Ding Hanfeng, Zhang Yiping, Bian Ming, Yao Weijun, Ma Cheng
Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
J Org Chem. 2008 Jan 18;73(2):578-84. doi: 10.1021/jo702299m. Epub 2007 Dec 13.
A facile and highly efficient three-component reaction of thiazole or benzothiazole carbenes, disubstituted ketenes, and activated alkynes is disclosed. With this methodology, a polysubstituted ring system containing furo[2,3-c]thiazepine core can be constructed from simple and readily accessible starting materials in good yields. The scope and limitation of this transformation were investigated in detail by using various thiazole carbene, ketene, and alkyne components. Furthermore, the synthetic utilities of these unique polyheterocyclic compounds were demonstrated via their Diels-Alder reactions with benzynes to furnish thiazepine-fused 7-oxanorbornadiene derivatives in excellent yields.
公开了一种噻唑或苯并噻唑卡宾、二取代烯酮和活化炔烃的简便且高效的三组分反应。通过这种方法，可以从简单且易于获得的起始原料以良好的产率构建含呋喃并[2,3-c]噻氮平核心的多取代环系统。通过使用各种噻唑卡宾、烯酮和炔烃组分详细研究了这种转化的范围和局限性。此外，通过这些独特的多杂环化合物与苯炔的狄尔斯-阿尔德反应，以优异的产率提供噻氮平稠合的7-氧杂降冰片二烯衍生物，证明了它们的合成效用。
