Download PDF
Synlett 2002(3): 0513-0515
DOI: 10.1055/s-2002-20482
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Improved Synthesis of Pyrazolines from Aryl Azides and Acrylic Esters [1]

J. S. Yadav*, B. V. Subba Reddy, V. Geetha
Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)7170512; e-Mail: yadav@iict.ap.nic.in;
Further Information

Publication History

Received 4 January 2002
Publication Date:
05 February 2007 (online)

    Permissions and Reprints All articles of this category

Abstract

Substituted pyrazoline derivatives are synthesized in high yields through the cycloaddition reactions of azides with acrylates under Baylis-Hillman reaction conditions. Improved yields and enhanced rates are obtained using DABCO as the base.

Key words

azides - Baylis-Hillman reaction - cycloaddition reactions - pyrazolines

1

IICT Communication No. 4826.

    References

  • 2 Holmwood G, Buechel KH, Reinecke P, Brandes W, and Haenssler G. inventors; German patent  3510411.  ; Chem. Abstr. 1987, 106, 14714e
  • 3 Inke SA. inventors; Spanish patent  548092.  ; Chem. Abstr. 1987, 106, 67321f
  • 4 Luethy C, and Zurflueh R. inventors; European patent  202321.  ; Chem. Abstr. 1987, 106, 138455r
  • 5a Patai S. The Chemistry of the Azide Group   Interscience publishers; New York: 1971.  p.331-383  
    CrossrefGoogle Scholar
  • 5b Gilchrist TL. Gymer GE. Katritzky AR. Boulton JA. Adv. Heterocycl. Chem.  1974,  16:  33 
    CrossrefGoogle Scholar
  • 5c Borello E. Zecchina A. Gulielminotti E. J. Chem. Soc. B  1969,  307 
    CrossrefGoogle Scholar
  • 6 Finely KT. In The Chemistry of Heterocyclic Compounds   Weissberger A. Talor EC. John Wiley and Sons; New York NY: 1980.  p.1-63  
    Google Scholar
  • 7 Abu-Orabi ST. Atfah MA. Jibril I. Mari FM. A-Sheikh Ali A. J. Heterocycl. Chem.  1989,  26:  1461 
    CrossrefGoogle Scholar
  • 8 Huisgen R. Szeimies G. Mobius L. Chem. Ber.  1966,  99:  475 
    CrossrefGoogle Scholar
  • 9 Broeckx W. OverBergh N. Samyn C. Smets G. Labbe G. Tetrahedron  1971,  27:  3534 
    Google Scholar
1

IICT Communication No. 4826.