Довголанцюгові основи Шиффа на основі хіноліну

Abstract

Azomethines with heterocyclic fragment in its composition are used as pigments of dyes, catalysts, intermediates in organic synthesis and as stabilizers in the production of high molecular weight compounds. Known examples of using Schiff bases to obtain transition metal complexes what are important for analytical chemistry. Also, azomethines show a wide range of biological activity: they exhibit anti-inflammatory, anti-fungal, antibacterial and anticonvulsant activity.The introduction of a quinoline cycle to the azomethine moiety may increase the bioactivity of the latter, as it is known that functional quinoline derivatives exhibit a wide range of biological activity. The purpose of this work is to synthesize new azomethines based on quinoline. The interaction of long-chain amines with 2-chloroquinoline was carried out in the environment of pyridineThe reaction results were obtained condensation products of 1- (2-chloroquinolin-3-yl) -Nalkylmethanimines. A large hydrocarbon chain near iminium nitrogen increases the lyophilicity of azomethines, which may potentially affect the rate of pharmacological action. The condensation reactions of 2-chloroquinoline-3-carbaldehyde were carried out with hexanoic and octanoic acid hydrazides in ethanol, allowing to obtain high yields hydrazones. It should be noted that the reaction produces a mixture of syn- and anti-isomers. To determine the effect of the substituent at position 2 quinoline, condensations of synthetically available 2-thioquinoline-3-carbaldehyde with amines and acid hydrazides were conducted. The interaction between thioquinolinecarbaldehyde and octylamine in an ethyl alcohol environment results in the formation of a condensation product of 3 - [(octylimino) methyl] quinoline-2-thiol. In the case of condensation of 2-thioquinoline-3-carbaldehyde with octanoic acid hydrazide, hydrazone is formed, which is a mixture of syn- and anti-isomers in a ratio of 1: 1.2. It should be noted that the obtained long-chain thio derivatives of quinoline can be used as complexing agents for the determination of metals. The structure of the obtained compounds was proved by the spectra of nuclear magnetic resonance. Keywords: quinolinecarbaldehyde; amines; acid hydrazides; condensation; Schiff's basics.