Synthesis of New 5-Oxazolones: Their Ring Opening Reactions to Obtain New Benzamide Derivatives

Author(s): Omer Tahir Gunkara*, Muge Guleli, Senem Akkus Cevikkalp, Kerem Kaya, Nuket Ocal

Journal Name: Current Organic Synthesis

Volume 14 , Issue 2 , 2017

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Graphical Abstract:


New 5-oxazolones have been synthesized via N-protected amino acids which were prepared from various aryl acyl halides and L-amino acids, with DCC. Then, we studied the ring opening reactions of 5-oxazolones with nucleophilic attack by primary aryl amines to obtain new racemic benzamide derivatives. All new synthesized compounds have been characterized by FTIR, 1H, 13C NMR, GC/MS, LC/MS and Qtof analyses. X-Ray results of N-(1-((4-chlorophenyl)amino)-3-methyl-1-oxopentan-2-yl)-3-(trifluoromethyl)benzamide clearly showed absolute stereostructure.

Keywords: Benzamides, biological activity, heterocycles, nucleophilic attack, 5-oxazolone, ring opening reactions.

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Article Details

Year: 2017
Page: [283 - 290]
Pages: 8
DOI: 10.2174/1570179413666161031164124
Price: $65

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