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Synthesis of 1,3,4-Thiadiazoles and 1,4,2-Oxathiazoles from α-Enolic Dithioesters and Active 1,3-Dipoles

Bin Cheng, Hui Li, Jianguo Sun, Xinping Zhang, Yixuan He, Haiyan Sun, Wei Xu, Taimin Wang, Hongbin Zhai

2021The Journal of Organic Chemistry18 citationsDOI

Abstract

The synthesis of two kinds of five-membered organosulfur heterocycles (i.e., 1,4,2-oxathiazoles and 1,3,4-thiadiazoles) from α-enolic dithioesters with active 1,3-dipoles (nitrile oxides and nitrilimines) generated in situ was achieved under mild reaction conditions. This transformation further expands the synthetic application of α-enolic dithioesters as the sulfur-containing building blocks.

Topics & Concepts

ChemistryThiadiazolesOrganosulfur compoundsNitrileDipoleSulfurOrganic chemistryCombinatorial chemistrySulfur-Based Synthesis TechniquesSynthesis of heterocyclic compoundsSynthesis and Catalytic Reactions