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NHAc NHAc NHAc H2O2, H H Na2WO4, H3POO O AcOH H H H H 108 109 Oapyoc, o cooae AcOH aece pacope eco eaoa po ooy pepae cxox aeao poy cyae cooa eaoa peaoo cec cea ocaaoc epopeapoaee cxooe eeco. O aopo, ocx o ee, ooo, ec ya pacopoc ooeo aaaopa AcOH.

B yao e oooo xpoaopae yaoc e poy 109. peoaae eo cec oe oceo oe ocyoc oo c oeea aa mpac-apae apoy aece.

a ceaa oa pe ao cyae oce a ocoe H2O2 MeCN, oao, ec aaac eaea oepc cxooo aa (< 25%).

oyea cec oce 109 110 c e a a opaoaa e paee paaeo cepo coo eax ycox, o peo opaoa c o xoo 62 % cec yx coeco pcayxc oo, oop pca cpyyp 111, 112.

H H 30% H2SOCec 109, CH2ClN N H H OH OH Ac Ac 111 cxo peooe o mpac-pacp ocpaooo a aoo aoa eeco 111 opayec 109, a eo oep 112 110 peyae ucpacp.

Ocee oyeo cec xpooo coo aeoe po opaoa eoa 113 co 114, c xoa 31 24 %.

CrO3, H2SOCec 111, COOH CH3COCHN N O O Ac Ac 113 (31 %) 114 (24 %) poooe opmo-oya 115 p ec H2O2 AcOH pepaaec eocpeceo o 116 c xoo 70 %, oc pcycye ceox oecax. Opaoae eceoo poya a ocec ae o-eo py, oaae ae aece o apae aeoy paey, e ca po acoy papoa oceeo, o yeae co epox apae aa c C=C oeo ace opaaoo peaea. B peyae opayec oo o oc yx oox, oop peecye oy 116.

H NHAc H2O2, CHNa2WO4, H3PON AcOH H OH CH3 Ac 115 116 (70 %) oeceoe poooe 117 ex e ycox pepaaec cec oa 118 apaoa 119 (paee xpoaopaec) c xoa 29 36 %. peooeo 119 opayec poeyooo mpac-oca 119a, uc-oca 118a aaa aoa aoa a ao C(2) apyea cece pocpaceo yaeoc p aoec eo c H2O opayec o 118.

H NHAc H CHO NHAc N H CHCH3 Ac OH H2O2, H H Na2WO4, H3PO119a 119 (36 %) NHAc AcOH NHAc H H CH117 CHO OH OH H H H H a 118 (29 %) Cec poyo oce aaox ycox N-ae-2-(oec-2e)aa oaaac coo, pae ee epoa ooe e paee e yaoc.

Ta opao, poeeoe cceoae oaao e aece ooe 6 pa aa a peya poecca oce oae-2-x cycpao, acoc, a cepeoceeoc opaoa epoo oeoo ocoo poya a eo cocooc a.

8. Ce eoopx poox a ocoe poyo oce C e oye coo a ocoe opmo-(ae)apao aee eepoa ye coc oyex coee oye p oco, oope oepy epepypoe ycox eaa.

eo 38 pepae ece pocaa oc 120 (xo %), oop oepy ec xopcoo oa eexope p 0C. p o oaoc pacpee a oooo aece c opaoae aaa 121. Oao eceoc aaac paea o eay, pea py 122 c xoo 45 %. Opaoae oceeo ocec oeo cooc papy c C(1)N aoa J cece -oopoo ea eoo aece.

NHMs N O H NHMs NHMs NH2OH. HCl, SOClNaHCON NHMs OH CH2ClMeOH N CN OH (CH2)(86 %) J (45 %) eocao 32 pepae c xoo 68 % eo 123 ece CrO3 aeoe cx ycox. aee ece poxopa pocaa pcyc co c xoo 83 % oye oc 124. Opaoa oceeo SOCl2 CH2Cl2 pea opaoa eopa 125 (xo 35 %, aaec coe ocoee).

OH O N N NH2OH. HCl, CrO3, H2SOO O O NaHCO3 SOClMe2CO CH2ClMeOH N O N O N O H H H Me Me Me 124a (83 %) (68 %) NH2 O N N - COO O (CH2)3CN N O N O H H Me Me 124 (35 %) B ao cyae, a peye, pocxo epepypoa epoaao opaoaeoc o ece SOCl2 aoa 124a c pacpee eoo oa. C C(1)N oa 124 ocaea a -oop eo eo py, a p-oop ece aoa copoa, eco opaoa aaoo a pocxo ee pap, a eop epea 124, pepaac oe poy.

eo 113 opaye oc 126, oop ycox epepypo eaa opaye poooe oa c xoo 66 %. Peya epepypo yaae a amu-pacooee poc ao C(3a), epea K capyec o e c papo ao C(3a)N c, aa poy eco oooo aaa 128.

NH2OH. HCl SOClNaHCOCH2ClCH3OH N N N N OH Ac Ac (84 %) N N O H Ac -H+ CN CN N N N N Ac Ac Ac 127 (66 %) K Ta opao, oeee ycox pea eaa yex oco ee oy epy opaoae ecx apoaox cpyyp, cox pacee cece oopoo ea peax c yepoao aecee.

9. Peya ooecx ca aopaope oo pace cya oo H PAH poee ca 2-poc-8-ecpo[(4H-3,1-eoca-2-o)-4,1oeaa] (32), 5-(2-eapocao-3-ee)-5-ocoeaoo co (104), cec N-ae-3-poc-1,2,3,3a,4,8becapooea[b]oo (111, 112) a pee a pocpeypye cocooc. Beeco 104 oaae aoee pae oaae:

p oepa peeoo pacopa 0.1 / ppoc eca oeo coca 50 %, eca ope 28 %, oeo 15 %, a opao, o coeee ec epce oee yyeoo ye.

BBO 1. oaaa paea acoc apae pea N-a-2(oee-1-)ao c H2O2 o a aece p aoe, a 6eo py apoaeco pe, a aaaopa ( copeaea), opayx ceeo 3,1-eoca, oc, o p appoa x aopo.

2. Oapyea eaea yceoc N-apoox o(oece-1-)ao ee epecex ye 1 ypoeypx aopo a peaeo, pooe a 3,1eocaoe poy c xoa 3253%.

3. Cyoa 2-(oae-1-)ao opay ycox oce poy aoec co cpeo epepypo epoo oca oop oo, ae cp eo.

4. N-a-2-(1-e-1-ye)a a peax c H2O2 coee 3,1eocaooo pa oc acoc o cpoe yco poee pea.

5. caoeo opaoae po oo c xoa 4547 % aece eceoo a ycox poyo oce H2O2 pcyc aeopa O-apoox opmo-(oee-1-)eoa.

6. caoeo, o ocee N-ae-2-(oae-1-)ao aypao coo po pacp aeoo a c opaoae eoco c xoa 5962%.

7. Ocee N-ae-2-(oee-1-)aa eocpao ClOpo opaoa 3,1-eocao. B ocee cyae opayec ae opo poy - N-ae-2-(5-oco-1-oee)a.

8. oaaa acoc a poyo aoec N-ae-opmo(oee-2-)ao c H2O2 /Na2WO4,H3PO4 o a 6-eo py apoaeco oe: oeeoe poooe, e coepaee 6-ey pyy, ae cec yx oco, a ecoepaee coeee ae poy a poeyooo oca - o, aece eceoo poya.

9. caoeo poeae epepypo eaa oco poox poyo oce aeapao c ypoeypo paeae c opaoae po cece oeo cooc papy c CN apoaoe, opayec oce pa yepoa, a ce epoooopoo ea cocee py (p-oop eepoaoa oop apoaecoo pa).

Ocooe coepae ccepaoo pao oeo ceyx yax:

1. aay P. P., Hacpo M. ., Bpae E. M., oa O. B., Apaxao . . Ce N-(opmo- napa-aee)coepax xao-4-oo // ypa p. x. 2001. B.6. C.963 965.

2. Gataullin R. R., Nasyrov M. F., Shitikova O. V., Spirikhin L. V., Abdrakhmanov I.

B. Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide // Mend.

Commun. 2001. 5. P. 200201.

3. aay P. P., Hacpo M. ., eo . ., axo A. A., oa O.

B., Cpx . B., Apaxao . . Ocee N-a-2-(oa-1e)ao ooo epoco oopoa // . AH Cep. x. 2002. 1. C. 118121.

4. aay P. P., Hacpo M. ., aoa E. B., aaoa H. H., Apaxao . . eocpa a o peae oye eocao // ypa op. x. 2002. B.5. C.799800.

5. Hacpo M. ., aay P. P., Apaxao . . Ocee N-a-2(oa-1-e)ao epec oopoa // Tec oao V ooeo ayo o-oepe o opaeco x. - Eaepyp, 2002. C.314.

6. aapoa . P., Hacpo M. ., aay P. P., Apaxao . . paea o eay ooo e opmo-aeeoo oya // Tec oao oepe oox yex, acpao cyeo, oceo 40-e xecoo ayea. a, 2002. C.118.

7. Hacpo M. ., aay P. P., Apaxao . . Ocee N-a-2(oec-1-e)ao eoop ocpy peaea // Opaec ce oo coe: Maepa pee ooeo ooepe o opaecoy cey (YSCOS-3). - Ca-eepyp, 2002. C.354.

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