PDF herunterladen
Synthesis 2003(4): 0531-0534
DOI: 10.1055/s-2003-37655
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient and Chemoselective Access to 3-(Chloromethyl)coumarins via Direct Cyclisation of Unprotected Baylis-Hillman Adducts

Perry T. Kaye*, Musiliyu A. Musa, Xolani W. Nocanda
Department of Chemistry, Rhodes University, Grahamstown, 6140, South Africa
Fax: +27(46)6225109; e-Mail: P.Kaye@ru.ac.za;
Weitere Informationen

Publikationsverlauf

Received 6 December 2002
Publikationsdatum:
07. März 2003 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Reaction of substituted 2-hydroxybenzaldehydes with t-butyl acrylate in the presence of DABCO has been shown to afford isolable Baylis-Hillman adducts, acid-catalysed cyclisation of which affords the corresponding 3-(chloromethyl)coumarins directly and in high yield.

Key words

heterocycles - synthesis - coumarins - 2H-1-benzopyran-2-ones - Baylis-Hillman reaction

    References

  • 1 Murray RDH. In Progress in the Chemistry of Natural Products   Herz W. Grisebach H. Kirby GW. Springer-Verlag; New York: 1978.  p.199-429  
    Google Scholar
  • 2 Jeanneret V. Vogel P. Renaut P. Millet J. Theveniaux J. Barberousse V. Bioorg. Med. Chem. Lett.  1998,  8:  1687 
    CrossrefGoogle Scholar
  • 3 Musiciki B. Periers A.-M. Laurin P. Ferroud D. Benedetti Y. Lachaud S. Chatreaux F. Haesslein J.-L. Iltis A. Pierre C. Khider J. Tessot N. Airault M. Demassey J. Dupuis-Hamelin C. Lassaigne P. Bonnefoy A. Vicat P. Klich M. Bioorg. Med. Chem. Lett.  2000,  10:  1695 
    CrossrefGoogle Scholar
  • 4 Takeuchi Y. Xie L. Cosentino LM. Lee K.-H. Bioorg. Med.Chem. Lett.  1997,  7:  2573 
    Google Scholar
  • 5a John EVO. Israelstam SS. J. Org. Chem.  1961,  26:  240 
    Google Scholar
  • 5b Panetta JA. Rapoport H. J. Org. Chem.  1982,  47:  946 
    Google Scholar
  • 5c Mali RS. Yadav VJ. Synthesis  1977,  464 
    Google Scholar
  • 5d Hepworth JD. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Boulton AJ. McKillop A. Pergamon; Oxford: 1984.  p.881 
    Google Scholar
  • 5e Bogdal D. J. Chem. Res., Synop.  1998,  468 
    Google Scholar
  • 5f Fall Y. Terán C. Teijeira M. Santana L. Uriarte E. Synthesis  2000,  643 
    Google Scholar
  • 5g Fall Y. Santana L. Teijeira M. Uriarte E. Heterocycles  1995,  41:  647 
    Google Scholar
  • 7 Kaye PT. Musa MA. Synthesis  2002,  2701 
    Artikel in Thieme ConnectGoogle Scholar
  • 9a Kaye PT. Robinson RS. Synth. Commun.  1996,  26:  2085 
    Google Scholar
  • 9b Bacsa J. Kaye PT. Robinson RS. S. Afr. J. Chem.  1998,  51:  47 
    Google Scholar
  • 10 Musa MA. PhD Thesis   Rhodes University; South Africa: 2002. 
    Google Scholar
  • 11 Drewes SE. Roos GHP. Tetrahedron  1988,  44:  4653 
    CrossrefGoogle Scholar
  • 12 Satoh Y. Stanton JL. Hutchison AJ. Libby AH. Kowalski TJ. Lee WH. White DH. Kimble EF. J. Med. Chem.  1993,  36:  3580 
    CrossrefGoogle Scholar
  • 13 Hochrainer A. Wessely F. Tetrahedron Lett.  1965,  721 
    CrossrefGoogle Scholar
6

Kaye, P. T.; Musa, M. A. Synth. Commun., in press.

8

In our own studies unprotected Baylis-Hillman adducts of this type have only been isolated as minor products in reactions of protected substrates.

14

Nominal m/z values from HRMS analysis.