Copper-catalyzed tandem reactions of 2-halobenzenamines with isothiocyanates under ligand- and base-free conditions

被引：94

作者：

Guo, Yan-Jin ^{[1
]}

Tang, Ri-Yuan ^{[1
]}

Zhong, Ping ^{[1
]}

Li, Jin-Heng ^{[1
,2
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325035, Peoples R China

[2] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Copper; Tandem reaction; 2-Halobenzenamine; Isothiocyanate; 2-Aminobenzothiazole; CROSS-COUPLING REACTIONS; S BOND FORMATION; INTRAMOLECULAR CYCLIZATION; ARYL CHLORIDES; EFFICIENT; BENZOTHIAZOLES; SYSTEM; THIOLS; DERIVATIVES; IODIDES;

D O I：

10.1016/j.tetlet.2009.11.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ligand-free copper-catalyzed reaction of 2-halobenzenamines with isothiocyanates has been developed for the synthesis of 2-aminobenzothiazoles. In the presence of CuBr and TBAB (tetra-n-butyl ammonium bromide, additive), a variety of 2-halobenzenamines underwent the reaction with isothiocyanates at 40 degrees C, affording 2-aminobenzothiazoles in moderate to excellent yields. It is noteworthy that the reaction is conducted under mild, relatively low catalyst loading, and ligand- and base-free conditions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：649 / 652

页数：4

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