The products of the condensation of aliphatic aldehydes with N-(2-aminobenzoyl)-N-methylhydrazine exist in DMSO-d6 solution as tautomeric mixtures of linear aldohydrazone and cyclic benzo-1,3,4-triazepine forms. The linear tautomer predominates for 2-aminobenzoyl-N-methylhydrazones of aromatic aldehydes. A tautomeric equilibrium is observed in DMSO-d6 for the products of the condensation of the hydrazide of 2-aminobenzoic acid with a series of aldoses. This equilibrium exists between α,β-isomeric pyranose forms and the open aldosohydrazone form. Isomeric conversion to the seven-membered benzo-1,3,4-triazepine form is observed for the products of the condensation of aldoses with N-(2-aminobenzoyl)-N-methylhydrazine.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1838–1848, December, 2010.
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Ershov, A.Y., Chernitsa, B.V., Doroshenko, V.A. et al. N-(2-aminobenzoyl)-N-methylhydrazones of aldehydes and aldoses and their cyclization to benzo-1,3,4-triazepine derivatives. Chem Heterocycl Comp 46, 1486–1493 (2011). https://doi.org/10.1007/s10593-011-0697-0
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DOI: https://doi.org/10.1007/s10593-011-0697-0