Abstract
A new approach to the synthesis of 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-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 RNH2 (R = Me, Et, Pri, Bu, and But). 4-Amino-5-(tert-butyl-NNO-azoxy)-2-tert-butyl-2H-1,2,3-triazole 1-oxide was transformed under the action of acids into 4-amino-5-(tert-butyl-NNO-azoxy)-1-hydroxy-1H-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-2H-1,2,3-triazoles and 4-amino-5-(tert-butyldiazenyl)-2-R-2H-1,2,3-triazoles (R = Me, Pri, and But). The structures of the compounds obtained were confirmed by 1H, 13C, and 14N NMR spectroscopy.
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Dedicated to Academician of the Russian Academy of Sciences A. I. Konovalov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0123–0129, January, 2014.
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Zelenov, V.P., Voronin, A.A., Churakov, A.M. et al. 2-Alkyl-4-amino-5-(tert-butyl-NNO-azoxy)-2H-1,2,3-triazole 1-oxides: synthesis and reduction. Russ Chem Bull 63, 123–129 (2014). https://doi.org/10.1007/s11172-014-0405-1
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DOI: https://doi.org/10.1007/s11172-014-0405-1