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UDK: 547.781.1

2013. - V. 27. - N 4(144). - P. 22-26

Polina Andreevna Nikitina, Yevgenij Il’darovich Adiulin, Kirill Victorovich Rachkov, Tat’iana Yur’evna Koldaeva, Valerij Pavlovich Perevalov, Iosif Isaakovich Tkach,

SYNTHESIS AND STUDY OF PROPERTIES OF 2-(2-HYDROXYPHENYL)-1-HYDROXYIMIDAZOLE DERIVATIVES

In the course of study of prototropic tautomerism of 1-hydroxyimidazoles novel 2-(2-hydroxyphenyl)-substituted 1-hydroxyimidazoles have been synthesized. As model compounds for N-oxide tautomeric form of compounds under consideration novel 1-methylimidazoles 3-oxides have been obtained. A synthetic approach towards 1-methoxy-2-(2-hydroxyphenyl)-imidazoles has been worked out. These derivatives can be regarded as model structures for N-hydroxy tautomer.

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СИНТЕЗ И ИССЛЕДОВАНИЕ СВОЙСТВ ПРОИЗВОДНЫХ 2-(2-ГИДРОКСИФЕНИЛ)-1-ГИДРОКСИИМИДАЗОЛОВ

References

  1. Takahashi S., Kano H. Benzimidazole N-Oxides. I. The Structure of Benzimidazole N-Oxide and Synthesis of its Derivatives. // Chem. and Pharm. Bull. (Japan), 1963. _ 11. P. 1375-1381.
  2. Neadle D.J., Pollitt R.J. The photolysis of N-2,4-dinitrophenulamino-acids to give 2-substituted 6-nitrobenzimidazole 1-oxides. // J.Chem.Soc.(C), 1967. P. 1764-1766.
  3. Stacy G.W., Wollner T.E., Oakes T.R. Tautomeric Structure of 1-Oxy-2-phenylbenzimidazole. // J. Heterocycl. Chem., 1966. _3. R. 51-54.
  4. Volkamer K., Zimmermann H.W. Uber arylsubstituierte 1-Hydroxy-imidazole and 1-Hydroxy-imidazol-N3-oxide. // Chem. Ber., 1969. _102. P. 4177-4187.
  5. Chua S.O., Cook M.J., Katrizky A.R. The Tautomerism of Heteroaromatic Compounds with Five-membered Rings. Part XII. The Imidazole 3-Oxide versus 3-Hydroxy[3H]imidazole Equilibrium. // J. Chem. Soc. B, 1971. P. 2350-2355.
  6. Aquirre G., Boiani M., Cerecetto H., Gerpe A., Gonzalez M., Sainz Y.F., Denicola A., Ochoade Ocariz C., Nogal J.J., Montero D., Escario J.A. Novel Antiprotozoal Products: Imidazole and Benzimidazole N-Oxide Derivatives and Related Compounds. // Arch. Pharm. Pharm. Med. Chem., 2004. _337. R. 259-270.
  7. Boiani M., Cerecetto H., Gonzalez M., Piro O.E., Castellano E.E. Tautomerism and Reactivity in Heterocyclic N-Oxides. A Spectroscopic and Theoretical Study of Benzimidazole N-Oxide Derivatives (N-Hydroxybenzimidazoles). // J.Phys.Chem. A, 2004. _108. R. 11241-11248.
  8. Nikitina P.A., Kuz_mina L.G., Perevalov V.P., Tkach I.I. Synthesis and Study of Prototropic Tautomerism of 2-(3-Chromenyl)-1-hydroxyimidazoles. // Tetrahedron, 2013. _69. P. 3249-3256.
  9. Wolff L. Ueber Diazoanhydride. // Justus LiebigsAnnalen der Chemie, 1902. _325 (2). S. 129-195.

Keywords

1-hydroxyimidazole   1-methoxyimidazole   1-гидроксиимидазол   imidazole-N-oxide   N-оксид имидазола, 1-метоксиимидазол, прототропная таутомерия imidazole   prototropic tautomerism   имидазол  


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