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
收藏
页码：649 / 652
页数：4
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