First synthesis of unexpected functionalized trifluoromethylated 8-oxa-2,4-diazaspiro[5.5]undecanes via one-pot MCRs?
RSC Advances Pub Date: 2014-06-11 DOI: 10.1039/C4RA03199G
Abstract
Ethyl-7,11-diaryl-9-hydroxy-1,3,5-trioxo-9-(trifluoromethyl)-8-oxa-2,4-diazaspiro[5.5]undecane-10-carboxylate derivatives (4) were synthesized from barbituric acid, aromatic aldehydes and ethyl 4,4,4-trifluoro-3-oxobutanoate via a one-pot, multi-component reaction catalyzed by Et3N. The effect of catalyst and temperature on reaction efficiency and yield was investigated. In addition, the treatment of 4 with SOCl2/pyridine in the solvent CH3CN afforded the corresponding dehydrated products 5. A plausible reaction mechanism for the formation of compounds 4 was presented.
![Graphical abstract: First synthesis of unexpected functionalized trifluoromethylated 8-oxa-2,4-diazaspiro[5.5]undecanes via one-pot MCRs](http://scimg.chem960.com/usr/1/C4RA03199G.jpg)
Recommended Literature
- [1] Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. BudaPhys. Chem. Chem. Phys., 2011,13, 10270-10279 10.1039/C1CP20213H
- [2] 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
- [3] An atlas of endohedral Sc2S cluster fullerenes? Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. FowlerPhys. Chem. Chem. Phys., 2017,19, 419-425 10.1039/C6CP07370K
- [4] An aptasensor for the detection of ampicillin in milk using a personal glucose meter Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu ZhangAnal. Methods, 2020,12, 3376-3381 10.1039/D0AY00256A
- [5] Alternative donor substrates for inverting and retaining glycosyltransferases? Luke L. Lairson,Warren W. WakarchukChem. Commun., 2007, 365-367 10.1039/B614636H
- [6] Acenaphthenic hopanoids, a novel series of aromatised Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre AlbrechtChem. Commun., 2001, 1976-1977 10.1039/B105198A
- [7] An all-solid-state asymmetric device based on a polyaniline hydrogel for a high energy flexible supercapacitor? Hamid Heydari,Mohammad B. GholivandNew J. Chem., 2017,41, 237-244 10.1039/C6NJ02266A
- [8] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes? Bo Cao,Yin WeiChem. Commun., 2018,54, 2870-2873 10.1039/C8CC00180D
- [9] An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting? Lab Chip, 2019,19, 524-535 10.1039/C8LC01170B
- [10] An investigation into the origin of variations in photovoltaic performance using D–D–π–A and D–A–π–A triphenylimidazole dyes with a copper electrolyte? Govind ReddyMol. Syst. Des. Eng., 2021,6, 779-789 10.1039/D1ME00073J
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)