Study On Synthesis Of Quinoline Derivatives

Quinoline and its derivatives, which play an important role in the field of drugfiltration, chemical analysis, dye industry, etc., are important organic heterocycle.Therefore, since the beginning of the last century, chemists found that the synthesismethod of quinoline, how to use the chemical methods to synthesize quinoline and itsderivatives has been the focus of synthetic organic chemistry. Classical organicsynthesis of quinoline derivatives usually used aniline compounds as the startingmaterial with α, β-unsaturated aldehyde or ketone or its derivatives, occurredthe Michael addition, cyclization, dehydrogenation, and a series of reactions to thesynthesis of quinoline derivatives. However, these reactions are usually carriedout under high temperature, strongly acidic conditions, which had some shortcomingssuch as environmental pollution, highly equipment requirements.Although the transition metal catalyzed synthesis method is effective to avoidthe high temperatures and strong acids, the transition metal catalyst still exists a seriesof deficiencies such as catalyst separation and recycling difficulties in the catalyticreaction process. Therefore, the study of the new atom economy, green syntheticmethod of quinoline and its derivatives is of great significance.In this paper, we study and completed a novel method for synthesis quinoline andits derivatives.(1) Substituted o-nitrotoluene derivatives reacted with acrylic estersunder the mild condition and base-catalyzed forming the quinolin-2-carboxylic acidester derivatives;(2) Substituted o-nitrotoluene derivatives reacted with acrylonitrileunder the mild condition and base-catalyzed forming the quinolin-2-carbonitrilederivatives;(3) Substituted o-nitrotoluene derivatives reacted with Methacrylate underthe mild condition and base-catalyzed forming the2-methyl-1,2,3,4-tetrahydro--quinoline-2-carboxylic acid ester derivatives. At the same time, we discuss a numberof aspects of the reaction, such as solvents, the amounts of the base, reactiontemperature, reaction time and so on; Also discussed the mechanism of the reaction.The synthesis of a series of new quinoline derivatives was characterized andanalyzed by HRMS, IR,1HNMR,13CNMR and X-Ray diffraction.The reagents used in this paper basically no toxicity, in line with the requirement--s of modern society to promote green chemistry and environmental chemistry,which offers both theoretical and experimental basis for studying new quinoline derivatives.