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

作者:Gok Dervis; Kasimogullari Rahmi*; Cengiz Mustafa; Mert Samet
来源:Journal of Heterocyclic Chemistry, 2014, 51(1): 224-232.
DOI:10.1002/jhet.1607

摘要

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.

  • 出版日期2014-1

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