Journal
TETRAHEDRON LETTERS
Volume 75, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153206
Keywords
Chromones; Enol ester; 4-Hydroxy coumarin; Silver catalysis; Deacetylation
Categories
Funding
- SERB, Government of India [EMR/2017/002827]
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A silver-catalyzed aerobic approach has been developed for the synthesis of 2-methyl-chromone-3-carboxylic acid from the reaction of 4-hydroxy coumarin and enol ester in the presence of base. Mechanistic investigation suggests that the key steps for the overall transformation include the base induced Michael-type addition reaction and sequential ring opening and closing with the liberation of acetone. Theoretical calculation of energy of the intermediates by DFT supports the proposed reaction mechanism.
A silver-mediated aerobic approach to access 2-methyl-chromone-3-carboxylic acid from the reaction of 4-hydroxy coumarin and enol ester in the presence of base has been presented. Mechanistic investigation suggests that the base induced Michael-type addition reaction of 4-hydroxy coumarin to the enol ester resulting the sequential ring opening and closing with the liberation of acetone are the key-steps for the overall transformation. Theoretical calculation of energy of the intermediates by DFT supports the proposed reaction mechanism. (C) 2021 Elsevier Ltd. All rights reserved.
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