2-Alkyl-4-amino-5-(tert-butyl-NNO-azoxy)-2H-1,2,3-triazole 1-oxides: synthesis and reduction

• Published in: Russian chemical bulletin Vol. 63; no. 1; pp. 123 - 129
• Main Authors: Zelenov, V. P., Voronin, A. A., Churakov, A. M., Strelenko, Yu. A., Tartakovsky, V. A.
• Format: Journal Article
• Language: English
• Published: Boston Springer US 2014
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Full Articles; Inorganic Chemistry; Organic Chemistry; 1,2,3-triazole 1-oxides; C; N NMR spectroscopy; aminofuroxans; methylation; H; alkylation; 1,2,3-triazoles; butylazoxy group
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-014-0405-1

A new approach to the synthesis of 4-amino-5-( tert -butyl- NNO -azoxy)-2-R-2 H -1,2,3-triazole 1-oxides 1 was developed. Compounds 1 were obtained by reactions of 3-amino-4-( tert -butyl- NNO -azoxy)furoxan with aliphatic amines RNH 2 (R = Me, Et, Pr i , Bu, and Bu t ). 4-Amino-5-( tert -butyl- NNO -azoxy)-2- tert -butyl-2 H -1,2,3-triazole 1-oxide was transformed under the action of acids into 4-amino-5-( tert -butyl- NNO -azoxy)-1-hydroxy-1 H -1,2,3-triazole. Methylation of the latter with diazomethane mainly involves the O atom of the triazole oxide ring. Reduction of compounds 1 gave 4-amino-5-( tert -butyl- NNO -azoxy)-2-R-2 H -1,2,3-triazoles and 4-amino-5-( tert -butyldiazenyl)-2-R-2 H -1,2,3-triazoles (R = Me, Pr i , and Bu t ). The structures of the compounds obtained were confirmed by 1 H, 13 C, and 14 N NMR spectroscopy.