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

GÜNKARA Ö. T., GULELI M., CEVIKKALP S. A., Kaya K., Ocal N.

CURRENT ORGANIC SYNTHESIS, vol.14, no.2, pp.283-290, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 2
  • Publication Date: 2017
  • Doi Number: 10.2174/1570179413666161031164124
  • Journal Name: CURRENT ORGANIC SYNTHESIS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.283-290
  • Keywords: Benzamides, biological activity, heterocycles, nucleophilic attack, 5-oxazolone, ring opening reactions, ACID, INHIBITORS, RESOLUTION, MECHANISM
  • Yıldız Technical University Affiliated: Yes

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, H-1, C-13 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.