A convenient synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-assisted grinding. Issue 29 (20th July 2016)

• Record Type: Journal Article
• Authors: Pattarawarapan, Mookda; Jaita, Subin; Phakhodee, Wong
• Is Part Of: Tetrahedron letters. Volume 57:Issue 29(2016)
• Page Start: 3171
• Page End: 3174
• Publication Date: 2016-07-20
• Subjects: Hippuric acid -- Cyanuric chloride -- Triphenylphosphine -- Azlactones -- Mechanosynthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.029
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The TCT-mediated synthesis of Erlenmeyer azlactones is reported. Condensation of hippuric acid with aromatic aldehydes proceeded rapidly. The products were afforded in high yields without column chromatography. Abstract: A facile and effective approach for the synthesis of 4-arylidene-2-phenyl-5(4 H )-oxazolones has been developed. Under solvent-assisted grinding in the presence of 2, 4, 6-trichloro-1, 3, 5-triazine, catalytic triphenylphosphine, and sodium carbonate, dehydration–condensation of hippuric acid with aromatic aldehydes proceeded rapidly within minutes at room temperature to afford the products in good to excellent yields.