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

[ Vol. 14 , Issue. 2 ]

Author(s):

Omer Tahir Gunkara*, Muge Guleli, Senem Akkus Cevikkalp, Kerem Kaya and Nuket Ocal   Pages 283 - 290 ( 8 )

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.

Affiliation:

Chemistry Department, Faculty of Science and Arts, Yildiz Technical University, Davutpasa Campus, Istanbul, Chemistry Department, Faculty of Science and Arts, Yildiz Technical University, Davutpasa Campus, Istanbul, TUBITAK MAM, 41470 Kocaeli, Department of Chememistry, Faculty of Science and Letters, Istanbul Technical University, Istanbul, Gebze Technical University, Department of Chemistry, Faculty of Science, POB 141, TR 41400, Gebze, Kocaeli

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