Concise Assembly of Highly Substituted Furan-Fused 1,4-Thiazepines and Their Diels-Alder Reactions with Benzynes

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• 作者：Hanfeng Ding ; Yiping Zhang ; Ming Bian ; Weijun Yao ; Cheng Ma
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 18, 2008
• 年：2008
• 卷：73
• 期：2
• 页码：578 - 584
• 全文大小：135K
• 年卷期：v.73,no.2(January 18, 2008)
• ISSN：1520-6904

文摘

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A facile and highly efficient three-component reaction of thiazole or benzothiazole carbenes, disubstitutedketenes, and activated alkynes is disclosed. With this methodology, a polysubstituted ring system containingfuro[2,3-c]thiazepine core can be constructed from simple and readily accessible starting materials ingood yields. The scope and limitation of this transformation were investigated in detail by using variousthiazole carbene, ketene, and alkyne components. Furthermore, the synthetic utilities of these uniquepolyheterocyclic compounds were demonstrated via their Diels-Alder reactions with benzynes to furnishthiazepine-fused 7-oxanorbornadiene derivatives in excellent yields.