Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH
Organic & Biomolecular Chemistry Pub Date: 2005-12-05 DOI: 10.1039/B512729G
Abstract
Six-membered photochemical cyclisations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. The decrease in yield of cyclisation products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the σ-imidazol-2-yl radicals. The seven-membered cyclisation was only successful under photochemical conditions, as radical reduction occurred with tin hydride. Nitration of 5,6-dihydroimidazo[2,1-a]isoquinoline with nitric/sulfuric acid occurred at the 2- and 8-positions.
Recommended Literature
- [1] An aptamer-based keypad lock system? Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang WangChem. Commun., 2012,48, 802-804 10.1039/C1CC15979H
- [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 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
- [4] 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
- [5] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [6] An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction? Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin JinJ. Mater. Chem. C, 2020,8, 192-200 10.1039/C9TC05297F
- [7] 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
- [8] 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
- [9] 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
- [10] 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
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)