22609-00-3Relevant academic research and scientific papers
Redox-Neutral Couplings between Amides and Alkynes via Cobalt(III)-Catalyzed C-H Activation
Kong, Lingheng,Yu, Songjie,Zhou, Xukai,Li, Xingwei
, p. 588 - 591 (2016)
C-H activation assisted by a bifunctional directing group has allowed the construction of heterocycles. This is ideally catalyzed by earth-abundant and eco-friendly transition metals. We report Co(III)-catalyzed redox-neutral coupling between arenes and alkynes using an NH amide as an electrophilic directing group. The redox-neutral C-H activation/coupling afforded quinolines with water as the sole byproduct.
A Tf2O-Promoted Synthesis of Functionalized Quinolines from Ketoximes and Alkynes
Zheng, Weiping,Yang, Weiguang,Luo, Dongping,Min, Lin,Wang, Xinyan,Hu, Yuefei
supporting information, p. 1995 - 1999 (2019/03/13)
A new general synthesis of quinolines was developed from ketoximes and alkynes in the presence of Tf2O. It offered the first direct synthesis of quinolines by using the nitrilium salts generated in situ from a Tf2O-promoted Beckmann rearrangement of ketoximes under very easy conditions. (Figure presented.).
Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine
Li, Lian-Hua,Niu, Zhi-Jie,Liang, Yong-Min
supporting information, p. 15300 - 15304 (2017/10/20)
A concise, novel and flexible metal-free single step to synthesize functionalized quinolines is reported. Triflic anhydride-mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio- and chemoselectivity, and widely tolerable substrates. This approach provides a straightforward and efficient way to construct azaheterocycle structures.
Control over Organometallic Intermediate Enables Cp?Co(III) Catalyzed Switchable Cyclization to Quinolines and Indoles
Lu, Qingquan,Vásquez-Céspedes, Suhelen,Gensch, Tobias,Glorius, Frank
, p. 2352 - 2356 (2016/04/26)
Achieving controllable C-H functionalization to elaborate valuable compounds from simple chemicals is attractive and highly desirable, especially if nonprecious transition metal catalysts can be used. However, controlling selectivity in these transformations remains a continuous challenge to synthetic chemists. Herein, we show for the first time that control over the reactive organometallic intermediate enables the switchable synthesis of quinoline and indole from amides and alkynes through C-H activation using Cp?Co(III). The keys to this strategy are (1) introducing a Lewis acid to greatly accelerate the dehydrative cyclization, which can outcompete dehydrogenative cyclization, and (2) tuning the directing group to facilitate the dehydrogenative cyclization and inhibit dehydrative cyclization.
Green Protocol for the Friedlaender Synthesis: KAL(SO4)2·12H2O-SiO2 (ALUM-SiO2) A Highly Efficient Catalyst in the Synthesis of Quinolines
Mohammadi, Ali A.,Azizian, Javad,Hadadzahmatkesh, Armin,Asghariganjeh, Mohammad R.
, p. 947 - 954 (2008/09/21)
In this letter, an efficient synthesis of an array of poly-substituted quinolines from 2-aminoaryl ketones and β-ketoester, β-diketones and α-methylene ketones using KAl(SO4)2·12H2O-SiO2 (Alum-SiO2) u
