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oa 1-xopae-4-n-eoce- 1-xopae-4-npoeceapa (12, 13) e yaoc. Bappoae eepaypo, pooeoc pea oop pacopee e pe ooeoy peyay.

p epexoe aaee 1-xopaeceapaa peaoa cocooc x oaec -a oe yeooc aayeo aoa aoa N4 a ce +J ea aoo paaa R O N + HCl RNHCONHNHCOCH2Cl 14N O N H H 19e R1 = C6H11 (14, 19); pe-C4H9 (15, 20); pe-C5H11 (16, 21).

ooy a 1-xopae-4-aceapao (1416) poeae x ycox p e oo pacope apoaa ap, xo a cooa cxoe poy, coepae oee paa (pe-y pe-a), oope pocpaceo o apy yeoy aay.

3. oyee poox ecapo-1,2,4-paoo-3,Ha epe oye 1-aeee ecapo-1,2,4-pao-3,(2629) xop 1-ae(ee)-3,5-ocoecapo-1,2,4-pa (3032) oecae xopaexopa c 1-aee ceapaa ceapaoa H O N O H2NCONHNHRClCH2CONHCONHNHRN N H 22RClCH2COCl H RH2NCONHN C 26R3 O N O N ClN H C R3 R30e R = C6H5 (22, 26); n-CH3C6H4 (23, 27); n-O2NC6H4 (24, 28); C6H11 (25, 29); R = CH3, R4 = H (30); R = CH3, R4 = CH3 (31); R3 = C6H5, R4 = H (32).

Ce 1-xopaeceapao (22...24) poeae oo p apea peaoo acc o eepayp 6070C, a a ocooc aoa aoa N4 aeo e ocooc aoa N1 -a oc apoo py, oaae opae eoep eo. p o ppoa aecee apoaeco py a xo 1-ap-4-xopaeceapao e oaae + H2NCONHNHAr ClCH2COCl + HCl ClCH2CONHCONHNHAr 22 e Ar = C6H5 (22); n-CH3C6H4 (23); n-O2NC6H4 (24).

1-oec-4-xopaeceapa (25) oye ae p poee cea p eepaype 60C.

oyee xopaeceapa (2225) yaoc oa eee pa x ycox ee caoeoo cpee.

Bepoo -a oo, o ocooc aoa aoa N1 oeye aeeoo ceapaa e, e y aoa N4, pea a 1-ap-4xopaeceapao poeae opao ee, e 4-ap-1-xopaeceapao. 1-e-4-xopaeceapa oa 1eecapo-1,2,4-pao-3,5 ee pacope 1 pacopa apoaa ap eee 0,5 aca c xoo 76% H OO N + HCl ClCH2CONHCONHNHAr N 22N H Ar 26e Ar = C6H5 (22, 26); n-CH3C6H4 (23, 27); n-O2NC6H4 (24, 28).

Beee apoaecoe po aecee, oax ocooc aayeo aoa, cococye oe xoa eex pao, epooaeope py ca x xo. 1-n-Toecapo-1,2,4pao-3,5 (27) oye c xoo 79%, a xo 1-n-poeecapo-1,2,4-paoa-3,5 (28) cocae ceo 71% (a.3).

O O R4 R+ ClCH2COCl H2N C NHN C ClCH2CONH C NHN C R3 RH O N O N ClN+ H C R3 R30e R = CH3, R4 = H (30); R = CH3, R4 = CH3 (31); R = C6H5, R4 = H (32).

Ec aece cxox coee cooa ceapao aeo eoo, o poya pea xopaepoa c xop 1-ae(ee)-3,5-ocoecapo-1,2,4-pa (3032) Ce 3032 poo ee opx oec xopaexopa cooecyeo ceapaoa xopoope eee yx aco.

Taa o-xece coca 1-ap- 1-oececapo-1,2,4-paoo-3,5 xopo 1-ae-3,5-ocoecapo-1,2,4-pa Cl H H O O N O O N N N N H + N H RX Coepae B- Teepa -cep, ypa a- -cep, c-Ar(X) ocooo xo, Macc-cep, m/e coe. eeca, % % e, C 26 C6H5 98,6 76 189190 1465, 1595, 1685, 3400 220, 260 191, 114, 86, 27 n- CH3C6H4 98,4 79 177178 1455, 1585, 1680, 3400 230, 260 205, 91, 86, 840, 1430, 1500, 1585, 28 n- O2NC6H4 97,0 71 230 (pa.) 210, 255 236, 212, 166, 1690, 197, 154, 111, 42, 29 C6H11 98,2 78 151153 1470, 1590, 1690, 3380 30 CH3CH 99,3 66 129130 1440, 1680, 1740, 3230 - 31 (CH3)2C 99,4 67 142143 1430, 1675, 1740, 3220 - 32 C6H5CH 98,0 71 172173 1460, 1590, 1685, 3400 - oyex peyao cceoa pea xopaexopa c eaee aee ceapaa o, o ooee aecee oeye ceapaa cyeceo e a x peaoy cocooc: 4-aeee ceapa xopaepyc ee, e x pooe c aece ooe -1. Hae ax paao ae aoopo e a poeae pea xopaexopa c ceapaa.

o eoc a pa xopaeceapa oo pacoo cey p: 1-xopaeceapa > 1-a-4-xopaeceapa > 1-ap-4-xopaeceapa > 1-xopae-4-aceapa > 1-xopae-4-apceapa.

4. Ce epapo-1,2,4-paoo-3, Ha cceoaa pea oeca eaeeoo 4-aeeoo ceapaa c -eocoa RO N O R1NHCONHNHR5COCOOH + N R5 N H 33e R1=H, R5=CH3 (33); R1=H, R5=C6H5 (34); R1=H, R5= pe-C4H9 (35);

R1=H, R5=C4H3 (36); R1= pe-C4H9, R5=CH3 (37); R1= pe-C4H9, R5= C6H5 (38).

Ce poee ee opx oec peaeo pacope poca a (2% o). Be poeyoe poy e yaoc, oope, epoo, yc oe opaoa. Bcoy x peaoy cocooc oo oc ae oo c, cococye epepacpeee epoo ooc oe ocooc aoa aoa N4 ceapaoa.

Ce a ocoe eaeeoo ceapaa poea eo c co xoo eex pao. Hae aecee oeye ceapaa x ppoa cyeceo e a poeae pea ooeca. Ta, apaeee pa oy e yaoc. 4-Apooe 1,2,4-pao oye c xoo e e 70% (a. 4). Bepoo, o cyae oe paa pe-y pocpaceo apye yeoy aay aoo N4, xo oae eo yeooc. p cpae xoo epapo-1,2,4-paoo-3,5 (37, 38, a. 4) ecapo-1,2,4paoo-3,5 (2629, a. 3), o, o epe oyac c xoo e e 70%, a xo opx cyeceo e. poe oo, ce pao 37, 38 poo pcyc poca a eee pex aco, coee 2629 oya cpee 1. apoaa ap eee 0,5 aca. B epo cyae, epoo, aaac ecoo eaopx aopo: a ocyecec peyae yeoo aa eee oco aoo aoa N4; aaa apocoo yepoa pocpaceo apyea; a peyae oee oey o epoaec eee oa, e p oee xopooopoa.

Apoae 6-ooaeex 2,3,4,5-epapo-1,2,4-paoo-3,5 a cepoa x 3,6-aeee pooe COCHH O N O O N O (CH3CO)2O CH3COOH + + N N R5 N H R5 N H 3336 39, COC6HO N O C6H5COCl + HCl + N R5 N H 39, e R5 = CH3 (33, 37, 39, 40); C6H5 (34, 38, 43); pe-C4H9 (35, 41);

C4H3OCH2 (36, 42) 5. cceoae ooeco aoc poox ecepx pao eco, o pooe 1,2,4-pao po coy ecy aoc, aoee epec eeca a peyop poca pa pace. Oao a poeee cceoa o apaeoy c- Taa o-xece coca 6-oo- 4,6-aeex 2,3,4,5-epapo-1,2,4-paoo-3,R O O N N R N H Coepae Teepaypa Թ Bxo, R3 R1 ocooo ae, -cep, c-1 cep, Macc-cep, m/e coe. % eeca, % C 33 CH3 H 98,1 92 258 (pa.) 1550, 1690, 3200 221 127, 69, 55, 44, 34 C6H5 H 96,4 90 280 (pa.) 1600, 1690, 3210 254 189, 145, 117, 35 Tpe-C4H9 H 99,0 95 172173 1590, 1700, 3250 253 169, 97, 57, 36 C4H3OCH2 H 97,3 92 192194 1580, 1675, 3200 240 193, 121, 58, 37 CH3 Tpe-C4H9 97,2 70 252253 1550, 1680, 3200 244 183, 130, 58, 38 C6H5 Tpe-C4H9 98,1 72 260261 1600, 1680, 3250 248 245, 130, 117, 39 CH3 CH3CO 98,1 68 234235 - - 40 CH3 C6H5CO 98,2 57 241242 - - 41 pe-C4H9 CH3CO 98,4 64 183184 - - 42 C4H3OCH2 C6H5CO 98,0 62 178179 - - 43 C6H5 C6H5CO 98,0 66 276277 - - ey coee 1,2,4-paooo pa. ooy oyee peya cooa a p poee pooceco oe pocpeypye aoc oaa ox coee pa ecapo-1,2,4-paoo-3,5 -3,6. poo aoc, a ae oppoae ceao oe, poo c cooae oepo cce SARD.

pooa pocpeypye aoc cooa e oe M M2. Moe M1 opepoaa a oee ec, oop opaae pao poee pocpeypye aoc, eaco o a ec.

Peya pooceco oe oaa (oe M1), o a ce 11 coee, xo pa aoc pae o ocaoo xopoo paec. Haoee a ec coee (a. 5).

Taa Coooee peyao pooa o y oe M1 M ax cepea poo o ae cHaae coe. M1 M2 epea 17. 4-eecapo-1,2,4-pao-3,6 A A 26. 1-eecapo-1,2,4-pao-3,5 A A Ao + + 1--Hpoeecapo-1,2,4-pa28. A A o-3,Xop 1-opoe-3,5-ocoeca31. A A Ao + + + po-1,2,4-pa Xop 1-e-3,5-ocoecapo30. A B 1,2,4-pa Xop 1-ee-3,5-ocoeca32. A B Ao + + + po-1,2,4-pa ocoy o oe M1 ec a pocpeypyy aoc e opepoa, a ae epec peca opecyop, a coppoaa ceaa oe M2 pooa opecypye aoc. oaa ecpyex coee epe (17, 26, 28, 31) oaa coy opecypyy aoc (a. 5).

Bce oaa coee ca aece peyopo poca pa pace ooeco oee HT. oyee peya ceecy o ooeo oec cex coee a poc pae pace.

Bco ypoe aoc po p coee (26, 31, 32), x oee e xop 1-poe- 1-ee-3,6-ocoecapo-1,2,4-pa (31, 32). o pooy oo pae c coeee 31 axoc ae pooe 17 28, oope o a ooecoo cepea e oaa cooeceoo ypo aoc. B o e pe xop 1-ee-3,5-ocoecapo-1,2,4-pa (30) p ooeco cepee po coy aoc, o o peyaa pooa e ee (o oe M2). o-oy, ceoao ca ae coee oopo c pacpe cepo oeo oec.

Ceye oe, o peya pooa ae cepea coacyc. Aoc eex pex coee, epoo, caa c eace apoo, o aoo oopoa p eepoaoe eeoo pyo, coeeo c eepoaoo. pa peaeo aopa, xapaepye ae py, pcycy ax coeex.

oyex peyao o, o ca e peapao ec xop 1-opoe-3,5-ocoecapo-1,2,4-pa. ooy a papaoa cxoe ae paa exooeca cxea a oyee yaaoo poya.

BBO 1. Bepe poee cceaece cceoa pea xopaexopa c eaee 1-, 4-aee ceapaa. caoeo, o:

a) aoece eaeeoo ceapaa c xopaexopo po opaoa e ocaoo epaype ecapo-1,2,4paoa-3,6 c xoo 86% (ooe coooee cxox peaeo 1:1,5; pacope ea ycyca coa);

) p oeca 4-aeex ceapao c xopaexopo oyac paee e ece 4-apecapo-1,2,4-pao-3,6 c xoo 58-61% 4-aecapo-1,2,4-pao-3,6 c xoo 72-74%;

) poya pea 1-aeex ceapao c xopaexopo c oe coee ecapo-1,2,4-pao-3,5 (xoo 71-79%);

) p aoec ceapaoo aaecx aeo eoo c xopaexopo (100-105C, xopoop, opoe coooee cxox peaeo) opayc paee e ocae xop 1-a-e-3,5ocaecapo-1,2,4-pa c xoo 66-71%.

2. oaao, o aaec ceya aooepoc ee peaoo cocooc ceapao peax xopaepoa: 1apceapa < 4-aceapa < ceapa < 4-apceapa.

p a xopaeceapao aaec ceya aooepoc ee peaoo cocooc: 1-xopaeceapa > 1-a-4-xopaeceapa > 1-ap-4-xopaeceapa > 1xopae-4-aceapa > 1-xopae 4-apceapa.

3. Bepe cceoao aoece eaeeoo aeeoo aoyao c xopaexopo:

a) aoece eaeeoo aoyaa c xopaexopo (opoe coooee peaeo, pacope ea ycyca coa) oye 3-ao 3-xopaeao-1,2,5,6-epapo-1,2,4pao-6 c xoo 75 78%;

) aoece yapaoo c xopaexopo oye paee e ocae 2-apepaoaoo-4 c xoo 90-92% 2-aepaoaoo-4 c xoo 84-85%.

4. Ocyece ce 4,6-aeex 2,3,4,5-epapo-1,2,4-paoo-3,5:

a) aoece eoco c 4-pe-yceapao (100110C, opoe coooee peaeo, 2% o poca a) oye 4,6-a(ap)-2,3,4,5-epapo-1,2,4-pao-3,5 c xoo 70-72%;

) aoece eoco c eaee ceapao (100110C, opoe coooee peaeo, 2% o poca a) oye 6-a(ap)-2,3,4,5-epapo-1,2,4-pao-3,5 c xoo > 90%.

Apoae ocex ycyc apo xopapa co (oe coooe peaeo 1:1,1) oye 4-a-6-a(ap)- 2,3,4,5epapo-1,2,4-pao-3,5 c xoo 57-68%.

5. o peyaa oepoo pooa, oope coa c peyaa poeex ooecx ca, ca epce peyopo poca pa pace ec xop 1-opoe-3,5ocoecapo-1,2,4-pa.

6. B peyae poeex cceoa oyeo 55 coee, oopx 49 e oca epaype.

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