128676-88-0Relevant academic research and scientific papers
Synthesis of 2-Quinolinones through Palladium(II) Acetate Catalyzed Cyclization of N -(2-Formylaryl)alkynamides
Zhang, Jianbo,Han, Xiuling,Lu, Xiyan
, p. 1744 - 1748 (2015)
A Pd(OAc)2-catalyzed cyclization of N-(2-formylaryl)alkynamides initiated by the oxypalladation of alkynes was developed. The method provides a new approach for the efficient and atom-economical synthesis of 2-quinolinone derivatives.
Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4
Liu, Xu,Xin, Xin,Xiang, Dexuan,Zhang, Rui,Kumar, Santosh,Zhou, Fenguo,Dong, Dewen
, p. 5643 - 5646 (2012/08/08)
A facile and efficient synthesis of substituted quinolin-2(1H)-ones is developed via intramolecular cyclization of penta-2,4-dienamides mediated by concentrated H2SO4 (98%), and a mechanism involving the formation of a dicationic superelectrophile, and subsequent intramolecular nucleophilic cyclization reactions is proposed.
Directed ortho-Lithiation of Chloroquinolines. Application to Synthesis of 2,3-Disubstituted Quinolines
Marsais, F.,Godard, A.,Queguiner, G.
, p. 1589 - 1594 (2007/10/02)
2-, 3- and 4-Chloroguinolines were selectively lithiated at low temperature by lithium diisopropylamide at the more acidic C-3, C-4 and C-3 positions respectively.Reaction of 2-chloro-3-lithioquinoline with electrophiles led to various 2,3-disubstituted quinolines.The versatility of this functionalization methodology is enhanced by the C-2 halogen reactivity towards oxygen or nitrogen nucleophiles.So, a great variety of 2,3-disubstituted quinolines were synthesized, such as 2-chloro, 2-alkoxy, 2-aminoquinolines or 2-quinolones bearing an hydroxy, carbonyl (aldehyde, ketone or carboxylic acid), iodo, trimethylsilyl or boronic acid moiety at the C-3.Some of the resulting 2,3-disubstituted synthons were annelated to tetracyclic polyaromatics, which possess the xanthone or indole structure.This could be achieved via further functionalization of the quinoline ring either by SNAr2 or heteroaromatic cross-coupling reactions, after the first directed-lithiation step.
