Carta, Antonio and Piras, Sandra and Boatto, Gianpiero and Paglietti, Giuseppe (2005) 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. Heterocycles, Vol. 65 (10), p. 2471-2481. ISSN 0385-5414. Article.
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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).
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