New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence

被引：52

作者：

He, Ping ^{[1
]}

Wu, Jing ^{[1
]}

Nie, Yi-Bo ^{[1
]}

Ding, Ming-Wu ^{[1
]}

机构：

[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

来源：

TETRAHEDRON | 2009年 / 65卷 / 41期

基金：

中国国家自然科学基金;

关键词：

AZA-WITTIG REACTION; CONSTRUCTION; DERIVATIVES; ROUTE;

D O I：

10.1016/j.tet.2009.08.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.

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页码：8563 / 8570

页数：8

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