CONJUGATED AZOALKENES .14. SYNTHESIS OF NEW 1-AMINO-PYRROLE AND 1,2-DIAMINO-PYRROLE DERIVATIVES BY REACTION OF SOME CONJUGATED AZOALKENES WITH ACTIVATED METHYLENE-COMPOUNDS RCH2AC AND RCH2CN (R = ARYL, HETEROARYL)

被引:17
作者
ATTANASI, OA
LIAO, ZY
MCKILLOP, A
SANTEUSANIO, S
SERRAZANETTI, F
机构
[1] BEIJING INST TECHNOL,DEPT CHEM ENGN,BEIJING 100081,PEOPLES R CHINA
[2] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 03期
关键词
D O I
10.1039/p19930000315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Amino- and 1,2-diamino-pyrrole derivatives are obtained in high yield by reaction of conjugated azoalkenes with ketones and cyanides containing methylene groups further activated by a 4-nitrophenyl, 2-fluorophenyl, benzothiazol-2-yl or benzimidazol-2-yl group. In some cases the heterocycles can be prepared in a one flask procedure, while in others a two step sequence is required, namely, formation of the 1,4-conjugate adduct and then cyclization. Reaction of 2,4-dichloro- and 2,3,6-trichlorophenylacetonitrile with the azoalkenes gave the 1,4-conjugate adducts, but these could not be successfully cyclized.
引用
收藏
页码:315 / 320
页数:6
相关论文
共 10 条
[1]  
ATTANASI O, 1984, SYNTHESIS-STUTTGART, P671
[2]  
ATTANASI O, 1984, SYNTHESIS-STUTTGART, P873
[3]  
Attanasi O. A., 1986, ORG PREP PROCED INT, V18, P299
[4]   CONJUGATED AZOALKENES .12. SYNTHESIS OF NEW 1-AMINO-3-CYANOPYRROLE, 1,2-DIAMINOPYRROLE AND PYRROLO[2,3-B]PYRROLE DERIVATIVES BY REACTION OF SOME CONJUGATED AZOALKENES WITH ACTIVATED NITRILES [J].
ATTANASI, OA ;
DECRESCENTINI, L ;
SANTEUSANIO, S ;
SERRAZANETTI, F ;
MCKILLOP, A ;
LIAO, ZY .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (08) :1009-1014
[5]   CONJUGATED AZOALKENES .8. REACTION OF SOME CONJUGATED AZOALKENES WITH ACTIVATED NITRILES - SYNTHESIS OF NEW PYRROLO[2,3-B]PYRROLES AND 1,2-DIAMINOPYRROLES - X-RAY MOLECULAR-STRUCTURE OF DIETHYL 6-AMINO-1,6-BIS-(TERT-BUTOXYCARBONYLAMINO)-3A-CYANO-2,5-DIMETHYL-1,3A,6,6A-TETRAHYDROPYRROLO-[2,3-B]PYRROLE-3,4-DICARBOXYLATE [J].
ATTANASI, OA ;
SANTEUSANIO, S ;
SERRAZANETTI, F ;
FORESTI, E ;
MCKILLOP, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1669-1675
[6]   CONJUGATED AZOALKENES .9. NEW 1-AMINO-4-TRIPHENYLPHOSPHORANYLIDENE-5-OXO-2-PYRROLINES OR ALPHA,BETA-UNSATURATED HYDRAZONES BY REACTION OF AZOALKENES WITH CARBOALKOXYMETHYLENE TRIPHENYLPHOSPHORANE [J].
ATTANASI, OA ;
FILIPPONE, P ;
MEI, A ;
BONGINI, A ;
FORESTI, E .
TETRAHEDRON, 1990, 46 (16) :5685-5696
[7]   CONJUGATED AZOALKENES .13. FACILE AND HIGH-YIELD SYNTHESIS OF NEW 1-AMINO-3-CYANO-2,3-DIHYDROPYRROL-2-OLS AND 1-AMINO-3-CYANO-1H-PYRROL-2(3H)-ONES [J].
ATTANASI, OA ;
DECRESCENTINI, L ;
MCKILLOP, A ;
SANTEUSANIO, S ;
SERRAZANETTI, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (22) :3099-3102
[8]  
ATTANASI OA, 1989, GAZZ CHIM ITAL, V119, P631
[9]   EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .33. 2-HYDROXY-4-PYRROLINES AS STABLE INTERMEDIATES IN THE SYNTHESIS OF 1-AMINOPYRROLE DERIVATIVES [J].
ATTANASI, OA ;
GROSSI, M ;
SERRAZANETTI, F ;
FORESTI, E .
TETRAHEDRON, 1987, 43 (18) :4249-4256
[10]   DIVERSITY OF REACTION OF AZOALKENES IN CYCLOADDITIONS [J].
FERGUSON, G ;
LOUGH, AJ ;
MACKAY, D ;
WEERATUNGA, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3361-3369