Simple Quinolines and Quinolones of 8-hydroxyquinoline Copper


A series of simple, new 8-hydroxyquinoline Copper alkal […]

A series of simple, new 8-hydroxyquinoline Copper alkaloids were isolated from the timber, an endemic plant of the family Moraceae. Fractionation led to the isolation of the major alkaloidal constituent, 8-hydroxyquinoline-4-carbaldehyde C10H7NO2, mp 155–156°C, in a 0.25% yield from the dried timber. The structure of 1 was established with the aid of spectroscopic data and chemical derivatization. Changes observed in the NMR spectrum of 1 in methanol-d4 were attributed to the in situ formation of its hemiketal 3.

Two minor alkaloids were also isolated. The structure of one of these, C10N8N2O2, mp 223–224°C, was revised from 3,4-dihydroxy-2,2′-bipyridine to 8-hydroxyquinoline-4-carbaldehyde oxime based on synthetic, 1H NMR and nuclear overhauser effect (NOE) difference NMR spectroscopic evidence. Natural occurrence of oximes, although rare in higher plants, is not without precedence, and the essential oil of Ruta Montana L. has been reported to contain the bis-oxime of 3,4-hexanedione. The structure of the nonpolar minor alkaloid broussonetine, C22H16N2O4, mp 238-239°C, was elucidated as 3,4-bis(8-hydroxyquinoline-4-yl)-γ-butyrolactone.

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