55182-92-8Relevant academic research and scientific papers
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.
Kolbe Synthesis of Unsaturated Pheromones by Coelectrolysis with 5-Alkynoic Acids
Seidel, Wolfgang,Schaefer, Hans J.
, p. 3898 - 3903 (2007/10/02)
The alkynoic acids 5a - g are synthesized by coelectrolysis of 5-alkynoic acids 2a - c with dicarboxylic monoesters 3a - d.By reduction, Lindlar-hydrogenation, and acetylation these are converted into pheromones such as (Z)-11-hexadecenyl acetate (7b), the pheromone of Mamestra brassicae. 2a - c can be prepared by alkynylation of 1-bromo-3-chloropropane to 1a - c, substitution by cyanide and hydrolysis.
