[3 + 3] Cycloaddition of aza-oxyallyl cations with 1, 4-dithiane-2, 5-diols for the construction of 3-thiomorpholinones. Issue 9 (2nd May 2020)

• Record Type: Journal Article
• Authors: Xie, Lei; Guo, Sheng-nan; Wu, Ping; Gao, Zhenzhen; Liu, Fang; Yuan, Chunhao
• Is Part Of: Synthetic communications. Volume 50:Issue 9(2020)
• Page Start: 1375
• Page End: 1387
• Publication Date: 2020-05-02
• Subjects: Azaoxyallyl cations -- cycloaddition -- 1, 4-dithiane-2, 5-diols -- novel bonding mode -- thiomorpholin-3-ones; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2020.1740738
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Base-mediated [3 + 3] cycloaddition reaction of in-situ formed aza-oxyallyl cations and 1, 4-dithiane-2, 5-diols has been achieved under mild reaction conditions. This strategy provides direct and efficient access to prepare desired thiomorpholin-3-one derivatives in moderate-to-high yields. The approach features broad substrates scope and short reaction time. Moreover, the resulting products can be readily converted into other useful heterocyclic compounds including 2 H -1, 4-thiazin-3(4 H )-ones and thiomorpholine-3, 5-diones. Graphical Abstract: