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

• Published in: Research on chemical intermediates Vol. 41; no. 12; pp. 10109 - 10123
• Main Authors: Escobar, Angélica M., Ruiz, Diego M., Autino, Juan C., Romanelli, Gustavo P.
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01-12-2015
• Subjects: Catalysis; Chemistry; Chemistry and Materials Science; Inorganic Chemistry; Physical Chemistry; Preyssler catalyst; Recyclable catalyst; 4-Dihydrocoumarins; 4-Phenyl-3; 4-Phenylcoumarins; Solvent-free reaction conditions
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-015-2016-3

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