An effective synthesis of N-substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones that uses 1,2-benzisothiazolin-3-one as a leaving group

被引：28
|
作者：
Shimizu, M
Sugano, Y
Konakahara, T
Gama, Y
Shibuya, I
机构：
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 6058565, Japan
[2] Sci Univ Tokyo, Fac Sci & Technol, Dept Ind Chem, Chiba 2788510, Japan
来源：
TETRAHEDRON | 2002年 / 58卷 / 19期
关键词：
amines; benzisothiazoles; substitution; sulfenic acids and derivatives;
D O I：
10.1016/S0040-4020(02)00329-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Substituted 2-sulfenamoylbenzoates and 1,2-benzisothiazolin-3-ones were effectively synthesized by the substitution reaction between S-[2-(3-oxo-1,2-benzisothiazolinyl)]-2-mercaptobenzoates (2) and primary amines. The substitution reaction occurred on the sulfur atom of the 2-sulfenamoyl group of 2, and 1,2-benzisothiazolin-3-one behaved as a leaving group. The eliminated 1,2-benzisothiazolin-3-one could be reused as a starting material for the synthesis of 2, N,N-Disubstituted 2-sulfenamoylbenzoates were prepared by the reaction of 2 with secondary amines. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3779 / 3783
页数：5
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