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 |
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Hauptverfasser: | , , , |
Format: | Artikel |
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 |
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ISSN: | 0922-6168 1568-5675 |
DOI: | 10.1007/s11164-015-2016-3 |