13720-89-3Relevant academic research and scientific papers
Synthesis of 4-quinolones through nickel-catalyzed intramolecular amination on the β-carbon of o-(N-alkylamino)propiophenones
Ueno, Satoshi,Shimizu, Ryosuke,Maeda, Ryohei,Kuwano, Ryoichi
, p. 1639 - 1642 (2012/07/17)
o-(N-Alkylamino)propiophenones are converted into 4-quinolones in the presence of chlorobenzene, potassium phosphate, morpholine, and nickel(0) catalyst. The reaction proceeds through the nickel-catalyzed formation of β-enaminones from o-(N-alkylamino)propiophenones and morpholine, followed by the intramolecular transamination. Georg Thieme Verlag Stuttgart · New York.
Alkylation of Quinolines with Trialkyl Phosphates. Part 2. Mechanistic Studies
Frank, Judit,Meszaros, Zoltan,Koemives, Tamas,Marton, Attila S.,Dutka, Ferenc
, p. 401 - 406 (2007/10/02)
The mechanism of alkylation of 4-quinolone (3) by trialkyl phosphates has been studied by preparative, kinetic, and isotopic methods, as well as by u.v. spectrophotometry.In a kinetically controlled process the transient initial formation of 4-methoxyquinoline (4a) was established; this was subsequently transformed by trimethyl phosphate to a quaternary N-methyl-4-methoxyquinolinium salt (6a).The latter catalyses the transformation of (4a) by intermolecular ON methyl transfer to the more stable N-methyl-4-quinolone (5a).The end product is a mixture of (5a) and (6a).Their ratio is shifted at higher temperature in favour of (6a).This is due partly to differences in the temperature dependence of the individual reactions and partly to alkylation of (5a) by trimethyl phosphate at higher temperature.A mechanism for the alkylation reaction is proposed.
