An efficient conjugate hydrothiocyanation of chalcones with a task-specific ionic liquid

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• 作者：Lal Dhar S. Yadav ; Rajesh Patel ; Vijai K. Rai ; Vishnu P. Srivastava
• 关键词：Hydrothiocyanation ; Conjugate addition ; Chalcones ; Ionic liquids ; Thiocyanates ; 1 ; 3-Thiazines
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：29 October 2007
• 卷：48
• 期：44
• 页码：7793-7795
• 文件大小：118 K

摘要

A new and efficient method of conjugate hydrothiocyanation of chalcones along with the preparation of a probe for demonstrating the utility of the resulting β-thiocyanato ketones in heterocyclic synthesis is reported. Chalcones undergo an efficient conjugate hydrothiocyanation with the task-specific ionic liquid (TSIL), 1-n-butyl-3-methylimidazolium thiocyanate ([bmim]SCN) followed by reaction with AcONH₄ or an amine to afford chemically and pharmaceutically interesting 2-amino-1,3-thiazines at room temperature in a one-pot procedure. After isolation of the product, the ionic liquid [bmim]OH could be used for the synthesis of [bmim]SCN, thus allowing recycling of the TSIL for further use.