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Cascade Synthesis of 5-Aminotetrazoles from Isonitriles and N,N-Dibromoarylsulfonamides via Carbodiimide Coupling with Azide

Debashish Mishra, Sauvik Kashyap and Prodeep Phukan*

*Department of Chemistry, Gauhati University, Guwahati, Assam 781014, India, Email: pphukangauhati.ac.in

D. Mishra, S. Kashyap, P. Phukan, J. Org. Chem., 2023, 88, 9401-9408.

DOI: 10.1021/acs.joc.3c00041


Abstract

A cascade reaction of isonitriles with N,N-dibromoarylsulfonamides and sodium azide provide aminotetrazoles in the presence of K2CO3 at room temperature. This metal-free process proceeds via an isolable carbodiimide intermediate, which could further react with sodium azide and subsequently cyclizes intermolecularly to provide 5-aminotetrazoles within a short reaction time.

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proposed mechanism



Key Words

tetrazoles, multicomponent reactions


ID: J42-Y2023