Russian Journal of Organic Chemistry

, Volume 44, Issue 8, pp 1211–1214 | Cite as

Reaction of 4,5-dichloro-3-trichloromethylisothiazole with heterocyclic amines

  • V. I. Potkin
  • Yu. S. Zubenko
  • S. K. Petkevich


4,5-Dichloro-3-trichloromethylisothiazole reacted with piperidine, morpholine, pyrrolidine, and piperazine in DMF to give 81–96% of the corresponding 5-amino-4-chloro-3-trichloromethylisothiazoles as a result of selective nucleophilic replacement of the 5-chlorine atom. Acylation of 4-chloro-5-(piperazin-1-yl)-3-trichloromethylisothiazole with acetyl chloride gave 4-chloro-5-(4-acetylpiperazin-1-yl)-3-trichloromethyl-isothiazole.


Piperazine Acetyl Chloride Heterocyclic Amine Trichloromethyl Methylene Carbon Atom 
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  1. 1.
    Clerici, F., Gelmi, M-L., Pellegrino, S., and Pocar, D., Top. Heterocycl. Chem., 2007, vol. 9, p. 179.CrossRefGoogle Scholar
  2. 2.
    Burli, R.W., Ge, Y., White, S., Baird, E.E., Touami, S.M., Taylor, M., Kaizerman, J.A., and Moser, H.E., Bioorg. Med. Chem. Lett., 2002, vol. 12, p. 2591.CrossRefGoogle Scholar
  3. 3.
    Kaizerman, J.A., Gross, M.I., Ge, Y., White, S., Hu, W., Duan, J.-X., Baird, E.E., Johnson, K.W., Tanaka, R.D., Moser, H.E., and Burli, R.W., J. Med. Chem., 2003, vol. 46, p. 3914.CrossRefGoogle Scholar
  4. 4.
    Kaberdin, R.V., Potkin, V.I., and Ol’dekop, Yu.A., Dokl. Akad. Nauk SSSR, 1988, vol. 300, p. 1133.Google Scholar
  5. 5.
    Kaberdin, R.V. and Potkin, V.I., Usp. Khim., 2002, vol. 71, p. 764.Google Scholar
  6. 6.
    Kaberdin, R.V., Potkin, V.I., and Ol’dekop, Yu.A., Zh. Org. Khim., 1990, vol. 36, p. 1560.Google Scholar
  7. 7.
    Reichardt, C., Solvents and Solvent Effects in Organic Chemistry, Weinheim: VCH, 1988, 2nd ed.Google Scholar
  8. 8.
    Pain, D.L., Peart, B.J., and Wooldridge, K.R.H., Comprehensive Heterocyclic Chemistry, Katritzky, A.R. and Rees, C.W., Eds., Oxford: Pergamon, 1984, vol. 6, p. 131.Google Scholar
  9. 9.
    Takhistov, V.V., Prakticheskaya mass-spektrometriya organicheskikh soedinenii (Practical Mass Spectrometry of Organic Compounds), Leningrad: Leningr. Gos. Univ., 1977, p. 265.Google Scholar
  10. 10.
    Takhistov, V.V., Rodin, A.A., and Maksimova, B.N., Usp. Khim., 1991, vol. 60, p. 2143.Google Scholar
  11. 11.
    Poite, J.C., Vivaldi, R.V., and Bonzom, A., C.R. Acad. Sci., Ser. C, 1969, vol. 268, p. 12.Google Scholar
  12. 12.
    Naito, T., Tetrahedron, 1968, vol. 24, p. 6237.CrossRefGoogle Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

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

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