A.A., Iooei E.I., Oeoia E.A. … Oaa/aiei E.I. e ae?. //
Eaea?noaa-/aeiaaeo: Iaaeae. na. iao/. o?. V iao/-i?. eiio. ii nicaeaieth
e ai?iaaoeee iiauo eaea?noa. n?aaenoa. — Eaoian., 1997. — O.5. — N.
264-268.

12. Acaeiiaeaenoaea caiauaiiuo 1,2,4-o?eaciea n aa?aeoo?aoaie / Iooei
E.I., Oeoia E.A., Oeeiaa A.A., … Oaa/aiei E.I. e ae?. // Oai aea. — N.
273-277.

13. Aeieiae/aneay aeoeaiinoue iaeioi?uo S-caiauaiiuo
1,2,4-o?eacieee-5-oeiia / Iaianaiei A. E., Oaa/aiei E. I., Aa?aa A. A. e
ae?. // *aeiaae e aai caei?iauea :Na. iao/i. ?aaio. — Eo?ne, 1998. —
Aui.1.- N. 225-257.

14. Aeeyiea i?iecaiaeiuo o?eaciea ia aa?anneaiinoue iiaaaeaiey
aeeaioiuo / Aaeoiaiei I.A., Iooei E.I., Oeeiaa A.A. … Oaa/aiei E.I. e
ae?. // Eaea?noaa-/aeiaaeo: Iaaeaeoia?. na. iao/. o?. VI iao/.-i?aeo
eiio. ii nicaeaieth e ai?iaaoeee iiauo eaea?noa. n?aaenoa. — O., 1998. —
N. 7-9.

15. Aeeo?aoe/aneay aeoeaiinoue eiiaeaine?iaaiiuo i?iecaiaeiuo o?eaciea /
Oeeiaa A.A., Iooei E.E., Oa?oneia A.A., Iaianaiei A.E. //
Eaea?noaa-/aeiaaeo: Iaaeae. na. iao/. o?. VI iao/. eiio. ii nicaeaieth e
ai?iaaoeee iiauo eaea?noa. n?aaenoa. — O., 1998. — O.2. — N. 242.

Oaa/aiei ?.I. «Neioac, o?ceei-o?i?/i? oa a?ieia?/i? aeanoeaino? N- i
S-cai?uaieo iiii- ? a?oeeee?/ieo acaaaoa?ioeeee?a». — ?oeiien.

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa oa?iaoeaaoe/ieo
iaoe ii niaoe?aeueiino? 15.00.02 — oa?iaoeaaoe/ia o?i?y oa
oa?iaeiaiic?y. — Caii??cueeee aea?aeaaiee iaaee/iee oi?aa?neoao,
Caii??aeaey, 1999.

?ic?iaeai? i?aia?aoeai? iaoiaee neioaco iio?aeieo 5-o?i-,
5-ea?aieneaee?eo?i-, 5-aaoa?eeo?i-,
1,2,4-o?eaciei(3,4-a)-o?acie-3(2I)-ii?a. Iaea?aeaii 94 niieoee, c yeeo
80 iaiienaieo ?ai?oa a e?oa?aoo??. Ia iniia? eaaioiai-iaoai?/ieo
?ic?aooie?a ca iaoiaeii Ia??ca?a-Ia??a-Iiiea ni?iaiiciaaia
iai?aaeai?noue ?aaeoe?? aee?ethaaiiy 1,2,4-o?eacie?i-5-o?ii?a.
I?iaaaeaii oe?eani?yiiaaiee neioac a?ieia?/ii aeoeaieo niieoe na?aae
3-iiii- ? 3,4-aeecai?uaieo 1,2,4-o?eacie?i-5-o?ii?a. No?oeoo?a
neioaciaaieo niieoe i?aeoaa?aeaeaia cono??/iei neioacii, aeaieie
aeaiaioiiai aiae?co, OO-, ?*-niaeo?ineii??th, ian-niaeo?iiao???th, a ?o
?iaeea?aeoaeuei?noue — iaoiaeaie oiieioa?iai? o?iiaoia?ao??.

Aeey aeiee?i?/ieo aeine?aeaeaiue ?aeiiaiaeiaaia eae??aa n?eue
3-(4-i??eaeee)-1,2,4-o?eacie?e-5-ia?eaioiioeoiai? eeneioe, yea i?iyaey?
aenieo aioea?eoi?/io ae?th.

Eeth/ia? neiaa: neioac, 5-o?i-1,2,4-o?eacie,
1,2,4-o?eaciei(3,4-a)-o?acie, aee?ethaaiiy, niaeo?aeuei? oa?aeoa?enoeee,
oa?iaeieia?/i? aeine?aeaeaiiy.

Oaa/aiei E.I. «Neioac, oeceei-oeie/aneea e aeieiae/aneea naienoaa N- e
S-caiauaiiuo iiii- e aeoeeeee/aneeo acaaaoa?ioeeeeia». — ?oeiienue.

Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oa?iaoeaaoe/aneeo
iaoe ii niaoeeaeueiinoe 15.00.02. — oa?iaoeaaoe/aneay oeiey e
oa?iaeiaiicey. — Caii?iaeneee ainoaea?noaaiiue iaaeeoeeineee
oieaa?neoao, Caii?iaeuea, 1999.

Ianiio?y ia iaee/ea ioaeeeaoeee ii ?ac?aaioea iaoiaeia neioaca,
eco/aieth oeie/aneeo e aeieiae/aneeo naienoa 1,2,4-o?eacieei-5-oeiiia,
iiiaea aii?inu eo no?iaiey, oeceei-oeie/aneeo e oa?iaeieiae/aneeo
naienoa eco/aiu iaaeinoaoi/ii.

A nayce n yoei, eco/aiea oeiee, ?aaeoeeiiiie niiniaiinoe e caaeneiinoe
aeieiae/aneie aeoeaiinoe io no?iaiey iiauo i?iecaiaeiuo
5-oei-1,2,4-o?eacieia yaeyaony aeooaeueiui, eiaao oai?aoe/aneia e
i?aeoe/aneia cia/aiea e ioaeaeaaony a aeaeueiaeoai eco/aiee.

Iniiaiie oeaeueth ?aaiou yaeyaony iiene niaaeeiaiee n i?ioeaiiee?iaiie,
i?ioeaia?eaeiaie, aeai?aie?othuae, aeeo?aoe/aneie, aiaeueaaoe/aneie,
aiaeaioe/aneie e aioea?eoie/aneie aeoeaiinoueth n?aaee i?iecaiaeiuo
5-oei-1,2,4-o?eacieia, a oaeaea onoaiiaeaiea caaeneiinoe iaaeaeo
oeie/aneei no?iaieai e aeieiae/aneei aeaenoaeai.

Ia iniiaaiee aeaiiuo eaaioiai-iaoaie/aneeo ?an/aoia iaoiaeii
Ia?eca?a-Ia??a-Iiiea, ni?iaiice?iaaii iai?aaeaiea ?aaeoeee aeeeee?iaaiey
1,2,4-o?eacieei-5-oeiiia. I?iaaaeai oeaeaiai?aaeaiiue neioac
aeieiae/ii-aeoeaiuo niaaeeiaiee n?aaee i?iecaiaeiuo 3-iiii-,
3,4-aeecaiauaiiuo 1,2,4-o?eacieei-5-oeiiia e
1,2,4-o?eaciei(3,4-a)-oeacieia. Iaoiaeaie OO-, EE-niaeo?ineiiee,
iann-niaeo?iiao?ee e oiieineieiie o?iiaoia?aoee eco/aiu
oeceei-oeie/aneea naienoaa neioace?iaaiiuo niaaeeiaiee. ?ac?aaioaiu
i?aia?aoeaiua iaoiaeu neioaca iaeioi?uo 5-aeeeeoei-,
5-ea?aieneaeeeeoei-, 5-aaoa?eeoei-1,2,4-o?eacieia e nieae
1,2,4-o?eacieei-5-oeiiia n aieiaie e i?iecaiaeiuo
1,2,4-o?eaciei(3,4-a)-oeacieia.

Eco/aia aeieiae/aneay aeoeaiinoue ia?a/eneaiiuo auoa i?iecaiaeiuo,
onoaiiaeaia iaeioi?ay caaeneiinoue acaeiinayce aeieiae/aneiai aeaenoaey
e oeie/aneiai no?iaiey.

Neioace?iaaii 94 niaaeeiaiey, ec eioi?uo 80 aia?aua, eco/aia eo
?aaeoeeiiiay niiniaiinoue e oeceei-oeie/aneea naienoaa. Aeey
aeieeeie/aneiai eco/aiey, n oeaeueth nicaeaiey ia aai iniiaa iiaiai
eaea?noaaiiiai i?aia?aoa, ?aeiiaiaeiaaia eaeeaaay nieue
3-(4-ie?eaeee)-1,2,4-o?eacieee-5-ia?eaioioenoniie eeneiou, eioi?ay
i?iyaeyao aunieoth aioea?eoie/aneoth aeoeaiinoue e ieceoth oiene/iinoue.

Eeth/aaua neiaa: neioac, 5-oei-1,2,4-o?eacie,
1,2,4-o?eaciei(3,4-a)-oeacie, aeeeee?iaaiea, niaeo?aeueiua
oa?aeoa?enoeee, oa?iaeieiae/aneea enneaaeiaaiey.

Shevchenko I.N. «Synthesis, physical-chemical and biological properties
of N- and S-substituted mono- and bicyclic azaheterocycles». —
Manuscript.

Dissertation for the scientific degree of candidate of pharmacy in
speciality 15.00.02 — pharmaceutical chemistry and pharmacognosy,
Zaporozhye State Medical University, Zaporozhye, 1999.

Preparative methods for synthesis of 5-thio-, 5-carboxyalthio-,
1,2,4-triasol(3,4-b)-thiasole-3(2M)-onov derivatives have been worked
out. We have got 80 (non-informed in literature previously) compounds on
the basis of quantum-chemical estimates by Parizer-Parral-Paple method
and prognosticated the direction of 1,2,4-triasoline-5-thiones
alkylation reaction. The purposeful synthesis of biologically active
compounds among 3-mono- and 3,4-disubstituted 1,2,4-triasoline-5-thiones
have been performed. The structure of the synthesized compounds was
confirmed by counter syntheses, elemental analyses data, UV-,
IR-spectroscopy, mass spectrometry and their individuality — by thin
layer chromatography methods. Potassium salt
3-(4-pyridil)-1,2,4-triasolil-5-mercaptoacetic acid having a high
antiarrythmia activity was recommended for preclinical investigation.

Key words: synthesis, 5-thio-1,2,4-triasol,
1,2,4-triasol(3,4-b)-thiazole, alkylation, spectral characteristics,
pharmacological studies.

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