Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure

被引：60

作者：

Gámez-Montaño, R ^{[1
]}

González-Zamora, E ^{[1
]}

Potier, P ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 32期

关键词：

multi-component reaction; isonitrile; polyheterocycle; pyrrolopyridine; high throughput synthesis;

D O I：

10.1016/S0040-4020(02)00634-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine (3), an aldehyde (4) and an alpha-isocyanoacetamide (5) in methanol at room temperature provides an efficient access to oxa-bridged tricycle (1) as a single diastereoisomer. In this one-pot process, one C-N, one C-O and three C-C bonds are formed with concomitant creation of five asymmetric centers. While isolable, the oxa-bridged tricycles (1) can be cleanly in-situ fragmented to pyrrolopyridines (2) under acidic conditions (trifluoroacetic acid, -78degreesC), providing thus an unusual work-up derived structural diversity. The operational simplicity and excellent chemical yield make these novel heterocycle syntheses valuable in diversity-oriented high throughput synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6351 / 6358

页数：8

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