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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

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 and Nuket Ocal

Volume 14, Issue 2, 2017

Page: [283 - 290] Pages: 8

DOI: 10.2174/1570179413666161031164124

Price: $65

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.

Graphical Abstract

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