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Note | Regular issue | Vol 65, No. 10, 2005, pp.2471-2481
Published online, 23rd August, 2005
DOI: 10.3987/COM-05-10481
1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5’-(Z)-Diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) Derived from Chloronitrobenzotriazoles and Hydrazine

Antonio Carta,* Sandra Piras, Gianpiero Boatto, and Giuseppe Paglietti

*Department of Medicinal and Toxicological Chemistry, University of Sassari, Via Muroni 23, 07100 Sassari, Italy


Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4-nitrobenzotriazole (6) and 6-chloro-1-methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4-nitrobenzotriazole (8) or 5-chloro-2-methyl-4,6-dinitrobenzotriazole (9). Introduction of the nitro group activated chlorine atom that underwent nucleophilic displacement by hydrazine to give rise to a new tricyclic system 1H,6H-triazolo[4,5-e]benzotriazole-3-oxide compounds (10 and 11) in the case of 5 and 6. From 9 no linear or angular tricyclic triazolobenzotriazole was obtained but instead the 5,5’-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).