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Russian Chemical Bulletin

, Volume 53, Issue 9, pp 2060–2070 | Cite as

Heterocyclization of 2-chloro-1-cyano-1-diethoxyphosphoryl-2-trifluoromethylethylene and 2-chloro-2-chlorodifluoromethyl-1-cyano-1-diethoxyphosphorylethylene

  • A. F. Shidlovskii
  • A. S. Peregudov
  • B. B. Averkiev
  • M. Yu. Antipin
  • N. D. Chkanikov
Article

Abstract

The reactions of 2-chloro-1-cyano-1-diethoxyphosphoryl-2-trifluoromethylethylene (2a) and 2-chloro-2-chlorodifluoromethyl-1-cyano-1-diethoxyphosphorylethylene (2b) with arylamines, arylhydrazines, amidines, 2-aminopyridines, and 5-aminopyrazoles were studied. Alkenes 2a, b can serve as precursors of aminopyrazoles, pyrimidines, pyrido[1,2-a]pyrimidines, and pyrazolo[1,5-a]pyrimidines modified with the fluoroalkyl and diethoxyphosphoryl groups. Intermediates of some heterocyclization reactions were detected by NMR spectroscopy. The structures of the compounds were confirmed by X ray diffraction analysis.

Key words

2-chloro-1,1-dicyano-2-trifluoromethylethylene 2-chloro-1-cyano-1-diethoxyphosphoryl-2- trifluoromethylethylene 2-chloro-2-chlorodifluoromethyl-1-cyano-1-diethoxyphosphorylethylene aminopyrazoles pyrimidines pyrido[1,2-a]pyrimidines pyrazolo[1,5-a]pyrimidines heterocyclization X-ray diffraction analysis 

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References

  1. 1. (a)
    V. I. Krokhtyak, A. Ya. Il’chenko, and L. M. Yagupol’skii, Zh. Org. Khim., 1980, 16, 1694 [J. Org. Chem. USSR, 1980, 16, 1441 (Engl. Transl.)]; (b) V. I. Krokhtyak, A. Ya. Il’chenko, and L. M. Yagupol’skii, Zh. Org. Khim., 1981, 17, 268 [J. Org. Chem. USSR, 1981, 17, 219 (Engl. Transl.)]; (c) A. Ya. Il’chenko, V. I. Krokhtyak, and L. M. Yagupol’skii, Khim. Geterotsikl. Soedin., 1981, 1680 [Chem. Heterocycl. Compd., 1981, 17, 1236 (Engl. Transl.)]; (d) A. Ya. Il’chenko, R. E. Koval’chuk, V. I. Krokhtyak, and L. M. Yagupol’skii, Zh. Org. Khim., 1981, 17, 2630 [J. Org. Chem. USSR, 1981, 17, 2348 (Engl. Transl.)]; (e) A. F. Shidlovskii, A. Yu. Sizov, L. N. Kuleshova, V. V. Nesterov, M. Yu. Antipin, A. S. Peregudov, and N. D. Chkanikov, Izv. Akad. Nauk, Ser. Khim., 2000, 1261 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1257].Google Scholar
  2. 2. (a)
    R. Filler, J. Fluorine Chem., 1986, 33, 361; (b) K. Tanura, H. Mizukami, K. Maeda, H. Watanabe, and K. Uneyama, J. Org. Chem., 1993, 58, 32 (and references cited therein).Google Scholar
  3. 3. (a)
    R. Engel, Chem. Rev., 1977, 349; (b) F. Palasios, A. Ochoa de Renata, and J. Oyarzabal, Tetrahedron, 1999, 5947; (c) M. R. Harnden, A. Parkin, M. J. Parrat, and R. M. Perkins, J. Med. Chem., 1993, 36, 1345; (d) A. A. Thomas and K. B. Sharpless, J. Org. Chem., 1999, 64, 8379; (e) Eur. Pat. 528, 760; Chem. Abstr., 1993, 119, 72837b; (f) Ger. Pat. 3, 736, 113; Chem. Abstr., 1990, 112, 112068.Google Scholar
  4. 4.
    Ya. G. Bal’on, B. N. Kozhushko, Yu. A. Paliichuk, and V. A. Shokol, Zh. Obshch. Khim., 1992, 62, 2530 [Russ. J. Gen. Chem. USSR, 1992, 62, 2089 (Engl. Transl.)].Google Scholar
  5. 5.
    A. J. Bondi, J. Phys. Chem., 1964, 68, 441.Google Scholar
  6. 6.
    V. Yu. Tyutin, N. D. Chkanikov, V. N. Nesterov, M. Yu. Antipin, Yu. T. Struchkov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk, Ser. Khim., 1993, 552 [Russ. Chem. Bull., 1993, 42, 512 (Engl. Transl.)].Google Scholar
  7. 7.
    J. S. Bajwa and P. J. Sykes, J. Chem. Soc., Perkin Trans. 1, 1979, 3085.Google Scholar
  8. 8.
    F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J Chem. Soc., Perkin Trans. 2, 1987, S1.Google Scholar
  9. 9.
    F. H. Allen, Acta Crystallogr., 2002, 58, 380.Google Scholar
  10. 10.
    G. M. Sheldrick, SHELXTL-97, Version 5.10, Bruker AXS Inc., Madison (WI-53719, USA), 1997.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2004

Authors and Affiliations

  • A. F. Shidlovskii
    • 1
  • A. S. Peregudov
    • 1
  • B. B. Averkiev
    • 1
  • M. Yu. Antipin
    • 1
  • N. D. Chkanikov
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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