Utility of the Pfitzinger Reaction in the Synthesis of Novel Quinoline Derivatives and Related Heterocycles |
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Authors: | Dervi? Gök Rahmi Kas?mo?ullar? Mustafa Cengiz Samet Mert |
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Institution: | 1. Department of Chemistry and Chemical Processing Technologies, Kutahya Vocational School, Dumlupinar University, Kutahya, Turkey;2. Department of Chemistry, Faculty of Arts and Sciences, Dumlupinar University, Kutahya, Turkey;3. Department of Chemistry, Faculty of Arts and Sciences, Suleyman Demirel University, Isparta, Turkey |
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Abstract: | 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 1H NMR, 13C NMR, IR, mass and elemental analysis methods. |
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