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Ha paax pyoc MATOBA MPA AMEBHA CHTE, CBOCTBA BOMOHE OACT PMEHEH HECMMETPHX TPAHOHOB 02.00.13 Heex Aopeepa a cocae yeo cee aaa xecx ay a-2002 Paoa oea a aepe pao x coo ocyapceoo eoo execoo yepcea.

Hay pyooe: oop execx ay, poeccop B.X. XAMAEB Oae ooe: oop xecx ay, poeccop C.C. OTC aa execx ay c..c. A.M. OH Beya opaa: apc ocyapce ec yepce aa cococ 20 cep 2002 . aco a acea ccepaooo coea 212.289.01 p co ocyapceo eo execo yepcee (HT) o apecy: 450062, . a, y.

ocoao, 1.

C ccepae oo oaoc oee HT.

Aopeepa paoca ayca 2002.

e cepeap ccepaooo coea, poeccop A.M. CPH OA XAPATEPCTA PAOT Ayaoc e. pooe ecepx pao oaa po cepo paec ex coc c o epcex acco eepoecx coee. O peoe aece epo peyopo poca pace, ceo yo, eapcex eepapx eec, a ae caaopo-aocao oepo. Oco epec peca 1,2,4-pao, oope, cy o ec epaype cee, ye eocaoo. poe oo, ece oooc cea x eepoecx coee opae ocyoc cxox coee, oocaoc poecca xoo eex poyo. ooy ayao poeo ec papaoa eoo cea yee ecx, xecx ooecx coc oco- ocopoox 1,2,4-pao c cooae aece cxox eec oee ocyx peaoococox coo xopaexopa, ceapao aoyaa.

Paoa oea cooec c ayo-execo popao Mopaoa P Haye cceoa ce o oac x xecx poyo (pa Mopaoa P o 08.02.2000 ., 391).

e pao. Papaoa eoo apaeoo cea 1,2,4ecapopaoo-3,5 -3,6, ee cpe x coee, oaax ec coca.

oce ocaeo e peac ceye aa:

1. Aa ooee epaypx ax o eoax cea oox oacx pee ppoax 1,2,4-paoo-3,5 -3,6 1,2,4-paoo-6.

2. Papaoa eoo oye ppoax 1,2,4-paoo 1,2,4-paoo.

3. Cceaecoe yee pea oeca xopaexopa c ceapaa.

4. Opeeee pocpeypye aoc ox coee 1,2,4paooo pa papaoa cxox ax a pooco epceoo eeca.

Haya oa. Papaoa opae eo cea poox 1,2,4-paoo-6 1,2,4-paoo-3,5 3,6, aaec oeca xopaexopa c eaee aee ceapaa aoyao.

Bepe cceoao aoece xopaexopa c eaee aee aoyaa, poee opaoa paee epaype e ocax 3-ao-1,2,5,6-epapo-1,2,4-paoo-6, aeex 2-paaooo-4.

Bepe cceoao aoece xopaexopa c eaee aee ceapaa c opaoae paee epaype e ocax ecapo-1,2,4-paoo-3,5 -3,6. caoeo, o a ocoe 1-aeex ceapao oyac 1-aeee ecapo-1,2,4pao-3,5, 1-aeex ceapaoo xop x pao.

ooeca 4-aeex ceapao c xopaexopo po 4-aee ecapo-1,2,4-paoa-3,6.

cceoa eo oye paee e ocax 3,6-aeex epapo-1,2,4-paoo-3,5 a ocoe -eoco ceapao.

Bepe poee oep poo ep cp ooeco aoc cepoax coee, peya oopx coa oo epcee poy.

paeca eoc pao. Papaoa o eo oye 1aeex ecapo-1,2,4-paoo-3,5 4-aeex ecapo1,2,4-paoo-3,6, aac oeca xopaexopa, eoc ocy eexec cpe, aeex eaeeoo ceapao.

Papaoa o epce peyop poca pa pace xop 1-opoe-3,5-ocoecapo-1,2,4-pa, oop poe epe ca peoe pox ca.

o peyaa oex cceoa papaoa yepe oo Coeo HT Pea exece yco aopaope eo a epe coee, oope o aao xecx peao.

Apoa pao. pecaee ccepa peya ooe a XII Meyapoo oepe o poocy pee xecx peao peaeo (7-9 cep 1999 ., . a); III V Meyapox ayo-execx oepex AC HT (7-10 ape 1999 ., 3-6 ape 2001 . a); VI Meyapoo ayo-execo oepe p Meyapoo ceapoao cae Cpoeco, apxeypa, oyaoe xoco - 2002 (17-19 ape 2002 ., . a); 17 epaoao coye Ce opaeco x (23-26 2001 ., . Ocop).

ya. o ee ccepa oyoao 7 cae, 2 eca oao.

Oe cpyypa pao. ccepaoa paoa oea a 155 c., coco ee, oopa epayp, 5 a, oo, cca epayp poe. Coep 22 a. Cco epayp ae 150 coo.

OCHOBHOE COEPAHE PAOT 1. Baoece xopaexopa c eaee aee aoyaa eco, o p oeca aoyaa c -eoa oyac aeee 3-ao-1,2,4-pa. p cooa aece apooo coee -eoco poya pea c 3aoepapo-1,2,4-pao-5. Ha cceoao aoece eaeeoo aeex aoyao c xopaexopo.

oeca xopaexopa c eaee aoyao poeae c eee ea. Ce ocyecec eo ycyco coe pcyc eooo aeaa ap. p opo coooe cxox peapyx eec opayec 3-ao-1,2,5,6-epapo-1,2,4pao-6 (1), p e xopaexopa (2 : 1 o) oe poyo ec 3-xopaeao-1,2,5,6-epapo-1,2,4-pao-6 (2) NH N N NH O N H H2NCNHNH2 + ClCH2COCl H NHCOCH2Cl N N O N H H p cee aopaa 1 peaoo acc eaeo oece ee xopaeaopa 2 (e oee 5%). o-xece coca pao 1 2 pee a.1.

Xopaepoae yapaoo, N1-aeex aoyao e coepax ao oopoa p aoe N1, po ooy accy coee aooa-4. eco, o o acc coee pecae paec epec a ooec ae eeca.

Taa o-xece coca aocoepax eepoo opya Haae Coepa- B- Teepa- -cep, Macccoe. e oco- xo, % ypa a- c-1 cep, oo ee- m/e e, C ca, % NHN 114, 84, 3-ao-1,2,5,6-epa- 1520, 1680, N 1. 98 75 105106 68, 42, po-1,2,4-pao-6 1710, O N H H NHCOCH2Cl N 3-xopaeao- 820, 1300, 191, 2. N -1,2,5,6-epapo- 97 78 145146 1515, 1680, 113, 83, O N H -1,2,4-pao-6 1720 78, H 830, 1385, 202, O N 2-eepa- 5. 98 90 1485, 1620, 113, 90, NHN CHC6Hoaoo-4 (pa.) NH 1710, 3365 O N 840, 1390, 232, 2-n-eocee- 6. NHN CHC6H4OCH3 97 92 1480, 1645, 113, 84, paoaoo-4 (pa.) NH 1710, 3375 O N 2- 1250, 1370, 154, CH7. opoepa- 97 84 144145 1475, 1630, 110, 81, NHN C NH CH oaoo-4 1715 O N 2- 1260, 1375, CH168, 8. NHN C opyepa- 97 85 152153 1480, 1630, 110, NH C2H oaoo-4 paopooe aooa-4 e oca epaype. Ha oyeo epe coee aoo pa.

Xopaepoae apoaecx poox aoyaa poeae eee epooeoo pee copooaec eae eee ea. Ce poo eo ycyco coe NCOCH2Cl NCOCH2Cl NH NH C C C H2N NHN C H2N NHN H2N NHN CHAr H2N NHN CHAr CHAr + ClCH2COCl CHAr + ClCH2COCl 3, O N O N NHN CHAr NHN CHAr NH 5, e Ar = C6H5; n-CH3OC6H5.

Cpoee 1-ap-4-xopaeyapaoo aeo 3, 4 epoao o acc-, - MP13C cepa. B -cepax ec ooc ooe xapaepe epo aopy (3400- 3460 c-1), o oepae peoey cpyypy c xopaeo pyo p o aoe. Cpoee oyex coee 3 4 ae oepeo a- NH e cao C O, CH2Cl NCNH cepax MP13C. Moeype acc, opeeee acc-cepoepec eoo, coa c eopeec.

oyee 1-ap-4-xopaeyapao eo yc p apea pe 2-apepaooaoo-4 (5 6) c xoo 84-92% (a. 1).

p epexoe o appoox aaee yapaoa yeooc aoa N4 opacae, epoo, ooy poeyoe poy xopaepoa yapaoo aaecx eoo 1-a4-xopaeyapao oaa coo peaoo cocooc yc oe opaoa oe poya pea c eocpeceo 2-aepaoaoo-4 (7, 8) NCOCH2Cl NH RR ClCH2COCl H2N C NHN C + 2 ] [H N C NHN C RRO N R NHN C NH R7, e R1 = CH3; R2 = CH3; C2H5.

oyee 2-ape(ae)paoaoo-4 (58) peca coo pcaece eeca, xopoo pacope o ox opaecx pacopex. x o-xece coca cepae xapaepc pee a. 1.

2. Ce 1-aeex ecapo-1,2,4-paoo-3,ooc acee 1,2,4-pa c y ocopya ooe 3 6 oye oecae eaeeoo N4-aeex ceapao c xopaexopo o ceye cxee:

H N O R1=H N O O N H R1NH C NHNH2 + ClCH2COCl H O R1=Ar, AlK R1NH C NHNHCOCH2Cl 10RN O N O N H H 17e R1= H (9); C6H5 (10, 17); n-CH3C6H4 (11, 19) ; n-CH3OC6H4 (12);

n-O2NC6H4(13); C6H11 (14, 19); pe-C4H9 (15, 20); pe-C5H11 (16, 21).

p xopaepoa eaeeoo ceapaa e poeyo poy e yaoc, oop, epoo, oe opaoa oepaec ypoeypo epepypoe, copooaec oeee xopooopoa opaoae ecapo-1,2,4-paoa-3,6 (9). ooee ocopy oeye ecapo-1,2,4-paoa-3,6 (9) oepae peooee o o, o poecc aaec c aoec oee ocooo aoa aoa N1 ceapaa c apo yepoo xopaexopa poeae epe ca opaoa 1-xopaexopa. p epexoe 4-aee ceapaa a yaoc e epoa poeyoe 1-xopae-4-ap(a)ceapa. Xopaepoae 4-apce-apao a oyeo epe poya HCl ArNHCONHNHCOCH2C l ClCH2COCl + ArNHCONHNH+ 10e Ar = C6H5 (10); n-CH3C6H4 (11); n-CH3OC6H4 (12); n-O2NC6H4 (13).

Pea oeca oe ocyecea eo ycyco coe e pacope c cooae a xopaexopa. B epo cyae xo 1-xopae-4-apceapao e e 67%. p poee cea e pacope xo 10 aae c 72% o 64%, p eo ee eoxoo poo oopy epepcaa ooo cpa. p yee pee pea (oee 30 .) xo poyo pea ae aae, .. aaec opaoae coooooo eeca, oopoe epoa e yaoc. Ta, xo 10 cocae ceo 57% p yee pee pea o ooo aca.

Bxo 1-xopae-4-apce-apao (1013) ac o ppo aecee apoaeco pe. Hae epoooopx py cococye oe xoa appoox ceapaa o ooe eaeeoy po 4-eceapay, a eee epooaeopx py, aoopo, oe xoa poyo pea. Bxo 10 cocae 72%, xo 11, 12 e e 84%, a 1-xopae-4-n-poeceapa (13) oye c xoo 67%.

Beee ao py oeyy ceapaa po oe ocooc aoa aoa N1, ooy xopaepoae 4-aceapao poeae oee ao, e appoox R1NHCONHNHCOCHCl+ HCl R1NHCONHNH+ ClCH2COCl 14e R1 = C6H11 (14); pe-C4H9 (15); pe-C5H11 (16).

Oao xo 1-xopae-4-aceapao (15, 16) e, e y appoox. B ao cyae aoe poeae pea xopaepoa aceapao po acoy ocoe poyo pea cece eo, ce xoa 15 16. poeee cea xopoope ooe ye xo 1-xopae-4-aceapao a 10-15%. oyee 1-xopae-4-ap(a)ceapa oepa a eee pa.

ppoa aece y aoa N4 e a peaoy cocooc xopaepoax ceapao y oc pacooe eo aayey aoy aoa. a 1-xopae-4-apceapao apyea -a pcyc apoaecoo paaa ooe -4, oaeo yeooc aayeo aoa N4. x a yaoc poec ecx ycox.

oyeo a 4-apecapo-1,2,4-paoa-3,6 (1718) e ee cooecyx 1-xopae-4-apce-apao eopae (MA) (a. 2) Taa o-xece coca 4-ap(a)ecapo-1,2,4-paoo-3,R O N N O N H H Coepa- Teepa e oco- Bxo, ypa -cep, R1 -cep, c-1 Macc-cep, m/e aecoe. oo ee- % ca, % , C 9 H 98,4 86 190191 1460, 1550, 1660, 3320 230 115, 87, 1440, 1500, 1580, 1630, 17 C6H5 98,2 58 227228 225, 260 191, 163, 86, 1445, 1510, 1590, 1630, 18 n- CH3C6H4 98,0 61 215216 230, 250 205, 177, 19 C6H11 98,2 74 169170 1470, 1560, 1670, 3310 240 197, 169, 86, 20 pe-C4H9 98,0 72 200201 1470, 1555, 1665, 3360 230, 250 171, 143, 86, 21 pe-C5H11 98,4 74 145146 1475, 1560, 1680, 3340 235, 250 185, 157, 86, Ar O N + HCl ArNHCONHNHCOCH2Cl 10, N O N H H 17, e Ar = C6H5 (10, 17); n-CH3C6H4 (11, 18).

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