Abstract
The reaction of nitromalonaldehyde with 2-aminothiophenes leads to 5-nitrothieno-[2,3-b]pyridines. The analogous reaction with 3-aminopyrroles leads to 6-nitropyrrolo [3,2-b]pyridines. The analogous reaction with 4- and 5-aminopyrazoles leads to 6-nitropyrazolo[4,3-b]pyridines and 5-nitropyrazolo[3,4-b]pyridines, respectively. Enamines are formed as intermediates. 3- and 5-Aminopyrazoles which are unsubstituted at N-1 are converted to 3-nitropyrazolo[1,5-a]pyrimidines. The nitro derivatives obtained may be reduced to the corresponding amines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1471–1475, November, 1983.
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Schäfer, H., Gewald, K. & Schmidt, M. 5,6-Condensed 3-nitropyridines from heterocyclic amines and nitromalonaldehyde. Chem Heterocycl Compd 19, 1163–1166 (1983). https://doi.org/10.1007/BF00515347
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DOI: https://doi.org/10.1007/BF00515347