Regiochemistry of nucleophilic substitution of pentachloropyridine with N and O bidentate nucleophiles?
New Journal of Chemistry Pub Date: 2015-03-18 DOI: 10.1039/C5NJ00418G
Abstract
Site reactivity of some enol–imines derived from N-aryl formamides with pentachloropyridine under basic conditions in dry CH3CN was investigated. The aromatic nucleophilic substitution of pentachloropyridine with enol–imines occurs at the 4-position of pyridine ring by both oxygen and nitrogen site of enol–imines. Nucleophilic attack by the oxygen of enol–imine gave corresponding oximino compounds as a mixture of E- and Z-isomers. In contrast, nucleophilic attack by the nitrogen of enol–imine gave the unexpected N,N-di-substituted aryl compounds. The structures of all the compounds were confirmed by IR, 1H NMR, 13C NMR and 19F NMR spectroscopy as well as elemental analysis and X-ray crystallography.
Recommended Literature
- [1] 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
- [2] An Assessment of the Laminar Hypersonic Double-Cone Experiments in the LENS-XX Tunnel JaideepRay,PatrickBlonigan,EricT.Phipps,KathrynMaupin 10.2514/1.j062802
- [3] An aptamer-based keypad lock system? Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang WangChem. Commun., 2012,48, 802-804 10.1039/C1CC15979H
- [4] An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai KongAnalyst, 2017,142, 3579-3587 10.1039/C7AN01026E
- [5] An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting? Lab Chip, 2019,19, 524-535 10.1039/C8LC01170B
- [6] An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods? M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. OrtizJ. Mater. Chem. C, 2018,6, 12643-12651 10.1039/C8TC03187H
- [7] An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes? H. V. Jain,D. Verthelyi,S. L. BeaucageRSC Adv., 2017,7, 42519-42528 10.1039/C7RA04247G
- [8] An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems RabailGul,MariamMir,MurtazaNAli 10.1177/08853282231160212
- [9] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [10] An atomistic mechanism for the degradation of perovskite solar cells by trapped charge? Eunhak Lim,Jiyoung Heo,Seong Keun KimNanoscale, 2019,11, 11369-11378 10.1039/C9NR02193K
Journal Name：New Journal of 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)