7- Hydroxyquinoline, allylation

Allylation of the 7-hydroxyquinoline derivative 242 with allyl bromide gave the corresponding 7-allyl ether 243 which underwent Claisen rearrangement to give the 8-allyl derivative 244. Acylation and subsequent bromination afforded the dibromopropyl derivative 245. Treatment of 245 with KOH/EtOH gave 8-hydroxypyrroloquinoline 246 that was methylated with methyl iodide to afford 247 (91JOC980) (Scheme 44). 

Allyl and crotyl ethers were prepared from 3-propyl-4-quinolones by two different approaches. Displacement of 4-chloro-3-propyl-quinoline by the sodium salt of the two alcohols gave the ethers (1) as clean products, whereas reacting 3-propyl-4-hydroxyquinoline with allyl bromide in the presence of sodium ethoxide afforded not only the allyl ether but also the 1-allylquinolone (2). The products were well-characterized by their ultraviolet spectra and infrared bands. Rearrangement of the ethers at 200° without solvent gave quantitative yields of the corresponding l-allyl-3-propyl-4-quinolones (2). 

Hydroxyquinoline sulfate 9441 Isobutyl cyanide 7068 5-Isopropyl-5-allyl-2,4,6(l//,3//,5/f)- ... 

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