Synthesis of N-substituted pyrrole and tetrahydroindole derivatives from alkenyl β-dicarbonyl compounds

被引：50

作者：

Ferraz, HMC ^{[1
]}

Pereira, FLC ^{[1
]}

Leite, FS ^{[1
]}

Nunes, MRS ^{[1
]}

Payret-Arrúa, ME ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05599970 Sao Paulo, Brazil

来源：

TETRAHEDRON | 1999年 / 55卷 / 36期

基金：

巴西圣保罗研究基金会;

关键词：

nitrogen heterocycles; enamino esters; cyclization; elimination reactions;

D O I：

10.1016/S0040-4020(99)00625-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodocyclization of a series of alknyl-substituted beta-enamino esters and ketones, followed by base-promoted dehydroiodination, led to the formation of the corresponding pyrrole or tetrahydroindole derivatives. In the absence of base, the iodo-beta-enamino esters 5 and 7 underwent spontaneous aromatization after dehydroiodination, furnishing the 4, 5, 6, 7-N-substituted-tetrahydroindoles 19 and 20. All the elimination reactions proceeded smoothly, in yields ranging from 71% to 99%. Starting from the beta-allyl-dimedone 21, it was possible to prepare the oxotetrahydroindole 24, in moderate overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：10915 / 10924

页数：10

共 26 条

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