Quinolin-2-ones, 4-hydroxy-3-acetyl

The Bischler-Napieralski synthesis of l-methyl-3,4-dihydroisoquinoline (18) from N-(2-phenylethyl)acetamide (19) in the presence of heat and acid (72) was not predicted by the Electrophilic Aromatic module of CAMEO this module of CAMEO predicted instead the formation of methyl 2-acetyl-phenethylamine, 20 (Scheme 5). In a related case, CAMEO predicted (when the Electrophilic Aromatic module was chosen) that 4-anilino-butan-2-one (21) would undergo intramolecular cyclization to form 4-hydroxy-4-methyl-tetrahydroquinoline, 23 (Scheme 6). Apparently, CAMEO correcdy perceives the eneamine character of 21 as necessary for this reaction to occur. It was noted in this case that ring formation, as predicted by CAMEO, depended upon the presence of mineral acid, but did not occur if a Lewis acid (e.g., stannic chloride) was selected instead as the reagent. It is known, however, that intramolecular cyclization of 21 does occur in the presence of a Lewis acid and yields 4-methyl-quinoline, 22, as product (74). 

Anti-HIV activity 1 -Hydroxy-W-methylacridone, 2-(pent-1 -enyl)quinoline, 2-(pent-2-en) quinolin, 2-acetyl-4(3H)-quinazolinone, 2- -pentylquinoline, 3-prenyl-4-prenyloxyquinolin-2-one, 4-methoxy-l-methylquinolin-2-one, )V-methyl-3,3-diprenylquinoline-2,4-dione, buchapine, y-fagarine, haplopine, (-1-)-platydesmine, uranidine [28, 30, 34, 38,40,41],... 

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