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Synlett 2003(11): 1746-1748
DOI: 10.1055/s-2003-41436
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
Weitere Informationen
Received
6 June 2003
Publikationsdatum:
22. September 2003 (online)
Publikationsverlauf
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.
Key words
cycloadditions - ketones - condensation - isoxazoles - molecular sieves
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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
References
MS 4A have the general formula Na2O·Al2O3·xSiO2·yH2O.