3475-16-9Relevant academic research and scientific papers
Visible-light-promoted c2 selective arylation of quinoline and pyridine n-oxides with diaryliodonium tetrafluoroborate
Li, Dazhi,Liang, Ce,Jiang, Zaixing,Zhang, Junzheng,Zhuo, Wang-Tao,Zou, Fan-Yue,Wang, Wan-Peng,Gao, Guo-Lin,Song, Jinzhu
, p. 2733 - 2742 (2020/03/11)
A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This met
Rh(III)-Catalyzed C(8)-H Functionalization of Quinolines via Simultaneous C-C and C-O Bond Formation: Direct Synthesis of Quinoline Derivatives with Antiplasmodial Potential
Sharma, Ritika,Kumar, Rakesh,Kumar, Rohit,Upadhyay, Pooja,Sahal, Dinkar,Sharma, Upendra
supporting information, p. 12702 - 12710 (2018/10/15)
Here, a facile and efficient protocol for the synthesis of 3-hydroxyquinolin-8-yl propanoates via Rh(III)-catalyzed C(8)-H activation of 2-substituted quinolines has been developed. The reaction proceeds via C(8)-H activation, functionalization with acrylates, followed by intramolecular migration of the oxygen atom from quinoline N-oxides to the acrylate moiety. In this approach, N-oxide plays a dual role of a traceless directing group as well as a source of an oxygen atom for hydroxylation. This catalytic method involves simultaneous formation of new C-C and C-O bonds and is applicable only for C2-substituted quinolines. A catalytically competent five-membered rhodacycle has been characterized, thus revealing a key intermediate in the catalytic cycle. In silico docking studies against Falcipan-2 have revealed that 3a, 3b, 3g, and 3m have better scores. In vitro evaluation of selected compounds against CQ-sensitive pf3D7 and CQ-resistant pfINDO strains provided evidence that 3d (IC50 13.3 μM) and 3g (IC50 9.5 μM) had good promise against Plasmodium falciparum in the in vitro culture. Compound 3g was found to be the most potent on the basis of both in vitro antiplasmodial activity [IC50 9.5 μM (Pf3D7) and 11.9 μM (PfINDO), resistance index 1.25] and in silico studies.
KMnO4-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids
Yuan, Jin-Wei,Qu, Ling-Bo
supporting information, p. 981 - 985 (2017/05/22)
Direct C[sbnd]H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnO4 as the sole and efficient oxidative system. This method provides an efficient protocol to construct regioselectively 2-arylquinoline N-oxides
Reaction of quinoline N-oxides with alkyl- and aryllithiums in the presence of oxidant
Tagawa, Yoshinobu,Nomura, Manami,Yamashita, Hiroyuki,Goto, Yoshinobu,Hamana, Masatomo
, p. 2385 - 2397 (2007/10/03)
Quinoline and some 4-substituted quinoline 1-oxides react with alkyl- and aryllithiums in the presence of an oxidant to afford 2-alkyl- and 2- arylquinoline 1-oxides in generally good yields. Among oxidants used, 9- fluorenone is most effective. On the other hand, quinaldine 1-oxide undergoes a base-induced electrophilic reaction with n-BuLi and 9-fluorenone to give 2- [(9-hydroxyfluoren-9-yl)methyl]quinoline 1-oxide.
