One-pot synthesis of functionalized benzo[c]coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins

2-(Polyfluoroalkyl)chromones react with 4-alkyl-3-cyanocoumarins in dichloromethane in the presence of triethylamine to give a wide variety of functionalized benzo[ c ]coumarin derivatives in good yields. This new annulation reaction presumably proceeds by a tandem intermolecular Michael addition an...

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Bibliographic Details
Published in:RSC advances 2016, Vol.6 (63), p.58188-58202
Main Authors: Sosnovskikh, Vyacheslav Ya, Korotaev, Vladislav Yu, Kutyashev, Igor B., Barkov, Alexey Yu, Safrygin, Alexander V.
Format: Article
Language:English
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Summary:2-(Polyfluoroalkyl)chromones react with 4-alkyl-3-cyanocoumarins in dichloromethane in the presence of triethylamine to give a wide variety of functionalized benzo[ c ]coumarin derivatives in good yields. This new annulation reaction presumably proceeds by a tandem intermolecular Michael addition and subsequent intramolecular condensation between an intermediate enolate anion and cyano group. In the case of 3-cyano-4-methylcoumarin and 2-(trifluoromethyl)chromones activated by two electron-withdrawing substituents, three acyclic intermediates were isolated and the possible mechanism of the reaction was suggested.
ISSN:2046-2069
2046-2069
DOI:10.1039/C6RA12492E