7678-83-3Relevant academic research and scientific papers
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.
TMP-magnesium and TMP-Zinc bases for the regioselective metalation of the cinnoline scaffold
Klatt, Thomas,Roman, Daniela Sustac,Leon, Thierry,Knochel, Paul
supporting information, p. 1232 - 1235 (2014/03/21)
A regioselective functionalization of cinnolines in positions 3 and 8 using metalations has been developed. This involves either the use of a frustrated Lewis pair consisting of BF3·Et2O and TMP 2Mg·2LiCl or the in situ generated base TMP 2Zn·2MgCl2·2LiCl. Successive metalations allow the preparation of 3,8-disubstituted cinnolines. Various functionalizations by acylation, allylation, and cross-coupling reactions with aryl halides or alkenyl iodides were carried out successfully.
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
Copper-catalyzed tandem C-N bond formation: An efficient annulative synthesis of functionalized cinnolines
Ball, Catherine J.,Gilmore, Jeremy,Willis, Michael C.
supporting information; experimental part, p. 5718 - 5722 (2012/08/14)
Cinn-tillating synthesis: The combination of a readily available copper catalyst, a simple hydrazide nucleophile, and established difunctionalized building blocks provides a new, flexible route to an under-developed class of aromatic heterocycles, cinnolines (see scheme). Copyright
