25666-51-7Relevant academic research and scientific papers
Enantioselective (3+2) cycloaddition: Via N-heterocyclic carbene-catalyzed addition of homoenolates to cyclic N -sulfonyl trifluoromethylated ketimines: Synthesis of fused N-heterocycle γ-lactams
Zhang, Zhen-Zhen,Zhang, Yongna,Duan, Hui-Xin,Deng, Zhuo-Fei,Wang, You-Qing
supporting information, p. 1553 - 1556 (2020/02/13)
An enantioselective (3+2) cycloaddition of enals and cyclic N-sulfonyl trifluoromethyl ketimines via N-heterocyclic carbene-catalyzed homoenolate addition is described. This reaction can efficiently construct fused N-heterocycle γ-lactams bearing two adjacent chiral centers with >20?:?1 dr and 94-99% ee, with one chiral center as a trifluoromethylated α-tetrasubstituted carbon stereocenter.
Halogenation of fluorinated cyclic 1,3-dicarbonyl compounds: new aspects of synthetic application
Sevenard, Dmitri V.,Vorobyev, Mikhail,Sosnovskikh, Vyacheslav Ya.,Wessel, Helma,Kazakova, Olesya,Vogel, Vera,Shevchenko, Nikolay E.,Nenajdenko, Valentine G.,Lork, Enno,R?schenthaler, Gerd-Volker
experimental part, p. 7538 - 7552 (2009/12/06)
In order to elaborate on an approach towards 2-(fluoroacyl)phenols being the superior alternative to the conventional Fries-rearrangement based methodology, the behaviour of cyclic fluorinated 1,3-dicarbonyls in reactions with halogenating agents was examined. The synthetic relevance of the polyhalogenated compounds obtained was demonstrated by the synthesis of several new heterocycles. An aromatization via a halogenation-dehydrohalogenation sequence proved to be a rewarding synthetic route to 2-(fluoroacyl)phenols and previously unknown 3-(fluoroacyl)thiochromones. The structure of one of the synthesized compounds was confirmed by X-ray diffraction analysis.
Oxaziridine-mediated catalytic hydroxylation of unactivated 3° C-H bonds using hydrogen peroxide
Brodsky, Benjamin H.,Du Bois
, p. 15391 - 15393 (2007/10/03)
The design, structural characterization, and evaluation of a unique class of 1,2,3-benzoxathiazine-based oxaziridines as potent O-atom transfer agents for catalytic C-H hydroxylation and alkene epoxidation are described. Turnover of this reaction is made possible by employing a diaryl diselenide cocatalyst and urea·H2O2 as the terminal oxidant. Oxidation of saturated hydrocarbons is strongly biased toward 3° C-H bonds even in systems possessing a significantly greater number of methylene groups. In addition, the benzoxathiazine catalyst is effective for epoxidation of terminal and electron-deficient olefins. Collectively, these findings represent an important first step toward the advancement of general methodology for selective C-H oxidation. Copyright
Prodrugs: Part 3. 2-Formylphenyl esters of indomethacin, ketoprofen and ibuprofen and 6-substituted 2-formyl and 2-acylphenyl esters of aspirin
Abordo, Evelyn A.,Bowden, Keith,Huntington, Anthony P.,Powell, Sarah L.
, p. 95 - 101 (2007/10/03)
The synthesis and study of a novel series of potential prodrugs of indomethacin, ketoprofen, ibuprofen and aspirin are reported. 2-Formylphenyl esters of the NSAIDs, together with two 6-substituted 2-formyl and two 2-acylphenyl aspirins and 4-formylphenyl indomethacin, have been prepared. A study of their alkaline and neutral hydrolysis shows that these compounds, with the exception of 2-acetylphenyl aspirin, act as true prodrugs of the NSAIDs, giving the NSAID and acylphenol. The rates of hydrolysis and activation parameters indicate that the 2-acylphenyl esters employ an intramolecular catalytic route. The 2-formylphenyl esters were more potent as anti-inflammatory agents than the parent compounds in the carragheenan-induced paw oedema test.
