A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCI/NaOH
A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCI/NaOH
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DOI：
10.1016/j.tet.2004.08.031
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发表时间：
2004-10-25
期刊：
影响因子：
2.1
通讯作者：
Beckmann, HSG
中科院分区：
文献类型：
--
作者：
Heinelt, U;Schultheis, D;Beckmann, HSG
对甲苯磺酰氯（TsCl）/NaOH作为试剂组合用于N-（2-羟乙基）硫脲合成2-氨基-氧杂-或2-氨基-噻唑烷，但其在杂环合成中的应用尚未见报道。本文介绍了一系列不同取代基和环大小的2-氨基取代的1-氮杂3-（氮杂、氧代或硫代）杂环化合物的简便、有效的合成方法。聚合物支撑的TsCl的应用促进了后处理，并使得反应条件非常适合于并行或机器人合成。(C)2004爱思唯尔有限公司保留所有权利。
p-Toluenesulfonyl chloride (TsCl)/NaOH has been introduced as reagent combination for the synthesis of 2-amino-oxa- or 2-amino-thiazolidines from N-(2-hydroxyethyl)-thioureas, but its general application in heterocycle synthesis has not been investigated. In this paper the convenient and efficient synthesis of a variety of 2-amino-substituted 1-aza 3-(aza, oxo or thio) heterocycles of different substitution and ring sizes is described. The application of polymer-supported TsCl facilitates work-up and renders the reaction conditions very suitable for parallel or robot synthesis. (C) 2004 Elsevier Ltd. All rights reserved.