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通过多米诺骨牌式偶联/环化反应,由α-氧代烯酮二硫代缩醛和炔丙醇方便地进行碱介导合成3-芳基-4-甲基(或苄基)-2-甲硫基呋喃。

A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations.

作者信息

Yang Xiaobing, Hu Fangzhong, Di Hongjing, Cheng Xinxin, Li Dan, Kan Xiaoli, Zou Xiaomao, Zhang Qichun

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.

出版信息

Org Biomol Chem. 2014 Nov 28;12(44):8947-51. doi: 10.1039/c4ob01300j.

Abstract

A convenient base-mediated strategy to synthesize 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations between available α-oxo ketene dithioacetals 1 and propargyl alcohols. In this strategy, these types of bases play an important role in driving the domino coupling reaction of propargyl alcohols and further intramolecular annulations to realize the target compounds. The possible mechanism for the formation of the various products is believed to involve the generation of allenes 7, followed by intramolecular annulations.

摘要

通过可用的α-氧代烯酮二硫代缩醛1与炔丙醇之间的多米诺偶联/环化反应,开发了一种便捷的碱介导策略来合成3-芳基-4-甲基(或苄基)-2-甲硫基呋喃2(三取代呋喃)。在该策略中,这些类型的碱在驱动炔丙醇的多米诺偶联反应以及进一步的分子内环化反应以实现目标化合物方面起着重要作用。据信,形成各种产物的可能机制涉及丙二烯7的生成,随后是分子内环化反应。

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