Quinoline alkaloids. Part XI. A study of the Claisen rearrangement of the 3, 3-dimethylallyl ether of 4-hydroxy-1-methyl-2-quinolone. Synthesis of ifflaiamine and the …

TR Chamberlain, MF Grundon

文献索引：Chamberlain,T.R.; Grundon,M.F. Journal of the Chemical Society [Section] C: Organic, 1971 , p. 910 - 914

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被引用次数: 10

摘要

Claisen rearrangement of 1-methyl-4-(3-methylbut-2-enyloxy) 2-quinolone resulted mainly in abnormal reaction to give a 1, 2-dimethylallylquinoline and its linear and angular cyclisation products. The intermediate 1, 1-dimethylallylquinoline was trapped as its acetate which was cyclised to ifflaiamine with hydrobromic acid. An isomeric furanoquinoline alkaloid is shown to occur with ifflaiamine in Flindersia ifflaiana and the biogenesis of the ...