1072913-49-5Relevant academic research and scientific papers
Metal-Free Cascade Annulation Approach for Modular Assembly of Alkynyl/Benzoyl Functionalized Quinolines
Tang, Qiang,Yuan, Meng,Duan, Jiahui,Xu, Keke,Li, Ruxue,Xie, Mengqing,Kong, Shuwen,He, Xinwei,Shang, Yongjia
, (2022/01/19)
A concise and efficient synthetic method for alkynyl quinolines through TfOH-promoted cascade 1,4-conjugate addition/intramolecular annulation/aromatization process is established. By virtue of reactive aza-o-AQM (in situ generated from modular propargylamine), this reaction proceeds smoothly to afford a variety of alkynyl quinolines in good to excellent yields. This transition-metal-free process features halogen groups tolerance, such as the ?Cl, ?Br, and ?I groups; thus, this protocol circumvents the inherent shortcomings of the existing Sonogashira coupling of halogenated quinolines.
Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization
Fan, Jinmin,Wan, Changfeng,Sun, Gaojun,Wang, Zhiyong
supporting information; experimental part, p. 8608 - 8611 (2009/04/04)
(Chemical Equation Presented) Reactions of 2-amino-aryl alcohols with β-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation- cyclization, 2-nitrophenyl propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3- quinolinecarboxylic esters. The mechanistic details of this benzylation/ propargylation and cyclization cascade process are also discussed.
