Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles

详细信息    查看全文

• 作者：Suvajit Koley ; Tanmoy Chanda ; Subhasis Samai ; Maya Shankar Singh
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：81
• 期：23
• 页码：11594-11602
• 全文大小：628K
• ISSN：1520-6904

文摘

An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from α-enolic dithioesters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl₃ under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self-coupling of dithioesters in open air enabling the formation of two new C–S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of 1,2- and 1,3-dithioles from α-enolic dithioesters have been suggested.