Recent Advances in the Denitrogenative Annulation Reactions of 1,2,3-Thiadiazoles

Publication Name

ChemCatChem

Abstract

1,2,3-Thiadiazoles exhibit versatile reactivity due to their ability to undergo ring cleavage, forming α-diazothione species through a Dimroth-type equilibrium. Denitrogenation of the α-diazothione, induced by high temperature, irradiation, or strong bases, allows generation of a wide range of reactive intermediates. Since 2016, the transition-metal-catalyzed denitrogenative transannulation of 1,2,3-thiadiazoles has garnered significant attention as a promising approach to constructing diverse heterocyclic scaffolds. This review focuses on the denitrogenative reactions of 1,2,3-thiadiazoles, particularly highlighting the novel rhodium-catalyzed denitrogenative transannulation transformations along with their mechanisms.

Open Access Status

This publication is not available as open access

Funding Sponsor

Macquarie University

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Link to publisher version (DOI)

http://dx.doi.org/10.1002/cctc.202301488