443638-87-7Relevant academic research and scientific papers
Transition Metal-Free Regioselective Remote C?H Bond 2,2,2-Trifluoroethoxylation of 8-Aminoquinoline Derivatives at the C5 Position
Ruyet, Louise,Poisson, Thomas,Besset, Tatiana
supporting information, p. 3407 - 3410 (2021/06/28)
The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61 % yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.
Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides
Chen, Xi,Ding, Ya-Nan,Gou, Xue-Ya,Liang, Yong-Min,Luan, Yu-Yong,Niu, Zhi-Jie,Shi, Wei-Yu,Zhang, Zhe,Zheng, Nian
, p. 8945 - 8948 (2021/09/10)
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C?H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids
Liu, Sien,He, Bangyue,Li, Hongyi,Zhang, Xiaofeng,Shang, Yaping,Su, Weiping
, p. 15628 - 15633 (2021/10/05)
The Rh-catalyzed ortho-C(sp2)?H functionalization of 8-aminoquinoline-derived benzamides with aliphatic acyl fluorides generated in situ from the corresponding acids has been developed. This reaction initiated with 8-aminoquinoline-directed ortho-C(sp2)?H acylation, which was accompanied by subsequent intramolecular nucleophilic acyl substitution of amide group to produce alkylidene phthalides This approach exhibits high stereo-selectivity for Z-isomer products, and tolerates a variety of functional groups as well as aliphatic carboxylic acids with diverse structural scaffolds.
C-H Amidation and Amination of Arenes and Heteroarenes with Amide and Amine using Cu-MnO as a Reusable Catalyst under Mild Conditions
Singh, Harshvardhan,Sen, Chiranjit,Suresh, Eringathodi,Panda, Asit B.,Ghosh, Subhash C.
, p. 3261 - 3275 (2021/02/16)
An atom-economical and efficient route for the direct amidation and amination of aryl C-H bonds using our synthesized recyclable heterogeneous Cu-MnO catalyst is reported here. The direct C-H amidation was carried out using a simple amide without any prea
C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai
supporting information, p. 1352 - 1357 (2021/02/26)
An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale
Ni-Catalyzed C(sp2)-H alkylation ofN-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources
Kano, Taichi,Maruoka, Keiji,Matsumoto, Akira,Sakurai, Shunya,Tsuzuki, Saori
supporting information, p. 7942 - 7945 (2021/08/17)
A Ni-catalyzed direct C-H alkylation ofN-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors is described. The reaction forms a new C(sp3)-C(sp2) bondviathe selective cleavage of both C(sp3)-C(sp3) and C(sp2)-H bonds. This transformation shows a high functional-group tolerance and, due to the structural diversity of alkylsilyl peroxides, a wide range of alkyl chains including functional groups and complex structures can be introduced at theortho-position of readily availableN-quinolylbenzamide derivatives. Mechanistic studies suggest that the reaction involves a radical mechanism.
Copper/Silver Cocatalyzed Regioselective C5-H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds
Zhan, Fuxu,Zhang, Wei,Zhao, Huaiqing
supporting information, p. 1007 - 1014 (2020/04/01)
A copper/silver co-catalyzed cross-dehydrogenative coupling reaction is developed to achieve exclusively remote C5-H coupling of 8-aminoquinoline amides with the methylenic sp 3 C-H bond of 1,3-dicarbonyl compounds. This protocol provides a hig
Copper-Catalyzed Electrochemical Selective Bromination of 8-Aminoquinoline Amide Using NH4Br as the Brominating Reagent
Fang, Ping,Huang, Yan,Mei, Tian-Sheng,Wang, Xiang-Yang,Xu, Hao-Han,Yang, Qi-Liang,Yang, Xiang
, p. 3497 - 3507 (2020/03/23)
A simple and mild protocol for copper-catalyzed bromination of quinoline at the C5 site of quinoline by anodic oxidation was developed, affording the desired remote C-H activation products with isolated yields of up to about 90%. The reaction proceeds wit
Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile
Wen, Chunxia,Zhong, Ronglin,Qin, Zengxin,Zhao, Mengfei,Li, Jizhen
supporting information, p. 9529 - 9532 (2020/09/03)
The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the pr
Metal-Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions Using N-Halosuccinimides
Hou, Jiahao,Wang, Kai,Zhang, Changjun,Wei, Tingting,Bai, Renren,Xie, Yuanyuan
supporting information, p. 6382 - 6386 (2020/10/19)
An efficient and convenient method for electrochemically oxidative dichlorination or dibromination of 8-aminoquinolines on C5 and C7 positions using N-halosuccinimides (NCS and NBS) as the halogen source was described. Substrates with various functional g
