A new methodology for the preparation of 2-cyanopyrroles and synthesis of porphobilinogen

被引:20
作者
Adamczyk, M
Reddy, RE
机构
[1] Div. Organ. Chem. Res. (9NM, AP20), Diagnostic Division, Abbott Laboratories, Abbott Park, IL 60064-3500
关键词
D O I
10.1016/0040-4020(96)00941-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Condensation of alpha-acetoxynitro compounds 4a-f with isocyanoacetonitrile (5) using DBU in THF afforded 2-cyono-3,4-substituted pyrroles 6a-f, in good yield. Porphobilinogen (PBG, 12), the key building block for the preparation of tetrapyrrolic natural products, was synthesized from 2-cyano-3,4-substituted pyrrole 6f, in four steps. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:14689 / 14700
页数:12
相关论文
共 94 条
[1]   A CONVENIENT AND VERSATILE SYNTHESIS OF PORPHOBILINOGEN [J].
ADAMCZYK, M ;
REDDY, RE .
TETRAHEDRON LETTERS, 1995, 36 (50) :9121-9124
[2]   A CONVENIENT SYNTHESIS OF 2-CYANOPYRROLES FROM ISOCYANOACETONITRILE [J].
ADAMCZYK, M ;
REDDY, RE .
TETRAHEDRON LETTERS, 1995, 36 (44) :7983-7986
[3]  
AKTHAR M, 1979, COMPREHENSIVE ORGANI, V5, P1121
[4]   THE REACTION OF BETA-AMINOENONES WITH ALPHA-AMINO DERIVATIVES - SYNTHESIS OF 2-FUNCTIONALIZED PYRROLES [J].
ALBEROLA, A ;
ANDRES, JM ;
GONZALEZ, A ;
PEDROSA, R ;
VICENTE, M .
HETEROCYCLES, 1990, 31 (06) :1049-1058
[5]  
ANDERSON PM, 1979, J BIOL CHEM, V254, P6924
[6]   PYRROLES RELATED TO PORPHOBILINOGEN [J].
ARSENAULT, G ;
MACDONALD, SF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1961, 39 (10) :2043-&
[7]  
BACKE F, 1970, LIEBIGS ANN CHEM, V735, P27
[8]  
BARTON DHR, 1990, TETRAHEDRON, V46, P7587
[9]   A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].
BARTON, DHR ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100
[10]  
BATTERSBY AR, 1982, J CHEM SOC PERK T 1, P2427, DOI 10.1039/p19820002427