Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 4, Pages 827-830Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100039
Keywords
annulation; β -keto ester; chromones; oxygen heterocycles; transesterification
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIT) [2018R1A2B2004432, 2021R1A2B5B02002436]
- Korean Ministry of Education, Science, and Technology [2012M3A7B4049677]
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A mild base-promoted reaction between 3-substituted chromones and beta-keto esters is described for the easy access to various coumarins. The protocol provides highly functionalized 3-acyl-4-arylcoumarins in good-to-excellent yield via benzannulation and transesterification, with a proposed reaction mechanism involving Michael addition, 1,5-H shift, and intramolecular transesterification.
A mild base-promoted reaction between 3-substituted chromones and beta-keto esters for the easy access to various coumarins with structural diversity is described. This protocol provides highly functionalized 3-acyl-4-arylcoumarins in good-to-excellent yield via benzannulation and transesterification. A reaction mechanism containing Michael addition, 1,5-H shift and intramolecular transesterification is proposed.
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