Russian Journal of Organic Chemistry

, Volume 41, Issue 5, pp 694–702 | Cite as

Reactions of Isomeric Arylchloropyruvates and Glycidates with Hydrazines

  • V. A. Mamedov
  • L. V. Mustakimova
  • A. T. Gubaidullin
  • I. A. Litvinov
  • Ya. A. Levin


Reactions of arylchloropyruvic acids esters with aryl- and hetarylhydrazines give rise to pyrazolinedione hydrazones as a result of a tandem condensation of the substituted hydrazines with arylchloropyruvates. In contrast to this process in reaction with hydrazine hydrate a ready reduction unexpectedly occurs by Kizhner-Wolff mechanism affording 3-hydroxydihydrocinnamic acid hydrazide as the principal product. The isomeric arylglycidate reacts along the same pattern.


Ester Hydrate Organic Chemistry Hydrazine Acid Ester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Kitaev, Yu.P and Buzykin, B.N., Gidrazony (Hydrazons), Kost, A.N., Ed., Moscow: Nauka, 1974, vol. 262, p. 370.Google Scholar
  2. 2.
    Ramirez, F. and Kirby, J., J. Am. Chem. Soc., 1953, vol. 23, p. 6026.Google Scholar
  3. 3.
    Pritzkow, W., Z. Chem., 1970, vol. 10, p. 330.Google Scholar
  4. 4.
    Hassner, A. and Catsonlaccos, P., Chem. Commun., 1967, p. 121.Google Scholar
  5. 5.
    Simon, H., Moldenhauer, W., and Kraus, A., Chem. Ber., 1969, vol. 102, p. 2777.Google Scholar
  6. 6.
    Stickler, W.C. and Hoffman, W.C., Angew. Chem., 1970, vol. 82, p. 254.Google Scholar
  7. 7.
    Roeding, A. and Wenzel, W., Lieb. Ann., 1969, vol. 728, p. 1.Google Scholar
  8. 8.
    Wharton, P.S., Dunug, S., and Krebs, L.S., J. Org. Chem., 1964, vol. 29, p. 958.Google Scholar
  9. 9.
    Crawford, R.J. and Tokunada, H., Canad. J. Chem., 1974, vol. 52, p. 4033.Google Scholar
  10. 10.
    Shvaika, O.P. and Artemov, V.N., Usp. Khim., 1972, vol. 10, p. 1788.Google Scholar
  11. 11.
    Slagel, R.S., J. Org. Chem., 1968, vol. 33, p. 1374.Google Scholar
  12. 12.
    Europe Patent 52333, 1996; Chem. Abstr., 1997, 144854g.Google Scholar
  13. 13.
    Shkineva, T.G., Dalinger, I.L., and Shevelev, S.A., Khim. Geterotsikl. Soed., 1995, p. 579.Google Scholar
  14. 14.
    Wolfrom, M.L. and Wood, H.B., J. Am. Chem. Soc., 1951, vol. 73, p. 2933.Google Scholar
  15. 15.
    Patai, S., The Chemistry of the Hygrazo, Azo, and Azoxy Groups, part I, 1975, p. 154.Google Scholar
  16. 16.
    Strakov, A.Ya., Petrova, M.V., Strakova, I.A., and Lakhovich, O.F., Khim. Geterotsikl. Soed., 1995, p. 336.Google Scholar
  17. 17.
    Mamedov, V.A., Valeeva, V.N., Antokhina, L.A., and Nuretdinov, I.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, p. 1422.Google Scholar
  18. 18.
    Mamedov, V.A., Berdnikov, E.A., Valeeva, V.N., Ismaev, I.E., Rizvanov, I.Kh., Antokhina, L.A., Nuretdinov, I.A., and Chernov, P.P., Izv. Akad. Nauk, Ser. Khim., 1993, p. 1962.Google Scholar
  19. 19.
    Mustakimova, L.V., Mamedov, V.A., and Levin, Ya.A., Khimiya i primenenie fosfor-, sera-, i kremniiorganicheskikh soedinenii (Chemistry and Application of Phosphor, Sulfur, and Silicon Containing Compounds), St. Petersburg, 1998, p. 107.Google Scholar
  20. 20.
    Singh, S.P., Kodai, D.R., Dhindsa, G.S., and Sawhney, S.N., Indian J. Chem., 1982, vol. 21B, p. 30.Google Scholar
  21. 21.
    Singh, S.P., Sehgal, S., Tarar, L.G., and Dhawan, S.N., Indian J. Chem., 1990, vol. 29B, p. 310.Google Scholar
  22. 22.
    Mahajan, M.P., Sondhi, S.M., and Ralhan, N.K., Austral. J. Chem., 1977, vol. 30, p. 2053.Google Scholar
  23. 23.
    Minkin, V.I., Olekhnovich, L.P., and Zhdanov, Yu.A., Molekulyarnyi dizain tautomernykh sistem (Molecular Design of Tautomeric Systems), Mikhailov, I.E., Rostov: Rostov. Gos. Univ., 1977, p. 271.Google Scholar
  24. 24.
    Alaka, B.V., Patnaik, D., and Rout, M.K., J. Indian Chem. Soc., 1982, vol. 69, p. 1168.Google Scholar
  25. 25.
    Gasteiger, J. and Herzig, Ch., Tetrahedron Lett., 1980, vol. 21, p. 2687.Google Scholar
  26. 26.
    Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Srystallogr. A, 1991, vol. 47, p. 744.Google Scholar
  27. 27.
    Straver, L.H. and Schierbeek, A.J., MolEN. Structure Determination System. 1. Program Description, Nonius, B.V., Ed., 1994.Google Scholar
  28. 28.
    Spek, A.L., PLATON. A Miltipurpouse Crystallographic Tool, Utrecht: Utrecht University Press, 2000, p. 214.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • V. A. Mamedov
    • 1
  • L. V. Mustakimova
    • 1
  • A. T. Gubaidullin
    • 1
  • I. A. Litvinov
    • 1
  • Ya. A. Levin
    • 1
  1. 1.Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific CenterRussian Academy of SciencesKazanRussia

Personalised recommendations