98815-39-5Relevant articles and documents
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
supporting information, (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.
Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib
Wan, Chao,Pang, Jian-Yu,Jiang, Wei,Zhang, Xiao-Wei,Hu, Xiang-Guo
, p. 4557 - 4566 (2021/03/01)
We have identified a new reactivity of copper/diamine catalysis for the reductive ring-cleavage of isoxazoles to yield fluoroalkylated enaminones. This protocol has the advantage of using commercially available reagents, ease of setting up, broad tolerance of functionality, and is regiospecific and free of defluorination and reduction of reducible functional groups. The utility was demonstrated by a one-step, regioselective synthesis of fluoroalkylated pyrazole-based drugs such as celecoxib, deracoxib, and mavacoxib.
Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides
Liu, Rui-Hua,Shen, Zhen-Yao,Wang, Cong,Loh, Teck-Peng,Hu, Xu-Hong
supporting information, p. 944 - 949 (2020/02/15)
We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.