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An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates

Kotaro Ishihara, Takayuki Shioiri, Masato Matsugi

2020Organic Letters30 citationsDOI

Abstract

A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide–oxygen for elimination and azide source. Various amides were converted into the corresponding tetrazoles in good yields. This synthetic method allows to prepare 1,5-disubstituted and 5-substituted 1H-tetrazoles from various amides without the use of toxic or explosive reagents.

Topics & Concepts

ChemistryCombinatorial chemistrySynthesis of Tetrazole DerivativesQuinazolinone synthesis and applications