CYCLODEHYDRATION OF 4-[(CARBOXYMETHYL)AMINO]PYRIDIN-2-ONES - A NEW, EFFICIENT SYNTHESIS OF PYRROLO[3,2-C]PYRIDIN-4-ONES AND PYRIDO[3,4-B]PYRROLIZIDIN-1-ONES

被引：8

作者：

EDSTROM, ED

YU, T

机构：

[1] Department of Chemistry and Biochemistry, Utah State University Logan

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 38期

关键词：

D O I：

10.1016/0040-4039(94)88205-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes an efficient new route for the synthesis of pyrrolo[3,2-c]pyridin-2-ones and pyrido[3,4- b]pyrrolizidin-1-ones starting from 4-chloro-N-benzyl-2(1H)-pyridinone and amino acid salts. Intermediate 4-[(carboxymethyl)amino]pyridin-2-ones undergo an acylative cylclodehydration reaction to afford 3-acetoxy pyrroles. These intermediates are then converted into J-oxytriflate derivatives in high yield using a new one-step method. These compounds undergo palladium catalyzed methoxycarbonylation.

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收藏

页码：6985 / 6988

页数：4

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