[3 + 3] Cycloaddition of aza-oxyallyl cations with 1,4-dithiane-2,5-diols for the construction of 3-thiomorpholinones

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 2H-1,4-thiazin-3(4H)-ones and thiomorpholine-3,5-diones.

Graphical Abstract

Keywords:

• Azaoxyallyl cations
• cycloaddition
• 1,4-dithiane-2,5-diols
• novel bonding mode
• thiomorpholin-3-ones

Additional information

Funding

This work was supported by Natural Science Foundation of Shandong Province [ZR2018BB028, ZR2019BB054, ZR2018LB010].