Synthesis and antibacterial activities of some substituted 2-styrylquinolines | Abstract

Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

ISSN: 0975-413X
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Synthesis and antibacterial activities of some substituted 2-styrylquinolines

Author(s): G. Anukumari*, M Anand Rao and PK Dubey

p-Anisidine (1) on treatment with ethyl acetoacetate in refluxing ethanol for 4 hrs gave ethyl 3-[(4- methoxyphenyl)imino]butanoate (2) which on thermal cyclisation in hot Dowtherm oil at 250 oC gave 4-hydroxy-6- methoxy-2-methylquinoline (3). The latter on heating with dimethyl sulphate in refluxing toluene followed by alkali treatment of the methosulphate salt gave 4,6-dimethoxy-2-methylquinoline (4) which on condensation with aromatic aldehydes (5a-e) gave the corresponding styryl compounds, 4,6-dimethoxy-2-styrylquinolines (6a-e). 3 on further treatment with dialkyl sulphates and aryl methyl halides in refluxing acetone containing K2CO3 gave N-alkyl and Narylmethyl- 6-methoxy-2-methylquinoline (7a-c). The products thus obtained have been characterised from their spectral data and have been evaluated for their antibacterial activities. Furthermore, 4 & 7 represent products obtained by chemoselective alkylation of 3 under different conditions.


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