A clean procedure for synthesis of phenylquinoline derivatives

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In this investigation the reaction of cyclohexanone 1 with benzaldehyde 2 yielded (E)-2- benzylidenecyclohexanone 3, which on reaction with 3-oxo-N-phenylbutanamide afforded 1-(1, 4, 5, 6, 7, 8-hexahydro-2-hydroxy-1, 4-diphenylquinolin-3-yl) ethanone.4. While the treatment of 4 with ethylbromoacetate and bromophenylethanone afforded the compounds 5 and 6 respectively. However, treatment of 4 with phosphoryltrichloride gave the corresponding compound 7. The reaction of compound 4 with hydrazine hydrate in ethanol led to the formation 4, 5, 6, 7, 8, 9-hexahydro-3-methyl-4,9-diphenyl- 1H-pyrazolo [3, 4-b] quinoline 8. 1, 2, 3, 4, 5, 6, 7, 8-Octahydro-2-oxo-4-phenylquinoline-3-carbonitrile 9 was prepared followed by reacting with ethyl chloroacetate in the presence of anhydrous sodium acetate to produce carbonitrile derivative 10. Compound 10 was reacted with hydrazine hydrate in ethanol to give the corresponding hydrazides 11, which was reacted with D-glucose in acetic acid to afford nucleoside derivative 12. The biological activity of the prepared compounds was also described.

Quinoline; hydrazine hydrate; ethylbromoacetate