Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted N-(2-alkynylphenyl)acetamides?
Organic & Biomolecular Chemistry Pub Date: 2018-09-18 DOI: 10.1039/C8OB01870G
Abstract
An efficient method for the synthesis of 3-halogeno-substituted 4-benzoylquinolin-2-(1H)-ones from N-(2-alkynylphenyl)-substituted trihaloacetamides has been developed, in which organic amines (TNPA and DIEA) act as the electron donors. In this carbocyclization reaction, a new C–C bond formation occurred regioselectively via a 6-exo-dig radical cyclization. A variety of useful functional groups are compatible with the reaction conditions. In this process, readily removable organic amines were employed and no heavy metal catalysts were required.
Recommended Literature
- [1] An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells? Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang ChengFood Funct., 2020,11, 10635-10644 10.1039/D0FO02131H
- [2] An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins? Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois MatheyDalton Trans., 2019,48, 5523-5526 10.1039/C9DT00838A
- [3] An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage? Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin ShihRSC Adv., 2015,5, 100783-100789 10.1039/C5RA22482A
- [4] Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode Analyst, 1996,121, 1123-1126 10.1039/AN9962101123
- [5] An integrated system for field analysis of Cd(ii) and Pb(ii) via preconcentration using nano-TiO2/cellulose paper composite and subsequent detection with a portable X-ray fluorescence spectrometer? Xiaofeng LinRSC Adv., 2016,6, 9002-9006 10.1039/C5RA25693C
- [6] An atlas of endohedral Sc2S cluster fullerenes? Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. FowlerPhys. Chem. Chem. Phys., 2017,19, 419-425 10.1039/C6CP07370K
- [7] Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties Huabin Zhang,Shaowu DuCrystEngComm, 2014,16, 4059-4068 10.1039/C3CE42419G
- [8] An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels? Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua SunChem. Commun., 2016,52, 3548-3551 10.1039/C5CC07942J
- [9] An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li YuLab Chip, 2012,12, 317-324 10.1039/C1LC20845D
- [10] An astrophysically-relevant mechanism for amino acid enantiomer enrichment Stephen P. Fletcher,Richard B. C. Jagt,Ben L. FeringaChem. Commun., 2007, 2578-2580 10.1039/B702882B
Journal Name：Organic & Biomolecular Chemistry
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)