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Cyclization of substituted 3,4-diaminopyridines into 1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxide derivatives during the nitration process

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Abstract

The nitration of pyridine-3,4-diamine, its N,N′-diacetyl derivative, and N 4-alkylpyridine-3,4-diamines with excess nitric acid in concentrated sulfuric acid at 60°C was accompanied by cyclization with formation of the corresponding 1-substituted 4-nitro-1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxides. 4-Chloro-1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxide derivatives were obtained under analogous conditions from 2-chloropyridine-3,4-diamine, its N,N′-diacetyl derivative, and 2-chloro-N 4-methylpyridine-3,4-diamine. The nitration of these compounds at 80–90°C gave 4-chloro-7-nitro-1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxides.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Lyuksemburg 70, Donetsk, 83114, Ukraine

    N. N. Smolyar & A. B. Vasilechko

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  1. N. N. Smolyar
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  2. A. B. Vasilechko
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Correspondence to N. N. Smolyar.

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Original Russian Text © N.N. Smolyar, A.B. Vasilechko, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 8, pp. 1217–1220.

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Smolyar, N.N., Vasilechko, A.B. Cyclization of substituted 3,4-diaminopyridines into 1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxide derivatives during the nitration process. Russ J Org Chem 46, 1219–1222 (2010). https://doi.org/10.1134/S1070428010080178

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  • DOI: https://doi.org/10.1134/S1070428010080178

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