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

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. (C) 2022 Elsevier Ltd. All rights reserved.

Automated summary

Tetrazoles can be effectively synthesized using non-toxic or explosive reagents, diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate, in the presence of aromatic bases.