Intramolecular Baylis-Hillman Reaction: A Pathway to Substituted Coumarins
- 1 November 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (20) , 2807-2815
- https://doi.org/10.1080/00397919308012600
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.Keywords
This publication has 8 references indexed in Scilit:
- An intramolecular Baylis-Hillman reactionTetrahedron Letters, 1992
- The ‘Baylis - Hillman Reaction’ mechanism and applications revisitedTetrahedron, 1992
- A kinetic and mechanistic study of the Baylis-Hillman reactionTetrahedron Letters, 1991
- Functionalisation of the α position of acrylate systems by the addition of carbonyl compounds: Highly pressure-dependent reactions.Tetrahedron Letters, 1986
- DABCO-catalyzed coupling of aldehydes with activated double bonds. 4. Stereoselective synthesis of trisubstituted olefins and terpenoid building blocks via 2-(hydroxyalkyl)-2-propenoic estersThe Journal of Organic Chemistry, 1985
- Preparation of 2‐(1‐Hydroxyalkyl)acrylic Esters; Simple Three‐Step Synthesis of Mikanecic AcidAngewandte Chemie International Edition in English, 1983
- Necic acid synthons. Part 1. Total synthesis of integerrinecic acidJournal of the Chemical Society, Perkin Transactions 1, 1982
- Ortho lithiation via a carbonyl synthonThe Journal of Organic Chemistry, 1979