Synthesis of 3-acylquinolines through Cu-catalyzed double C(sp3)–H bond functionalization of saturated ketones?
Organic Chemistry Frontiers Pub Date: 2017-02-06 DOI: 10.1039/C6QO00817H
Abstract
A novel synthesis of 3-acylquinolines from Cu-catalyzed one-pot reactions of 2-aminoaryl aldehydes/ketones with inactivated ketones is presented. Mechanistically, the formation of the title compounds involves a cascade procedure including C(sp3)–H bond amination, enaminone formation, and enamine-carbonyl condensation. To our knowledge, this should be the first example in which 3-acylquinolines are prepared through Cu-catalyzed double C(sp3)–H bond functionalization of saturated ketones.
Recommended Literature
- [1] Evolution of hierarchical porous structures in supramolecular guest–host hydrogels? Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. BurdickSoft Matter, 2016,12, 7839-7847 10.1039/C6SM01395C
- [2] Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor? Xinhuan Wang,Shuangfei Cai,Cui QiAnalyst, 2017,142, 2500-2506 10.1039/C7AN00589J
- [3] Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines? Thi Thu Tram Nguyen,Thanh Binh NguyenOrg. Biomol. Chem., 2021,19, 6015-6020 10.1039/D1OB00976A
- [4] Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon? Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng PuChem. Commun., 2019,55, 3963-3966 10.1039/C9CC01213C
- [5] Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent? Yukiya KitayamaPolym. Chem., 2014,5, 2784-2792 10.1039/C3PY01539D
- [6] Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study? Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander OrlovCatal. Sci. Technol., 2015,5, 2059-2064 10.1039/C4CY01563K
- [7] Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita 10.1002/rcm.9494
- [8] Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications Partha Laskar,Christine DufèsNanoscale Adv., 2021,3, 6007-6026 10.1039/D1NA00536G
- [9] Examination of deposit in commercial diluted phosphoric acid Analyst, 1880,5, 146-147 10.1039/AN8800500146
- [10] Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions? Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng CaiChem. Commun., 2013,49, 11086-11088 10.1039/C3CC46560H
Journal Name：Organic Chemistry Frontiers
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)