Polyfluoroheterocyclic compounds. Part IX. Tautomerism in polyfluorohydroxy-quinolines and -isoquinolines
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39670000053
Abstract
Heptafluoroquinoline with aqueous sodium hydroxide or with potassium hydroxide in t-butyl alcohol gives a mixture of 2- and 4-hydroxyhexafluoroquinolines; heptafluoroisoquinoline reacts to give the 1-hydroxy-derivative. 2-Hydroxyhexafluoroquinoline and 1-hydroxyhexafluoroisoquinoline exist as tautomers and react with diazomethane giving a mixture of O- and N-methyl derivatives whereas 4-hydroxyhexafluoroquinoline gives only an O-methyl derivative. The factors affecting tautomerism in these systems are outlined.
Recommended Literature
- [1] An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu ChenRSC Adv., 2015,5, 100775-100782 10.1039/C5RA21508K
- [2] An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon? Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu MaRSC Adv., 2021,11, 37631-37642 10.1039/D1RA04788D
- [3] 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
- [4] An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands? Eric Wimmer,Daniel Cortés-Borda,Solène Brochard,Elvina Barré,Charlotte Truchet,Fran?ois-Xavier FelpinReact. Chem. Eng., 2019,4, 1608-1615 10.1039/C9RE00096H
- [5] An atomic scale study of defects in Co2FeAl Ravi Kumar Yadav,R. GovindarajPhys. Chem. Chem. Phys., 2020,22, 26876-26886 10.1039/D0CP04572A
- [6] An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. KillardAnalyst, 2008,133, 391-399 10.1039/B716154A
- [7] An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction? Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui SongNanoscale, 2020,12, 7024-7034 10.1039/D0NR00001A
- [8] An antioxidant self-healing hydrogel for 3D cell cultures? Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei TaoJ. Mater. Chem. B, 2020,8, 1383-1388 10.1039/C9TB02792K
- [9] An integrated cathode and solid electrolyte via in situ polymerization with significantly reduced interface resistance? Jialiang Yuan,Ran Dong,Yuan Li,Yang Liu,Zhuo Zheng,Yuxia Liu,Yan Sun,Benhe Zhong,Zhenguo Wu,Xiaodong GuoChem. Commun., 2021,57, 13004-13007 10.1039/D1CC04485K
- [10] An analysis of the WTC fires using CIB correlations and simple modeling JGQuintiere 10.1177/0734904121989670
Journal Name：Journal of the Chemical Society C: Organic
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)