Kunavina E.A., Dyusenov A.I., Zhdanova A.V., Kozminykh V.O.
HETEROCYCLIZATION OF THE ALKYL(ARYL)METHYLKETONES, DIETHYLOXALATE AND META-REPLACED AROMATIC AMINES IN THE SYNTHESIS OF QUINOLINE-2-CARBOXYLIC ACID
Rather large number of various medicinal preparations at which molecules there are heterocyclic systems of quinolone is known. Derivatives of a quinoline-2-carboxylic acid are potential biologically active materials, which have various biological activity. So, Atophanum (phenoquin) is received from acetophenone and an isatin by the Frindler method is applied as against arthritis means. Primachinum and plasmochin are the anti-malarial drug operating on gametes of a plasmodium of a malaria. Also some derivatives are applied as anesthetics or as drug against oncological diseases and as antibacterial medicament. Equimolar condensation of a ketone and dimethyl ester of oxalic acid received the intermediate diketoester. At addition to it the bases 7-hydroxy- and 7-amino-4-methylquinolines-2-carboxylic acids, 4-(4’-bromphenil)-7-hydroxy- and 7-amino-4-(4’-bromphenil)quinolines-2-carboxylic acids were received. In this article features of reaction depending on the nature of mother substances (alkyl- or arylmethylketones) and nucleophilic reagents (the meta-replaced arylamines), physical and chemical properties of the received connections are discussed. The structure of connections confirmed with data IR-spectroscopies, spectroscopies of nuclear magnetic resonance 1H and mass spectrometries. Proceeding from similarity of structures of the known biologically active materials of a quinolinic row and again synthesized representatives it is assumed that new substances will have potential biological activity and will find application in medical practice as medical drugs.
Key words: heterocyclization, methylketones, dimethyl ester of oxalic acid, meta-aminophenol, meta-phenylene diamine, the 4,7-direplaced quinolines-2-carboxylic acids.
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Authors: Kunavina E.A., Dyusenov A.I., Zhdanova A.V., Kozminykh V.O.