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Two alkaloids, 1-methyl-4-(3-methylbut-2-enyloxy)-2-quinolone (revenine : IIc) and 4-methoxy-1-methyl-2-quinolone (IIa), were synthesized by means of a photochemical rearrangement reaction of the corresponding 4-alkoxy-2-methylquinoline 1-oxide (Ic and Ia), which were conveniently prepared from 4-chloro-2-methylquinoline 1-oxide (XVII), which in turn is readily obtainable from 2-methylquinoline 1-oxide via the 4-nitrated compound (XVIII). The mechanism of the photo-rearrangement reaction of 4-alkoxy-2-methylquinoline 1-oxides (Ia-d) in methanol is discussed

A novel synthesis of revenine and related alkaloids by means of a photo-rearrangement reaction of 4-alkoxy-2-methylquinoline 1-oxides.