Synthesis of some 4‐substituted‐2‐(o‐halogenophenyl)‐1,2,3‐triazoles

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Mesoaldehyde 1,3‐dioxime was treated with either 2,4,6‐trichlorophenyl‐ (a), o‐fluorophenyl‐ (b), or o‐bromophenyl‐ (c) hydrazine to give the corresponding mesoaldehyde 1,3‐dioxime‐2‐halogenophenylhydrazones (1a,b,c). The latter were O‐acetylated with acetic anhydride, and cyclized to triazole 4‐oximes (3b, c) or triazole 4‐O‐acetyloximes (6a,b,c) with cesium carbonate, then converted to nitriles (7a,b,c) by refluxing with acetic anhydride followed by pyrolysis, or to aldehydes (4a,b,c) by hydrolysis. The nitriles (7a,b,c) were also converted to acids (9a,b,c), esters (10a,b,c), amides (8a,c), an alcohol (11a), and an amine (12a). In addition, tetrazoles of two types were prepared. The first (13d,e) were obtained from the acid chlorides by the action of 5‐aminotetrazole, whereas the second (14f) was produced from the respective nitrile by the action of ammonium azide. Copyright © 1983 Journal of Heterocyclic Chemistry

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Journal of Heterocyclic Chemistry