The structure of the condensation products of
2-hydroxybenzohydrazide, 2-aminobenzohydrazide, and N-methyl-N-(2-aminobenzo) hydrazide with a series of aldoses
(L-arabinose, D-ribose, L- rhamnose, D-galactose, D-glucose, and D-mannose) was
studied by 1H- and 13C-NMR spectroscopy. The condensation
products of aldoses with 2-hydroxybenzohydrazide and 2-aminobenzohydra- zide in
DMSOd6 solutions exist as
equilibrium mixtures of linear acylhydrazone and cyclic pyranose and furanose
forms. The aldoses condensation products with N-methyl-N-(2-aminobenzo)hy- drazide in the crystalline state and in DMSOd6 solutions have cyclic benzo-1,2,4-triazepin
structure.
Cite this paper
Lagoda, I. V. , Ershov, A. Y. , Yakimovich, S. I. , Vasileva, M. Y. , Polukeev, V. A. , Kuleshova, L. Y. , Korovina, I. S. and Shamanin, V. V. (2016). Structure of Aldoses Condensation Products with 2-Hydroxy- and 2-Aminobenzohydrazides. Open Access Library Journal, 3, e2636. doi: http://dx.doi.org/10.4236/oalib.1102636.
El-Barbary, A.A., El-Ezz, A.Z.A., Sharaf, A.M. and Nielsen, C. (2006)
The Synthesis of Some New Quinazolone Derivatives of Potential Biological
Activity. Phosphorus, Sulfur, Silicon, 181, 1895-1912. http://dx.doi.org/10.1080/10426500500543834
Majumdar, P., Pati, A., Patra, M., Behera,
R.K. and Behera, A.K. (2012) Acid Hydrazides, Potent Reagents for Synthesis of Oxygen,
Nitrogen, and/or Sulfur-Containing Heterocyclic Rings. Chemical Reviews, 114, 2942-2977. http://dx.doi.org/10.1021/cr300122t
Gál, M., Tihanyi, E. and Dvortsák, P. (1986)
Ring-Chain Tautomerism of Ortho-Aminosubstituted Aromatic Carbo-xylic Acid
Hydrazones. I. Formation of 1,2,3,4-Tetrahydro-5H-1,3,4-Benzotriazepin-4-Ones. Acta
Chimica Hungarica, 123, 55-61.
Pihlaja, K., Simeonov, M.F. and Fülop, F. (1997)
Conformational Complexity in Seven-Membered Cyclic Triazepi-none/Open
Hydrazones. Part 1: 1-D
and 2-D Variable Temperature NMR Study. Journal
of Organic Chemistry, 62, 5080-5088. http://dx.doi.org/10.1021/jo962322k
Flegontov, S.A., Titova, Z.S., Stolyarov, A.P., Buzykin, B.I., Kitaev, Y.P. (1979) Hydrazones 62. The Structures
of Aroylhydrazones with Intramolecular Hydrogen Bonding. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 28,
948-953. http://dx.doi.org/10.1007/BF00963303