Design, Synthesis, and Characterization of Tautomeric Quinoline-4-Carboxylic Acid–Based Esters, Amides, and Fused Heterocycles Derviş Gök Journal of Chemistry, 2026 Quinoline‐4‐carboxylic acid derivatives are widely studied owing to their structural versatility and relevance in pharmaceutical sciences. In this study, 3‐benzoyl‐2‐oxo‐1,2‐dihydroquinoline‐4‐carboxylic acid was synthesized via a solvent‐free reaction between ethyl 3‐oxo‐3‐phenylpropanoate and sodium 2‐(2‐aminophenyl)‐2‐oxoacetate. Two distinct tautomeric forms of the product were identified, offering opportunities for further derivatization. New quinoline ester derivatives were obtained by reacting the open‐form tautomer with various alcohols. The corresponding quinoline amide derivatives were synthesized via the reaction of 3‐benzoyl‐2‐oxo‐1,2‐dihydroquinoline‐4‐carbonyl chloride, obtained by the reaction between 3‐benzoyl‐2‐oxo‐1,2‐dihydroquinoline‐4‐carboxylic acid and SOCl 2 , with ammonia, hydrazine, and various aromatic primary amines. The cyclization of the hydrazine‐derived quinoline amide derivative yielded the pyridazino[4,5‐c]quinoline derivative. Furthermore, a series of novel pyrrolo[3,4‐c]quinoline derivatives were synthesized via Schiff base reactions between various primary amines and the ketone‐containing 3‐benzoyl‐2‐oxo‐1,2‐dihydroquinoline‐4‐carboxylic acid. Hence, a diverse group of quinoline‐4‐carboxylic acid derivatives, including pyridazino, pyrrolo, amide, and ester derivatives, was successfully synthesized using optimized procedures. All synthesized compounds were thoroughly characterized, and their structures were confirmed by infrared spectroscopy, mass spectrometry, and proton and carbon‐13 nuclear magnetic resonance spectroscopy. These findings contribute to the development of structurally novel heterocyclic frameworks and may serve as valuable platforms for future drug discovery and medicinal chemistry applications.
One-pot three-component synthesis of novel 2-(3-nitro-phenyl)-quinazoline-4-carboxylic acid derivatives Dervis Gok Journal of Heterocyclic Chemistry, 2019 A simple and easy synthesis of 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carboxylic acid (3) has been successfully developed through a one‐pot three‐component condensation reaction of (2‐amino‐phenyl)‐oxo‐acetic acid sodium salt (1) obtained from the hydrolysis of isatin with ammonium acetate and 3‐nitrobenzaldehyde. Some novel quinazoline‐ester derivatives 4‐7 were then obtained by the reaction between the new compound 3 and various alcohols. Then, quinazoline‐amide derivatives 10‐14 were synthesized from the reaction of various amines and 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carbonyl chloride (8), obtained by the reaction of compound 3 with SOCl2. Finally, some novel quinazoline‐azo derivatives 17‐19 were synthesized by the coupling reaction between β‐dicarbonyl compounds and the novel amino‐quinazoline derivative compound 15, obtained by reduction of nitro‐quinazoline derivative compound 11. Thus, a new series of quinazoline‐4‐carboxylic acid, ester, amide, and azo derivatives was synthesized and fully characterized by 1H NMR, 13C NMR, IR, and mass spectrometry analysis.
Utility of the pfitzinger reaction in the synthesis of novel quinoline derivatives and related heterocycles Derviş Gök, Rahmi Kasımoğulları, Mustafa Cengiz, Samet Mert Journal of Heterocyclic Chemistry, 2014 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.