64388-18-7Relevant academic research and scientific papers
Catalyst-Free Synthesis of 2-Anilinoquinolines and 3-Hydroxyquinolines via Three-Component Reaction of Quinoline N-Oxides, Aryldiazonium Salts, and Acetonitrile
Dhiman, Ankit Kumar,Chandra, Devesh,Kumar, Rakesh,Sharma, Upendra
, p. 6962 - 6969 (2019/06/14)
A rapid microwave-assisted, catalyst-free, three-component synthesis of various 2-anilinoquinolines from quinoline N-oxides and aryldiazonium salts in acetonitrile under microwave irradiation is reported. This reaction utilizes acetonitrile as a single nitrogen source and involves the formation of two new C-N bonds via the formal [3 + 2] cycloaddition reaction. In the case of 2-substituted quinolines, 3-hydroxyquinoline was observed as the main product via a 1,3 shift of the oxygen atom from N-oxide to the C3 position of quinolines.
Combining C-H functionalisation and flow photochemical heterocyclic metamorphosis (FP-HM) for the synthesis of benzo[1,3]oxazepines
Babra, Jasraj S.,Russell, Andrew T.,Smith, Christopher D.,Zhang, Yuxiong
, p. 5351 - 5357 (2018/05/31)
C-H Activation/functionalisation and Flow Photochemical Heterocyclic Metamorphosis (FP-HM) have been combined to synthesize a library of benzo [1,3]oxazepines, a rarely described heterocyclic family. This combined protocol allows a range of arylated products to be made from simple starting materials, and the cheap flow photochemical system has proven effective for rapid synthesis of gram-quantities of benzo [1,3]oxazepines.
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.
Cu(OAc)2-catalyzed direct radical C2 arylation of quinoline N-oxide with arylamines
Yuan, Jin-Wei,Liu, Shuai-Nan,Qu, Ling-Bo
, p. 2267 - 2275 (2017/03/24)
A Cu(OAc)2-catalyzed synthesis of 2-arylquinoline N-oxides with easily available arylamines is described. The main features of this reaction are mild reaction conditions, high functional-group tolerance, excellent regioselectivity, and good to excellent yields. This procedure is mild, operationally simple, and constitutes a greener approach to the arylation of quinoline N-oxides.
