N-(2 AMINOBENZOYL)-N-METHYLHYDRAZONES OF ALDEHYDES AND ALDOSES AND THEIR CYCLIZATION TO BENZO-1,3,4-TRIAZEPINE DERIVATIVES
DOI:
https://doi.org/10.1007/6206Keywords:
2-aminobenzoylhydrazones, benzo-1, 3, 4-triazepines, ring-chain tautomerismAbstract
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 a,b-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.
How to Cite
Ershov, A. Yu.; Chernitsa, B. V.; Doroshenko, V. A.; Yakimovich, S. I.; Alekseyev, V. V.; Lagoda, I. V.; Pakal'nis, V. V.; Zerova, I. V.; Shamanin, V. V. Chem. Heterocycl. Compd. 2011, 46, 1486. [Khim. Geterotsikl. Soedin. 2010, 1838.]
