Synthesis of new 6-substituent 2-phenyl and 2-(furan-2-yl)-3-phenyl-quinoline-4-carboxylic acid derivatives

Abstract

A synthesis of substituted quinolines has been achieved by the Doebner reaction which is a three component coupling of arylaldehyde, p-amino-acetophenone and phenyl pyruvic acid. The products of 2,3-diary-6-acetyl-quinoline-4-carboxylic acids were obtained by Claisen Schmidt condensation reaction with aldehydes in the presence of sodium hydroxide in order to give the corresponding α,β-unsaturated carbonyls. The substituted α,β-unsaturated carbonyls were condensed with urea, thiourea, hydrazine, phenyl hydrazine, semicarbazide hydrochloride and ethanolamine to synthesized 2-pyrimidinone, 2-pyrimidinethion, pyrazoline-1-phenyl, pyrazoline, pyrazoline-1-carboxamide and 1,4-oxazepines derivatives, respectively, with good yields. The purity and identities of products were elucidated through thin layer chromatography (TLC), melting point and spectroscopic data (IR, 1H NMR, 13C NMR and LC-Mass).

Synthesis of quinolinesviasequential addition and I2-mediated desulfurative cyclization

“…6 Since that, extensive attention has been paid to the synthesis of quinolines and their derivatives for their broad range of pharmaceutical activity, such as anti-viral, anti-cancer and anti-HIV. 7–9 Various synthetic transformations have been developed to obtain quinolines, including Combes synthesis, 10–12 Skraup reaction, 13 Conrad–Limpach synthesis, 14–16 Povarov reaction, 17,18 Doebner reaction, 19,20 Doebner–Miller reaction, 21–23 Gould–Jacobs reaction, 24,25 Friedländer reaction, 26–29 and so on. However, considering the extreme significance of quinoline derivatives, the development of mild and economic approaches is still attractive.…”