Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide – a new cyclic ketomethylenic reagent for the Dimroth-type 1,2,3-triazole synthesis

Abstract

A series of 1,5,6,7-tetrahydrothiopyrano[2,3-d][1,2,3]triazole 4,4-dioxides, new triazole-based bicyclic ring system, were prepared via base-mediated click reaction of organic azides with the readily available dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide. The reaction proceeded at room temperature in 5-12 h with catalysis by base-solvent system K₂CO₃/DMSO. High purity products were isolated by simple filtration and no formation of side products was observed. The key structure was confirmed by an X-ray study.

Graphical Abstract

Keywords:

• Azide
• click reaction
• thiopyranone
• 1,2,3-triazoles
• sulfone

Acknowledgment

The authors thank Dr Evgeny Goreshnik (Department of Inorganic Chemistry and Technology, Jozef Stefan Institute) and Dr Yuriy Slyvka (Department of Inorganic Chemistry, Ivan Franko National University of Lviv) for X-ray crystallographic analysis.

Additional information

Funding

The authors thank the Ministry of Education and Science of Ukraine for financial support of this project [grants 0118U003610 and 0119U100724].