A Strecker approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates

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• 作者：Ken Cheng ; Andrew McClory ; ^{mcclory.andrew@gene.com" class="auth_mail" title="E-mail the corresponding author} ; Whitney Walker ; Jie Xu ; Haiming Zhang ; Remy Angelaud ; Francis Gosselin
• 关键词：Thiazole ; Strecker ; Convergent ; Thioamide ; Cyanide
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：20 April 2016
• 年：2016
• 卷：57
• 期：16
• 页码：1736-1738
• 全文大小：2292 K

文摘

A general approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates is reported herein. Both aliphatic and aromatic thioamides undergo 1,2-addition to ethyl glyoxylate to give hemiaminals which, when treated with acetyl chloride, undergo elimination to the corresponding imines. Upon exposure to aqueous sodium cyanide the imines undergo a Strecker addition–cyclization reaction to provide the target heterocycles in modest to good yields over the 3-step process.