Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H 14 P 5 NaW 30 O 110 ) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 °C, in...

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Veröffentlicht in:Research on chemical intermediates 2015-12, Vol.41 (12), p.10109-10123
Hauptverfasser: Escobar, Angélica M., Ruiz, Diego M., Autino, Juan C., Romanelli, Gustavo P.
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Sprache:eng
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Zusammenfassung:4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H 14 P 5 NaW 30 O 110 ) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 °C, in a short reaction time (2 h). Under these conditions, very good yields (11 examples: 61 %–90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton. Graphical abstract
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-015-2016-3