952340-26-0Relevant academic research and scientific papers
4-Aryl-2-quinolones through a Pseudo-Domino Heck/Buchwald-Hartwig reaction in a molten tetrabutylammonium acetate/ tetrabutylammonium bromide mixture
Battistuzzi, Gianfranco,Bernini, Roberta,Cacchi, Sandro,De Salve, Ilse,Fabrizi, Giancarlo
, p. 297 - 302 (2007)
4-Aryl-2-quinolones can be prepared from readily available o-bromocinnamamide and aryl iodides using phosphine-free palladium(II) ace-tate as the precatalyst and a molten tetra(n-butyl)-ammonium acetate/tetra(n-butyl) ammonium bro-mide mixture as the reac
Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides
Maity, Rajib,Naskar, Sandip,Das, Indrajit
, p. 2114 - 2124 (2018/02/23)
Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.
The Heck reaction of β-arylacrylamides: An approach to 4-aryl-2-quinolones
Bernini, Roberta,Cacchi, Sandro,De Salve, Ilse,Fabrizi, Giancarlo
, p. 2947 - 2952 (2008/02/12)
The Heck reaction of β-arylacrylamides with aryl iodides afforded the corresponding vinylic substitution products usually in high yields. The nature of β-substituents, aryl iodides and substituents at the nitrogen atom influences the stereochemical outcome. N,N-Dimethyl-β-arylacrylamides gave vinylic substitution products with higher stereoselectivity than the corresponding N-unsubstituted β-arylacrylamides. β-Arylacrylamides containing ortho-substituents led to the formation of only one stereoisomer. The procedure was used to prepare 4-aryl-2-quinolones from β-(obromophenyl) acrylamide through a sequential Heck reaction and copper-catalyzed cyclization process. Georg Thieme Verlag Stuttgart.
