A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2H-1-benzopyran-2-ones

Perry T. Kaye; Musiliyu A. Musa

doi:10.1055/s-2002-35984

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Synthesis 2002(18): 2701-2706
DOI: 10.1055/s-2002-35984

PAPER

A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2H-1-benzopyran-2-ones

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

Further Information

Publication History

Received 9 September 2002
Publication Date:
06 December 2002 (online)

Abstract
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Abstract

Halogen acid-catalysed deprotection and cyclisation of Baylis-Hillman products obtained using O-benzylated salicylaldehyde precursors has been shown to afford 3-(halomethyl)coumarins (3-halomethyl-2H-1-benzopyran-2-ones) chemoselectively and in good yield.

Key words

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

References

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Kaye, P.T.; Musa, M.A. Synth. Commun., in press (SC-2002-051).

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Athough an allylic displacement (S_N′) pathway cannot be excluded, there are some precedents for the addition-elimination sequence outlined in Scheme [2] . See Ref. [15] for further comment.