1401421-12-2Relevant academic research and scientific papers
Copper-Catalyzed Aerobic Annulation of Hydrazones: Direct Access to Cinnolines
Lan, Chunling,Tian, Zhuang,Liang, Xuchun,Gao, Mingchun,Liu, Wenting,An, Yu,Fu, Wencheng,Jiao, Guanming,Xiao, Junjie,Xu, Bin
, p. 3735 - 3740 (2017/10/07)
A novel method was developed for the construction of biologically active poly-substituted cinnolines from easily accessible hydrazones in good to excellent yields. A simple copper catalyst could efficiently promote C?N bond formation through selective C?H functionalization and dehydrogenative amination. Furthermore, the inert C?Heteroatom (O/F/N) bonds are susceptible to cleavage in high selectivity in the newly developed aerobic annulation, in preference to the alternative C?H bond, which is left intact. (Figure presented.).
Multicomponent Coupling Cyclization Access to Cinnolines via in Situ Generated Diazene with Arynes, and α-Bromo Ketones
Shu, Wen-Ming,Ma, Jun-Rui,Zheng, Kai-Lu,Wu, An-Xin
supporting information, p. 196 - 199 (2016/02/03)
A transition-metal-free multicomponent coupling cyclization reaction was explored involving arynes, tosylhydrazine, and α-bromo ketones. The reaction proceeds via a formal [2 + 2 + 2] cycloaddition, giving access to cinnoline derivatives in moderate yields under mild conditions. Three chemical bonds were formed-two C-N bonds and one C-C bond-in a single step.
Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines
Zhang, Guangwu,Miao, Jinmin,Zhao, Yan,Ge, Haibo
, p. 8318 - 8321 (2012/09/07)
O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives. Copyright
