Practical synthesis of tetrazoles from amides and phosphorazidates in the presence of aromatic bases

Abstract

Tetrazoles were effectively synthesized from amides using diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate in the presence of aromatic bases. Various amides underwent the proposed cycloaddition reaction to provide the corresponding tetrazoles. Studies on the racemization of chiral substrates were also performed. Overall, the proposed synthesis method enables the preparation of 1,5-disubstituted and 1-substituted tetrazoles, and 5-substituted 1H-tetrazoles without using toxic or explosive reagents.