6760-40-3Relevant academic research and scientific papers
Utilization of aromatic denitrocyclization reaction for the synthesis of 3-unsubstituted 1,4-dihydroquinolin-4-one derivatives
Radl, Stanislav,Obadalova, Iva
, p. 822 - 832 (2007/10/03)
Synthesis of 3-unsubstituted 1-alkyl- and 1-aryl-1,4-dihydroquinolin-4-ones from 2-nitroacetophenone via the corresponding 3-amino-1-(2-nitrophenyl)prop-2- en-1-ones and -but-2-en-1-ones by denitrocyclization reaction is described. The nucleophilic cyclization was achieved either by sodium hydride or potassium carbonate in DMF.
Reactions of 1-Methyl-4-quinolone with 2-Lithio-1,3-dithianes
Griera, Rosa,Rigat, Lluis,Alvarez, Mercedes,Joule, John A.
, p. 1223 - 1228 (2007/10/02)
Nucleophiles, including lithiated 1,3-dithianes, add to 1-methyl-4-quinolone at the 2-position; in some cases initial adducts were subsequently trapped with added electrophile.
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.
The Oxidation of 1-Alkyl(aryl)quinolinium Chlorides with Rabbit Liver Aldehyde Oxidase
Angelino, S. A. F. G.,Valkengoed, B. H. van,Buurman, D. J.,Plas, H. C. van der,Mueller, F.
, p. 107 - 112 (2007/10/02)
1-Alkyl(aryl)quinolinium chlorides are oxidized by rabbit liver aldehyde oxidase at positions C-2 and C-4.The site and the maximum rate of oxidation are dependent on the size and the steric conformation of the N-1 substituent.The presence of a 3-carboxamido group directs the oxidation completely to position C-4, irrespective of the size of the N-substituent.Application of covalent amination in liquid ammonia as an "enzyme model" for the oxidation of these compounds shows little resemblance.
