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Structure of Aldoses Condensation Products with 2-Hydroxy- and 2-Aminobenzohydrazides

DOI: 10.4236/oalib.1102636, PP. 1-6

Subject Areas: Organic Chemistry

Keywords: Aldoses 2-Hydroxy- and 2-Aminobenzohydrazides, Benzo-1,2,4-Triazepines, Ring-Chain-Ring Tautomerism

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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.

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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:


[1]  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.
[2]  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.
[3]  Kahl, R. (1904) über die Paarung von Saurehydraziden mit Zuckerarten. Chemisches Zentralblatt, 75, 1493-1494.
[4]  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.
[5]  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.
[6]  Alekseev, V.V., Ershov, A.Y., Chernitsa, B.V., Doroshenko, V.A., Lagoda, I.V., Yakimovich, S.I., Zerova, I.V., Pakalnis, V.V. and Shamanin, V.V. (2010) Structure of Aldoses Condensation Products with 2-Hydroxy- and 2-Sulfanyl-Benzohydrazides. Russian Journal of Organic Chemistry, 46, 860-865.
[7]  Ershov, A.Y., Chernitsa, B.V., Doroshenko, V.A.,·Yakimovich, S.I., Alekseyev, V.V., Lagoda, I.V., Pakalnis, V.V., Zerova, I.V. and Shamanin, V.V. (2011) N-(2-Aminobenzoyl)-N-Methylhydrazones of Aldehydes and Aldoses and Their Cyclization to Benzo-1,3,4-Triazepine Derivatives. Chemistry of Heterocyclic Compounds, 46, 1486-1493.
[8]  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.


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