Survey reactivity of 5-substituted tetrazoles toward pentafluoropyridine

Abstract

Reactivity of some 5-substituted tetrazoles with pentafluoropyridine under basic conditions in acetonitrile was investigated. The reaction of pentafluoropyridine with tetrazoles regioselectively occurs at the 4-position of pyridine ring by N2 in the tetrazole ring. Tetrazoles with substituents at the position 5 such as Ph, 4-NO2C6H4, 4-CF3CONHC6H4, 4-ClC6H4CH2, EtOOCCH2, and 5-tetrazolyl−CH2 gave products containing unchanged tetrazole moiety. In contrast, tetrazole with substituents at the position 5 such as 3-(5-tetrazolyl)C6H4, 4-MeOC6H4, and 3-CF3CONHC6H4, gave hydrazide products via degradation of tetrazole ring.