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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Authors: | N N Smolyar A B Vasilechko |
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Institution: | 1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Lyuksemburg 70, Donetsk, 83114, Ukraine
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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]triazolo4,5-c]pyridine 2-oxides. 4-Chloro-1H-1,2,3]triazolo4,5-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]triazolo4,5-c]pyridine 2-oxides. |
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