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A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica–alumina supported heteropolyacids

Paper ID Volume ID Publish Year Pages File Format Full-Text
43171 45957 2009 6 PDF Available
Title
A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica–alumina supported heteropolyacids
Abstract

Eleven examples of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride was added to the hot solution as a dehydrating agent. Molybdophosphoric or tungstophosphoric acids supported on silica–alumina, obtained by the sol–gel method, catalyze the reaction. The prepared catalysts were characterized by X-ray diffraction and diffuse reflectance spectroscopy. The specific surface area of the catalysts was determined by the nitrogen adsorption/desorption at 196 °C technique, and the catalyst acidity was measured by potentiometric titration with n-butylamine. The heteropolyacid amount removed from the catalysts during the leaching with toluene was lower than 1%. The products were obtained with high conversion and selectivity. The yields were in the 87–96% range for the majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70–80% range. The same catalysts were used several times without appreciable loss of their catalytic activity. A rational mechanism for the azlactone formation catalyzed by the supported heteropolyacid is proposed.

Graphical abstractAzlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride. The reaction was catalyzed by molybdophosphoric or tungstophosphoric acids supported on silica–alumina. The yields were in the 87–96% range for majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70–80% range. Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Azlactones; Catalysis; Condensation; Cyclodehydration; Keggin heteropolyacids; Oxazolones
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A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica–alumina supported heteropolyacids
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 352, Issues 1–2, 15 January 2009, Pages 208–213
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
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Online Support
Any Questions? feel free to contact us