Synthesis of fused tricyclic indolizines by intramolecular silver-mediated double cyclization of 2-(pyridin-2-yl)acetic acid propargyl esters?
RSC Advances Pub Date: 2017-05-03 DOI: 10.1039/C7RA00892A
Abstract
The treatment of a toluene solution of easily accessible 2-(pyridin-2-yl)acetic acid propargyl esters with 2.0 equiv. of Ag2CO3 in the presence of potassium acetate (2.0 equiv.) at 100 °C afforded fused tricyclic indolizines in good to excellent yields. The reaction proceeded through a domino silver-mediated double cyclization sequence involving a 5-exo-dig cyclization and 1,3-hydrogen shift followed by an intramolecular cycloisomerization.
Recommended Literature
- [1] Embedding heteroatoms: an effective approach to create porphyrin-based functional materials Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro OsukaDalton Trans., 2017,46, 13322-13341 10.1039/C7DT02815F
- [2] Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe? Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. MarqueChem. Sci., 2021,12, 4154-4161 10.1039/D0SC06470J
- [3] EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis? Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” KimLab Chip, 2009,9, 1732-1739 10.1039/B821508A
- [4] 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
- [5] Emulsion technologies for multicellular tumour spheroid radiation assays? Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele ZagnoniAnalyst, 2016,141, 100-110 10.1039/C5AN01382H
- [6] Dissociation of large gaseous serine clusters produces abundant protonated serine octamer Jacob S. Jordan,Evan R. WilliamsAnalyst, 2021,146, 2617-2625 10.1039/D1AN00273B
- [7] Excitation energies from ground-state density-functionals by means of generator coordinates A. B. F. da Silva,K. CapellePhys. Chem. Chem. Phys., 2009,11, 4564-4569 10.1039/B902529D
- [8] Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells? Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re AlsbergJ. Mater. Chem. A, 2015,3, 9851-9860 10.1039/C5TA00625B
- [9] Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals? Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael HardyAnalyst, 2019,144, 4194-4203 10.1039/C9AN00468H
- [10] Excellent lithium ion storage property of porous MnCo2O4 nanorods? Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen FangRSC Adv., 2016,6, 23074-23084 10.1039/C5RA26176G
Journal Name：RSC Advances
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)