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Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives

Abstract

Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, {sup 1}H-and {sup 13}C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P.  More>>
Authors:
Elhadi, S A [1] 
  1. Department of Chemistry, Faculty of Education, University of Khartoum, Khartoum (Sudan)
Publication Date:
Sep 01, 2004
Product Type:
Thesis/Dissertation
Report Number:
INIS-SD-273
Resource Relation:
Other Information: 80 refs., 28 tabs., app 23,. scheme 7
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; CHEMICAL ANALYSIS; CHEMICAL PREPARATION; CHROMATOGRAPHY; IMPURITIES; INFRARED SPECTRA; MOLECULAR STRUCTURE; NUMERICAL DATA; ORGANIC COMPOUNDS; QUINOLINES; SPECTROSCOPY; SUDAN; SYNTHESIS
OSTI ID:
20655571
Research Organizations:
University of Khartoum, Khartoum (Sudan)
Country of Origin:
Sudan
Language:
English
Other Identifying Numbers:
TRN: SD0500023095257
Availability:
Available from INIS in electronic form; Also available from Sudan Atomic Energy Commisson, Khartoum (SD)
Submitting Site:
INIS
Size:
141 pages
Announcement Date:
Dec 01, 2005

Citation Formats

Elhadi, S A. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives. Sudan: N. p., 2004. Web.
Elhadi, S A. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives. Sudan.
Elhadi, S A. 2004. "Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives." Sudan.
@misc{etde_20655571,
title = {Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives}
author = {Elhadi, S A}
abstractNote = {Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, {sup 1}H-and {sup 13}C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl -6-sulphanilamide-quinolin-4-carboxylic acid showed the highest activity against the four standard tested organisms.(Author)}
place = {Sudan}
year = {2004}
month = {Sep}
}