Synthesis of 1-substituted tetrazoles via the acid-catalyzed [3+2] cycloaddition between isocyanides and trimethylsilyl azide

被引：120

作者：

Jin, TN ^{[1
]}

Kamijo, S ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 51期

关键词：

tetrazole; 1-substituted tetrazole [3+2] cycloaddition; isocyanide; trimethylsilyl azide; acid-catalyzed reaction; hydrazoic acid;

D O I：

10.1016/j.tetlet.2004.10.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

1-Substituted tetrazoles were synthesized via the [3+2] cycloaddition between isocyanicles and trimethylsilyl azide in the presence of an acid catalyst and MeOH. Various I-substituted tetrazoles were obtained in good to high yields. The reaction probably proceeds through the in situ formation of hydrazoic acid, followed by a successive [3+2] cycloaddition with the isocyanide activated by an acid. (C) 2004 Published by Elsevier Ltd.

引用

页码：9435 / 9437

页数：3

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