Design,synthesis,and antimicrobial activity of fused triheterocyclic nitrogen systems involving tetrazolo[1,5-b][1,2,4]triazines[1]

摘要

Dehydrogenative cyclization of the 6-substi-tuted 7-arylidenehydrazinotetrazolo[1,5-b][1,2,4]tri-azines derived from 6-methyl and 6-phenyl derivatives of 7-hydrazinotetrazolo[1,5-b][1,2,4]triazines and aromatic aldehydes gave the corresponding 6-substi-tuted 9-aryl-[1,2,4]triazolo[4,3-d]tetrazolo-[1,5-b]-[1,2,4]triazines.The latter compounds were also obtained by an alternative route involving dehydrative cyclization of 6-methyl and 6-phenyl derivatives of 7-chlorotetrazolo[1,5-b][1,2,4]triazines with aromatic hydrazides through the isolable aroylhydrazino intermediates.Also,the triazolotetrazolotriazine rings were accomplished by one-pot cyclization of cyclic amidrazones with aromatic acid chlorides.The di-tetrazolo[1,5-b:l',5'-d][1,2,4]triazine systems were synthesized by cyclization of the former cyclic amidrazones with nitrous acid,or cyclic imidoyl chlorides with sodium azide.The bis-triazolotetrazolotriazine derivatives were synthesized by cyclization of two equivalents of each cyclic imidoyl chloride with acid dihydrazides through the isolable bis-hydrazide products.The antimicrobial activity of representative compounds was studied.