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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;
Further Information

Publication History

Received 6 December 2002
Publication Date:
07 March 2003 (online)

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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

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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.