Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C–H bond amination mediated by cupric acetate?
Organic & Biomolecular Chemistry Pub Date: 2017-07-24 DOI: 10.1039/C7OB01353A
Abstract
2-(Pyridin-2-yl) aniline was designed as a new, removable directing group in promoting C–H amination mediated by cupric acetate. Employing this auxiliary, the β-C(sp2)–H bonds of benzamide derivatives can be effectively aminated with a variety of amines in moderate to good yields with good functional group tolerance in air. In addition, the quinazolinone derivatives were isolated from the reaction mixture of N-(2-(pyridin-2-yl)phenyl)benzamide with formamide or 5-nitroindole. The corresponding mechanism is discussed. These results indicate that 2-(pyridine-2-yl)aniline can serve as a directing group.
Recommended Literature
- [1] Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR? Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing XiaNanoscale, 2020,12, 20456-20466 10.1039/D0NR04995F
- [2] Distribution pattern and allocation of defects in hydrogenated ZnO thin films? Vitaly Gurylev,Chung-Yi Su,Tsong-Pyng PerngPhys. Chem. Chem. Phys., 2016,18, 16033-16038 10.1039/C6CP01768A
- [3] Evolution and characterization of a benzylguanine-binding RNA aptamer? J. Xu,T. J. Carrocci,A. A. HoskinsChem. Commun., 2016,52, 549-552 10.1039/C5CC07605F
- [4] Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration? Ziyang Deng,Changwei Chen,Sunliang CuiRSC Adv., 2016,6, 93753-93755 10.1039/C6RA20007A
- [5] Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat VeisiNew J. Chem., 2018,42, 1757-1761 10.1039/C7NJ02513K
- [6] Enantiocontrolled construction of sistodiolynne, an unusual polyketide from the wood-decay fungus Sistrema raduloides Chem. Commun., 1997, 767-768 10.1039/A700186J
- [7] 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
- [8] Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets? Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben DaenekeNanoscale, 2016,8, 16276-16283 10.1039/C6NR04326G
- [9] Distinguishing between polymorphic forms of linezolid by solid-phase electronic and vibrational circular dichroism? Jadwiga Frelek,Marcin Górecki,Marta ?aszcz,Agata Suszczyńska,Elemér Vass,Wojciech J. SzczepekChem. Commun., 2012,48, 5295-5297 10.1039/C2CC31207G
- [10] Fe3O4–Pd Janus nanoparticles with amplified dual-mode hyperthermia and enhanced ROS generation for breast cancer treatment? Yanyun Wang,Huijun Ma,Galong Li,Fei Gao,Mingli Peng,Hai Ming FanNanoscale Horiz., 2019,4, 1450-1459 10.1039/C9NH00233B
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.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)