Russian Journal of Organic Chemistry

, Volume 46, Issue 9, pp 1305–1312 | Cite as

Synthesis and reactions with N-nucleophiles of 1-(thien-2-yl)- and 1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones

Article

Abstract

Acylation of thiophene and phenol with 3,4,4-trichloro-3-butenoyl chloride afforded the corresponding 1-(thien-2-yl)- and 1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones, whose reaction with amines led to the formation of 3-amino-1-(thien-2-yl, 4-hydroxyphenyl)-4,4-dichloro-2-buten-1-ones The heterocyclization of the initial ketones into pyrazole structure was not observed, and the reaction with hydrazine hydrate provided bispyrazole products, N,N′-bis(5-thien-2-yl)- and N,N′-bis[5-(4-hydroxyphenyl)-1H-pyrazol-3-ylmethylene]hydrazines.

Keywords

Thiophene Hydrazine Hydrate Semicarbazide Semicarbazones Monoethanolamine 

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References

  1. 1.
    Pohland, A.E. and Benson, W.R., Chem. Rev., 1966, vol. 66, p. 161.CrossRefGoogle Scholar
  2. 2.
    Kaberdin, R.V., Potkin, V.I., and Petkevich, S.K., Vestsi Akad Nauk, Ser. Khim., 2006, 2, 99.Google Scholar
  3. 3.
    Potkin, V.I., Kaberdin, R.V., Petkevich, S.K., and Kurman, P.V., Zh. Org. Khim., 2002, 38, 1150.Google Scholar
  4. 4.
    Potkin, V.I., Petkevich, S.K., and Kurman, P.V., Zh. Org. Khim., 2007, 43, 1626.Google Scholar
  5. 5.
    Petkevich, S.K., Potkin, V.I., and Kaberdin, R.V., Zh. Org. Khim., 2006, 42, 1496.Google Scholar
  6. 6.
    Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Pesticides: Chemistry, Technology, and Application), Moscow: Khimiya, 1987.Google Scholar
  7. 7.
    Hafez, H.N. and El-Gazzar, A.B.A., Bioorg. Med. Chem. Lett., 2008, 18, 5222.CrossRefGoogle Scholar
  8. 8.
    Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2001, vol. 2, p. 386.Google Scholar
  9. 9.
    Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Fundamentals of Organic Chemistry of Medicines), Moscow: Mir, 2003, p. 62.Google Scholar
  10. 10.
    Petkevich, S.K., Dikusar, E.A., Potkin, V.I., Kaberdin, R.V., Moiseichuk, K.L., Yuvchenko, A.P., and Kurman, P.V., Zh. Org. Khim., 2004, vol. 74, p. 642.Google Scholar
  11. 11.
    Takhistov, V.V., Prakticheskaya mass-spektrometriya organicheskikh soedinenii (Practical Spectrometry of Organic Compounds), Leningrad: Izd. Leningrad. Gos. Univ., 1977, p. 265.Google Scholar
  12. 12.
    Takhistov, V.V., Rodin, A.A., and Maksimova, B.N., Usp. Khim., 1991, vol. 60, p. 2143.Google Scholar
  13. 13.
    Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Personal Reactions in Organic Chemistry), Moscow: Khimiya, 1976, p. 431.Google Scholar
  14. 14.
    Roedig, A. and Ritschel, W., Lieb. Ann., 1983, vol. 1, p. 13.Google Scholar
  15. 15.
    Roedig, A. and Ritschel, W., Chem. Ber., 1983, vol. 116, p. 1595.CrossRefGoogle Scholar
  16. 16.
    Bellamy, L.J., The Infra-red Spectra of Complex Molecules, London: Methuen, 1958.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • V. I. Potkin
    • 1
  • S. K. Petkevich
    • 1
  • P. V. Kurman
    • 1
  1. 1.Institute of Physical Organic ChemistryNational Academy of Sciences of BelarusMinskBelarus

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