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Ha paax pyoc HACPOB MAPAT APTOB PEBPAEH POBOHX OPTO(AEH)AHHOB O ECTBEM OCTEE HA OCHOBE EPOCA BOOPOA Ceaoc 02.00.03 Opaeca x ABTOPEEPAT ccepa a cocae yeo cee aaa xecx ay A 2002 2 Paoa oea a aepe ox exoo poooecx pooc coo ocyapceoo eoo execoo yepcea aopaop eepoecx coee cya opaeco x coo ayoo epa Poccco Aae ay.

Hay pyooe oop xecx ay, poeccop Apaxao yc apee.

Hay ocya: aa xecx ay, cap ay copy aay Pa Paao.

Oae ooe: oop xecx ay, poeccop oc Cee Coooo.

aa xecx ay, cap ay copy Cyaoa Pa Mapceea.

Beya opaa cy eex aaa Aae ay pecy aop oca coo ayoo epa Poccco Aae ay aa ccepa cococ 10 eap 2002 oa 10.30 a acea ccepaooo coea 212.289.01 p co ocyapceo eo execo yepcee o apecy: 450062, Pecya aopoca, . a, y. ocoao,1.

C ccepae oo oaoc oee coo ocyapceoo eoo execoo yepcea.

Aopeepa paoca _ op 2002 oa.

e cepeap ccepaooo coea Cp A. M.

3 OA XAPATEPCTA PAOT Ayaoc pao. Opmo-aeapa c eoocy poya ao-epepypo ea, ocoeoc o acaec o-(1-e-2-ye)- o-(oee)ao, oyaex poeo ocyx epea oeaea. pooe yaax ao c oypoya cee aaoo, peapao c yo ecoaecepye aoc, e oo oea cee aocoepax eepoecx coee, o ocyo oo aaa cceoa o oac. eec p pepo eepoa aeao o ece -oye, aoeo cox aaaopo c opaoae coee eocaooo, oooo, xoaooo pa xoo. B o e pe cee o yoaa eepoa ocyaex cycpao p ec copocoepax ocee, o ce epec oopoa eca opae, ayaoc ao pao oycoaec eoxooc papao ax eoo c xoo a oe oeao ooec ae coee x peece.

Paoa oea paax aox cceoa cya opaeco x coo ayoo epa Poccco Aae ay, poeex cooec c eo Papaoa ox eoo apaeo eepoa aeapao (oep ocyapceo pecpa 01.20.00) cooec c popao ocyapcea oepa epa ceo opaoa yaeao ay a 1997-2000 . (opa A 0005).

e pao. cceoae poecco oce pax Naeex poox opmo-(ae)apao peaea a ocoe epoca oopoa, yee aopo, x a cpoee poyo; ee oooce apaeo eepoa yaex cycpao ycox oce.

Haya oa pao. Bepe ece ocee a ocoe epoca oopoa a pooe o-(ae-1-)apao poeea x a yoapoae 3,1-eoca.

poeocppoaa acoc cpoe poyo oce aopa o(ae-1-)apao o ceyx ypoeypx aopo: a opmo-aece apoaeco pe aa, a paaa p aoe aoa, cpoe aeoo aece, ooa apaeo cepoa a ocoe yaex cycpao 3,1-eoca, oc, o eo.

caoeo e a peeo oceo cce a ocoe epoca oopoa a cpoee poyo pepae o-(ae-1)apao.

oaao, o p oce epoco oopoa pcyc aeopa O-apoox opmo-(oee-1-)eoa ece o poyo c p oo.

Bepe yea pea oce N-ae-2-(oae-2)ao peaea a ocoe epec oopoa oaaa acoc cpoe poyo o xapaepa aee apoaecoo pa.

paeca eoc. peoe peapae eo cea eoocyx o-(ae-1-)apao coee 3,1-eocaooo oooo pa; peoe eo yoaa o-(a-1e)ao o aeoy aece ece H2O2 c oyee oco, eoo, po oo apao, coepax opmoeoco ocao.

Oapyea cocooc eoopx oyex coee peypoa poc pace (o a cceoa, poeex aopaop oo pace cya oo H PAH).

Apoa pao. Peya ccepaoo pao oaac a oepe oox yex, acpao cyeo, oceo 40e xecoo ayea (a, 2002), V ooeo ayo oeoepe o opaeco x (Eaepyp, 2002), pee ooeo oe-oepe o opaecoy cey (YSCOS-3) Opaec ce oo coe (Ca-eepyp, 2002).

ya. o ee ccepa oyoao 4 ca, ec 3 oao.

Cpyypa oe pao. ccepaoa paoa oea a cpaax aocoo eca ae eee, oop epayp, ocyee peyao, cepeay ac, o, cco epayp (aeoa), poee.

OCHOBHOE COEPAHE PAOT 1. pepae opmo-(oee-1-)apao o ece H2OOpmo-aea peca coo coee, ee yeo ep ao aoa, eocpeceo oc o oo c aeoo aece, o peoaae oooc ypoeypo a p aae epox peaeo c opaoae - ecex ecx cce. B yex a peax oce poox opmo-(a-1-e)ao epec oopoa oapyeo e a eee poecca a aecee apoaecoo pa, a ax py y aoa aoa, x, o-epx, a cee eo ocooc, o-opx, oox ec ooe yeo ep.

Oco cocoo cea oco ec opaoa aeo acoa, oao ocee oaa po eocao eycooc oca x p xpae, cpaea cooc pooe pooacoc oeppoax pacopo. o o pe a pa ocee cce a ocoe paaeo H2O2 pcyc aaaopa o copeaea. B aece epo oceo cce a peea epec oopoa pcyc aaecx oec Na2WO4 H3PO4 (ccea I), opayc p aoec ooeo oec ec ocpy aeo. B aece opoo oce a cooaa epec oopoa pcyc aeopa ccea aa (ccea II). B ao cyae ocpye ace ec aaeoa coa, opayac peyae pcoee H2O2 oeye aeopa p ec ocoa.

Aea 79 oye aoece cooecyx ao 46 c Ac2O CH2Cl2 c xoa 9197 %, oope co oepe, opayc p oepa oe-2-ex 13 poox p e c OH (xo 7395 %). Ocee ao 79 cceo I po opaoa 3,1-eocao 1012 c xoa 6573 %. Oeo, poeyo poyo ec oc, oop cpo yec oe poy.

R R R Ac2O KOH NH2 CH2ClNHAc NH2 300oC, 1 4-6 (73-95 %) 7-9 (91-97 %) H2O2, 1-Na2WO4, H3POO 4' 3' HO 5' 2' MeOH R R 5 O O 4a 7 8a 8 N CHN CHH 10-12(65-73 %) R=H (1, 4, 7, 10), R=Me (2, 5, 8, 11), R=OMe (3, 6, 9, 12) Ao copoa eocaooo a pocoo ocaa pacooe o pae copo ococ oeaooo oa, ec cxo peooe o cxpox o oopeex pape c C(1) O ocpaoo e aae aoa copoa aeo py.

Aepooe 2-oya 2,4-ca 17, 18 oye aaoo coee 79 oepae 13, 14 c ocey apoae poyo 15, 16. p oe ec eocay pea coee aex oec poyo pea oapyeo e o. o-oy, o oycoeo pocpace apyee aa oce ac, a a oox aax eec opmo-ea pya ee ae yeae cee paaeo coo aeopy, oopa, co oepe, papye oy c.

NH2 NHNHAc Me Me Me H2OAc2O KOH CH2Cl300oC, 1 Na2WO4, H3POR R R 13, 14 15, 16 (8895 %) 17, 18 (9094%) R=H (13, 15, 17), R=Me (14, 16, 18) aa 79, 17 a peea ae ccea aa. A 79 ao cyae a e e poy, o cyae ec cce I. Coeee 17 ao cyae pea cyae ( oe o cya c cceo I), opay 3,1-eoca 19 c xoo 66 %.

HO H2O2, O MeCN, OHMeOH N CHNHAc Me Me 17 19 (66 %) Ocyce opmo-aece ocec e, o oeya aoo co ee e paep, e ocopoopaa oec (ccea I), o oeae ee pee oo c.

aea aeo py p aoe aoa a ocapoy caaec a peyaax oceo a. ocapo aece oc ece xopopaa a cooecy a 46 pcyc K2CO3 (xo poyo 2022 9095 %). Ocee poox 20 22 cceo I po opaoa 3,1-eoca-2-oo 2325 c xoa 6975 %. Haaec oep oo paea ocopo py.

HO H2O2, R R EtOCOCl, R Na2WO4, H3POO K2COMeOH CH2ClNH2 N O NHCOOEt H 4-6 2022 (9095%) 2325 (6975 %) R=H (4, 20, 23),R=Me (5, 21, 24), R=OMe (6, 22, 25) peee aa 20, 21 epec oopoa aeope pcyc OH po opaoa N-ocop-3a-poc-1,2,3,3a,4,8becapooe[b]oo 26, 27 (xo 7075 %), o oopx (26) epapoa ece oocopo co eee 15 p oao eepaype o 28 (90 %).

H R H2O2, MeOH 6 8a8b 3a O 20, 4a O 8 OH MeCN, OHN N 20oC, 15 NHCO2Et NHCO2Et COOEt COOEt A B 26, 27(7075 %) 28 (90 %) R=H (26), R=Me (27) peooeo opaoae oo a 26,27 cao oo cece epepypo poeyooo oca A eo B (ooe epepypo aco cpeac p ocpoa). oce peepeae aee a o peyae ypoeypo yeoo aa aoa aoa o yepoy apoo py.

2-(oe-1-e)-6-eoca 29 oye aaoo 4 c xoo 54 % apoa EtOCOCl pcyc 2CO3 eexope (xo coee 31 89 %). Ocee ocapox poox 30 31 cceo I po, a cyae poox aa, eoca-2-oa 32 33 c xoa 7578 %.

HO H2O2, EtOCOCl, Na2WO4, H3PO4 O K2COMeOH NH2 CH2ClN O NHCOOEt H R R R 15,29 30, 31(89 %) 32, 33 (7578 %) R=Me (15, 30, 32), R=OMe (29, 31, 33) p pee e coee 30,31 cce II opayc 2-oc3,1-eoca 34, 35 (xo 6063 %). ec, oe o peyeo cya, oep oo paea ao py e pocxo, o, o oycoeo ypoe cooc cpe.

HO H2O2, MeCN, OH- O MeOH NHCOOEt N OEt R R 30,31 34, 35 (6063 %) R=Me (30, 34), R=OMe (31, 35) Ceye oe, o 6-e- 6-eocaeee pooe ey ce oaoo ycox pepae, ecop a ecy pay ee ae coaaex aece eoepx yox eo, oopa, oeo, epyec a ema-pacooee ooceo aeoo aece, a yaeoc. Cepecoe e ax aecee a xo pea, a o, oaoo.

peee cyox ax py p aoe aoa aeaa ooo oy o poyo ee peyx cyax.

p oce eacyooo 36 napa-oyocyooo 37 poox o-oya (oye opaoo aa 15 cooecy xopapo pe) cceo a ocoe aeopa ece poya pea c eo 38, 39 (xo 6062 %). x opaoae oepae ceaoe paee peooee o eoo epeae B pea, eye oa 26, 27.

NHSO2R NHSO2R NHH2O2, RSO2Cl Me MeCN, OH- Me Me MeOH Py O 15 36, 37 (86 %) 38, 39 (6062 %) R=Me (36, 38), R=napa-CH3C6H4 (37, 39) B ao cyae epoaao opayc p oce aea oc e oe peepe a cpyypy ocaooo a, ooy oe epo ye caa oo eycooo poeyooo poya ec epepypoa eo eo.

Bo, o ao py (oa ea) e oaae a cpoee poyo, e oee, o xo oox cyax cpa. Bo, pae eoepo yo aece p cyopye (CH3 n-CH3C6H4) ee ao cyae eooe aee cece yaeoc eo o peaooo epa.

p oce poox aa apa oaaec oee coo, pe oa cyoaa 40, 41 (ea oa, oye 4 aaoo 36, 37, xo 8492%) ey ce oaoo, aa cec epex poyo. Bepoo, opooy oc epea C peepeae pacpe ocpaooo oa c opaoae aoa D, oop aco epepypoaec eo epea E, aee yc o (42, 43). epea D oe capoac ae o axao eoc-oa cpe, o poco pooa, peyae poea epoo poecca opayc p 46, 47 48, 49, epoopoae e ae ae cp 44, 45.

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