55182-92-8Relevant articles and documents
The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 17. Synthesis of 2-Alkyl-4-quinolone Alkaloids via a One-step Reaction of N-Methylisatoic Anhydride with Methyl Ketone Enolates
Coppola, Gary M.
, p. 491 - 494 (2007/10/02)
Lithium enolates derived from aliphatic methyl ketones react with N-methylisatoic anhydride (5) at -78 deg C to give 2-alkyl-4-quinolone alkaloids 7 in a single step.The method was used to synthesize both double bond isomers of 1-methyl-2-(8-tridecenyl)-4(1H)-quinolinone (8) thereby showing that the alkaloid evocarpine possesses the Z-olefin stereochemistry 8a.Reduction of 8a provided the alkaloid dihydroevocarpine (16).Compound 16 was also directly prepared from the reaction of 5 with the lithium enolate of 2-pentadecanone.