A convenient synthetic route to 2-aryl-N-tosylazetidines and their ZnX2 (X = I, OTf) mediated regioselective nucleophilic ring opening reactions:: synthesis of γ-iodoamines and tetrahydropyrimidines

被引：48

作者：

Ghorai, Manas K. ^{[1
]}

Das, Kalpataru ^{[1
]}

Kumar, Amit ^{[1
]}

Das, Animesh ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 30期

关键词：

2-aryl-N-tosylazetidine; 4+2]cycloaddition; ZnX2; (X; I; OTf); gamma-iodoamines; tetrahydropyrimidine;

D O I：

10.1016/j.tetlet.2006.05.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and convenient synthetic route to various 2-aryl-N-tosylazetidines has been described. Their ZnX2 (X = I, OTf) mediated nucleophilic ring opening with halides and [4+2] cycloaddition reactions with various nitriles have been achieved to afford gamma-iodoamines and substituted tetrahydropyrimidines, respectively, in good to excellent yields. A mechanism for the cycloaddition reaction is proposed. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5393 / 5397

页数：5

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