Utility of the Pfitzinger Reaction in the Synthesis of Novel Quinoline Derivatives and Related Heterocycles

Gok D., KASIMOĞULLARI R., Cengiz M., Mert S.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.51, no.1, pp.224-232, 2014 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 51 Issue: 1
  • Publication Date: 2014
  • Doi Number: 10.1002/jhet.1607
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.224-232


2-(2-Amino-3,5-dinitrophenyl)-2-oxoacetic acid (2) was obtained from hydrolysis of 5,7-dinitroisatin (1) in alkaline media. A novel quinoxaline derivative (3) was synthesized from the reaction of the same compound (1) with o-phenylenediamine. Reacting 2 with ethyl 3-oxo-3-phenylpropanoate yields 6,8-dinitro-2-phenylquinoline-3,4-dicarboxylic acid (4). Then, 4 was converted into new quinoline-diacylchloride, quinoline-ester, quinoline-dicarboxamide, pyridazine, and pyrroledione derivatives (5, 6a, 6b, 6c, 6d, 7a, 7b, 7c, 7d, 8, 9, 10a, 10b, 10c, 10d, 11a, 11b, 12) with SOCl2, alcohols, amines, and hydrazines, respectively. The structures of synthesized compounds were clarified by H-1 NMR, C-13 NMR, IR, mass and elemental analysis methods.