Russian Chemical Bulletin

, Volume 43, Issue 1, pp 110–113 | Cite as

Synthesis of 3-thienyl substituted 2-pyrazolines by 1,3-dipolar cycloaddition

  • M. M. Krayushkin
  • M. A. Kalik
  • S. A. Voznesensky
Organic Chemistry


1,3,5-Trisubstituted 3-thienylpyrazolines have been prepared in high yields by the reaction of substituted,N-(P;-nitrophenyl)-3-thiophenecarbohydrazonoyl chlorides with Et3N in CH2Cl2 in the presence of an excess of a monosubstituted olefin. The reaction probably occurs as 1,3-dipolar cycloaddition of the corresponding 3-thiophenecarbonitrile imines formedin situ at the double bond of the olefin.

Key words

1,3-dipolar cycloaddition hydrazonoyl chlorides 3-thienylpyrazolines 3-thienylpyrazoles 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    M. M. Krayushkin, M. A. Kalik, V. K. Zav'yalova, and V. S. Bogdanov,Khim. Geterotsikl. Soed., 1988, 403 [Chem. Heterocycl. Comp., 1988 (Engl. Transl.)].Google Scholar
  2. 2.
    M. M. Krayushkin, M. A. Kalik, and A. Ya. Kudryavtseva,Izv. Akad. Nauk, Ser. Khim., 1992, 1892 [Bull. Acad. Sci., Div. Chem. Sci., 1992,41, 1477 (Engl. Transl.)].Google Scholar
  3. 3.
    M. M. Krayushkin, M. A. Kalik, V. K. Zav'yalova, A. A. Loktionov, and V. S. Bogdanov,Khim. Geterotsikl. Soed., 1989, 1620 [Chem. Heterocycl. Comp., 1989 (Engl. Transl.)].Google Scholar
  4. 4.
    F. Castan, A. Bacciredo, and G. Bertrand,Angew. Chem. Int. Ed., 1989,28, 1250.Google Scholar
  5. 5.
    G. Sicard, A. Bacciredo, and G. Bertrand,J. Am. Chem. Soc., 1988,110, 2663.Google Scholar
  6. 6.
    J. K. Stille, F. W. Harris, and M. A. Bedford,J. Heterocyclic Chem., 1966,3, 155.Google Scholar
  7. 7.
    G. E. Nilson,Tetrahedron, 1982,38, 2597.Google Scholar
  8. 8.
    S. V. Tsukerman, V. M. Nikitchenko, and V. F. Lavnishin,Khim. Geterotsikl. Soed., 1968, 1093; 1965, 693 [Chem. Heterocycl. Comp., 1968; 1965 (Engl. Transl.)].Google Scholar
  9. 9.
    W. Ried, G. Dankert,Chem. Ber., 1957,90, 2707.Google Scholar
  10. 10.
    T. Sasaki, T. Joshioka,Bull. Chem. Soc. Jpn., 1970,43, 1254.Google Scholar
  11. 11.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova,Zh. Org. Khim., 1960,30, 1012 [J. Ogr. Chem., 1960,30 (Engl. Transl.)].Google Scholar

Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • M. M. Krayushkin
    • 1
  • M. A. Kalik
    • 1
  • S. A. Voznesensky
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations