Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4nitrobenzotriazole (6) and 6-chloro-1 -methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4nitrobenzotriazole (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,6Htriazolo[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-l ,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).

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 / Carta, Antonio; Piras, Sandra; Boatto, Gianpiero; Paglietti, G.. - In: HETEROCYCLES. - ISSN 0385-5414. - 65:10(2005), pp. 2471-2481. [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

CARTA, Antonio;PIRAS, Sandra;BOATTO, Gianpiero;
2005

Abstract

Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4nitrobenzotriazole (6) and 6-chloro-1 -methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4nitrobenzotriazole (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,6Htriazolo[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-l ,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).
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 / Carta, Antonio; Piras, Sandra; Boatto, Gianpiero; Paglietti, G.. - In: HETEROCYCLES. - ISSN 0385-5414. - 65:10(2005), pp. 2471-2481. [10.3987/COM-05-10481]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/163708
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