Synthesis of new 5-oxazolones: Their ring opening reactions to obtain new benzamide derivatives

Omer Tahir Gunkara; Muge Guleli; Senem Akkus Cevikkalp; Kerem Kaya; Nuket Ocal

doi:10.2174/1570179413666161031164124

Synthesis of new 5-oxazolones: Their ring opening reactions to obtain new benzamide derivatives

Omer Tahir Gunkara^*
, Muge Guleli
, Senem Akkus Cevikkalp
, Kerem Kaya
, Nuket Ocal

^*Corresponding author for this work

Department of Chemistry

Yildiz Technical University
Scientific and Technological Research Council of Turkey
Gebze Technical University

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	283-290
Number of pages	8
Journal	Current Organic Synthesis
Volume	14
Issue number	2
DOIs	https://doi.org/10.2174/1570179413666161031164124
Publication status	Published - 1 Mar 2017

Bibliographical note

Publisher Copyright:
© 2017 Bentham Science Publishers.

Keywords

5-oxazolone
Benzamides
Biological activity
Heterocycles
Nucleophilic attack
Ring opening reactions

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10.2174/1570179413666161031164124

Cite this

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title = "Synthesis of new 5-oxazolones: Their ring opening reactions to obtain new benzamide derivatives",

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 = "5-oxazolone, Benzamides, Biological activity, Heterocycles, Nucleophilic attack, Ring opening reactions",

author = "Gunkara, \{Omer Tahir\} and Muge Guleli and Cevikkalp, \{Senem Akkus\} and Kerem Kaya and Nuket Ocal",

note = "Publisher Copyright: {\textcopyright} 2017 Bentham Science Publishers.",

year = "2017",

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doi = "10.2174/1570179413666161031164124",

language = "English",

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TY - JOUR

T1 - Synthesis of new 5-oxazolones

T2 - Their ring opening reactions to obtain new benzamide derivatives

AU - Gunkara, Omer Tahir

AU - Guleli, Muge

AU - Cevikkalp, Senem Akkus

AU - Kaya, Kerem

AU - Ocal, Nuket

PY - 2017/3/1

Y1 - 2017/3/1

N2 - 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.

AB - 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.

KW - 5-oxazolone

KW - Benzamides

KW - Biological activity

KW - Heterocycles

KW - Nucleophilic attack

KW - Ring opening reactions

UR - https://www.scopus.com/pages/publications/85013944451

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DO - 10.2174/1570179413666161031164124

M3 - Article

AN - SCOPUS:85013944451

SN - 1570-1794

VL - 14

SP - 283

EP - 290

JO - Current Organic Synthesis

JF - Current Organic Synthesis

IS - 2

ER -

Synthesis of new 5-oxazolones: Their ring opening reactions to obtain new benzamide derivatives

Abstract

Bibliographical note

Keywords

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