Abstract
Dehydrogenative cyclization of the 6-substituted 7-arylidenehydrazinotetrazolo[1,5-b][1,2,4]triazines 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-substituted 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 ditetrazolo[1,5-b:1′,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.
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Correspondence: Mamdouh A. M. Taha, Chemistry Department, Faculty of Science, Faiyoum University, Faiyoum 63514, Egypt.
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Taha, M., El-Badry, S. Design, synthesis, and antimicrobial activity of fused triheterocyclic nitrogen systems involving tetrazolo[1,5-b][1,2,4]triazines [1]. Monatsh Chem 139, 1261–1267 (2008). https://doi.org/10.1007/s00706-008-0902-8
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DOI: https://doi.org/10.1007/s00706-008-0902-8