Synlett 2003(11): 1746-1748
DOI: 10.1055/s-2003-41436
LETTER
© Georg Thieme Verlag Stuttgart · New York

Molecular Sieve (MS 4A) Promoted Cyclocondensation of Hindered, Aromatic Nitrile Oxides and Cyclic Diketones under Mild Conditions

Tomoo Matsuura, Jeffrey W. Bode, Yoshifumi Hachisu, Keisuke Suzuki*
Department of Chemistry, Tokyo Institute of Technology and CREST, Japan Science and Technology Corporation, O-okayama, Meguro-ku, Tokyo 152-8551, Japan
Fax: +81(3)57342228; e-Mail: ksuzuki@chem.titech.ac.jp;
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Publikationsverlauf

Received 6 June 2003
Publikationsdatum:
22. September 2003 (online)

Abstract

Molecular sieves (MS 4A) serve as efficient promoters for the cyclocondensation of stable, hindered nitrile oxides and a variety of cyclic diketones to afford fused isoxazoles in good yield. The operational simplicity and remarkably mild reaction conditions compliment our amine-promoted cyclocondensation conditions and demonstrate broad substrate scope.

    References

  • 1a Bode JW. Hachisu Y. Matsuura T. Suzuki K. Tetrahedron Lett.  2003,  44:  3555 
  • 1b Bode JW. Hachisu Y. Matsuura T. Suzuki K. Org. Lett.  2003,  5:  391 
  • 2 For a review of molecular sieve and zeolite promoted reactions, see: Sen SE. Smith SM. Sullivan KA. Tetrahedron  1999,  55:  12657 
  • 3 The use of 4 Å MS as a base for the elimination of C-chloroximes to form nitrile oxides and subsequent cycloaddition with acrylates has been reported. However, under these conditions long reaction times (7-10 d) were necessary, see: Kim JN. Ryu EK. Heterocycles  1990,  31:  1693 
  • 5 Thermal cycloadditions of 2-hydroxynaphthoquinone and nitrile oxides have been previously reported: Brahmeshwari G. Rao VR. Rao TVP. Indian J. Chem., Sect. B  1995,  34:  139 
  • 6 Bode JW. Suzuki K. Org. Lett.  2003,  5:  394 
  • 7 Hachisu Y. Bode JW. Suzuki K. J. Am. Chem. Soc.  2003,  125:  8432 
  • 8 Bode JW. Suzuki K. Tetrahedron Lett.  2003,  44:  3559 
  • 9 For a Diels-Alder type cycloaddition reaction promoted by molecular sieves, see: Pindur U. Haber M. Heterocycles  1991,  32:  1463 
4

MS 4A have the general formula Na2O·Al2O3·xSiO2·yH2O.