Bromodimethylsulfonium bromide (BDMS)-mediated Lossen rearrangement: synthesis of unsymmetrical ureas

被引：30
|
作者：
Yadav, Deepak K. [2 ]
Yadav, Arvind K. [1 ]
Srivastava, Vishnu P. [1 ]
Watal, Geeta [2 ]
Yadav, Lal Dhar S. [1 ]
机构：
[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
[2] Univ Allahabad, Dept Chem, Med Res Lab, Alternat Therapeut Unit,Drug Dev Div, Allahabad 211002, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 23期
关键词：
Bromodimethylsulfonium bromide (BDMS); Lossen rearrangement; Hydroxamic acids; Isocyanates; Unsymmetrical ureas; ONE-POT SYNTHESIS; (BROMODIMETHYL)SULFONIUM BROMIDE; REAGENT; DERIVATIVES; INHIBITORS; CHEMISTRY; AMINES; ACIDS;
D O I：
10.1016/j.tetlet.2012.03.129
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bromodimethylsulfonium bromide (BDMS) was found to be a very efficient reagent for Lossen rearrangement of hydroxamic acids to the corresponding isocyanates which were subsequently trapped in situ with various amines to afford unsymmetrical ureas in good to excellent yields (64-89%). The protocol is experimentally simple, mild, and represents valuable alternative to the existing methods for in situ activation of hydroxamic acids promoting Lossen rearrangement. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2890 / 2893
页数：4
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