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
收藏
页码：6351 / 6358
页数：8
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