SYNTHESIS OF PYRROLOQUINOLINES FROM SUBSTITUTED 6-AMINOINDOLES AND OXALOACETIC ESTER

被引：1
|
作者：
Yamashkin, S. A. [1 ]
Zhukova, N. V. [1 ]
Romanova, I. S. [1 ]
机构：
[1] M E Evsevyev Mordovinian State Pedag Inst, Saransk 430007, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2008年 / 44卷 / 07期
关键词：
substituted; 6-aminoindoles; pyrrolo[2,3-f]quinolines; pyrrolo[3,2-g]quinolines; oxaloacetic ester;
D O I：
10.1007/s10593-008-0111-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280 degrees C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.
引用
收藏
页码：793 / 801
页数：9
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