Quinoline Alkaloids. Part 23. Reactions of 3-Prenyl-2-Quinolones with N-Halosuccinimides. Synthesis of 5-Methoxy-2,2-Dimethyl-2h-Pyrano[2,3-B] Quinoline and N-Methylflindersine

Reaction of atanine (1) with N-bromosuccinimide gave a mixture of a bromofuroquinoline (3) and a bromo-pyranoquinoline (4); the latter was converted into 5-methoxy-2,2-dimethyl-2H-pyrano[2, 3-b]quinoline (5). Reaction of an N-methyl-3-prenyl-quinolone (6) with N-chlorosuccinimide furnished a chloro-...

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Bibliographic Details
Published in:Proceedings of the Royal Irish Academy. Section B. Biological, geological and chemical science geological and chemical science, 1983-01, Vol.83B, p.103-106
Main Authors: Grundon, M. F., Harrison, D. M., Magee, M. G., Rutherford, M. J., Surgenor, S. A.
Format: Article
Language:English
Subjects:
Alkaloids
Ethers
Evaporation
Mass spectroscopy
Pyridines
Quinoline alkaloids
Quinolones
Tetrahedrons
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Summary:Reaction of atanine (1) with N-bromosuccinimide gave a mixture of a bromofuroquinoline (3) and a bromo-pyranoquinoline (4); the latter was converted into 5-methoxy-2,2-dimethyl-2H-pyrano[2, 3-b]quinoline (5). Reaction of an N-methyl-3-prenyl-quinolone (6) with N-chlorosuccinimide furnished a chloro-pyrano-quinolone (7) which was converted into N-methylflindersine (8; R = Me); two other syntheses of the latter alkaloid are described.
ISSN:0035-8983