Intramolecular Baylis-Hillman Reaction: A Pathway to Substituted Coumarins

Siegfried E. Drewes Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa

Owen L. Njamela Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa

Neville D. Emslie Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa

Niyum Ramesar Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa

John S. Field Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa

Abstract

The acrylate ester of salicylaldehyde, in the presence of DABCO, affords a crystalline coumarin salt. Formation of this derivative confirms a vital intermediate in the mechanism of the reaction. Salicylaldehyde, suitably protected, reacts with methyl acrylate to afford a novel coumarin not unlike the vasodilator chromonar.

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Intramolecular Baylis-Hillman Reaction: A Pathway to Substituted Coumarins

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Intramolecular Baylis-Hillman Reaction: A Pathway to Substituted Coumarins

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