A New Method for the Synthesis of Substituted Quinolines by the Reaction of Acrylonitrile and Substituted Phenyl Schiff Base

Abstract

The invention relates to a new method for synthesis of substituted quinoline through reaction of acrylonitrile and substituted phenyl Schiff base. The method includes: adding substituted phenyl Schiff base and acrylonitrile in a mole ratio of 1:1.1 into a reaction container containing glacial acetic acid, stirring them uniformly, conducting heating and heat preservation on the reaction solution till the end of the reaction, evaporating the acetic acid, and then subjecting the residue to thin layer chromatography so as to obtain the substituted quinoline. The method provided in the invention solves the defects of strict requirements for substrates, inconvenient product separation and purification, applicability to preparation of only special structure quinoline derivatives, difficult separation and recovery of transition metal catalysts and heavy metal drug residue and the like in previous methods. The method involved in the invention has the advantages of simple operation, molecular economy, low energy consumption, and highest product yield.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a new method for synthesizing substituted quinolines by reacting acrylonitrile and substituted phenyl Schiff bases. Background technique [0002] The quinoline ring structure widely exists in natural products and synthetic drugs, and this type of compound is one of the most important drug classes in the history of antimalarials. In recent years, with the in-depth research on heterocyclic drugs, especially the research on the synthesis of various substituted quinoline molecules and their physiological activities, the application of substituted quinolines in medicine has attracted more and more attention. . Such molecules have good prospects for drug development. [0003] Prior to the present invention, the existing quinoline compounds were prepared by extraction from coal tar or synthesis by catalytic chemical methods. Due to the low content and single species in coa...

AI Technical Summary

Problems solved by technology

The preparation of quinoline by Baylis-Hillman synthesis is rarely used in organic synthesis, mainly because of strict requirements on substrates, and the separation and purification of products is very inconvenient, so it is only suitable for the preparation of quinoline derivatives with special structures

In recent years, it has been reported that transition metals can be used as acid catalysts to synthesize quinoline derivatives, but transition metal catalysts still have problems such as separation and recovery difficulties and heavy metal drug residues, which are not suitable for wide application.

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