76429-68-0Relevant academic research and scientific papers
Selective Hydrogenation of Benzofurans Using Ruthenium Nanoparticles in Lewis Acid-Modified Ruthenium-Supported Ionic Liquid Phases
Bordet, Alexis,El Sayed, Sami,Hetaba, Walid,Leitner, Walter,Luska, Kylie L.,Weidenthaler, Claudia
, p. 2124 - 2130 (2020/02/11)
Ruthenium nanoparticles immobilized on a Lewis-acid-functionalized supported ionic liquid phase (Ru?SILP-LA) act as effective catalysts for the selective hydrogenation of benzofuran derivatives to dihydrobenzofurans. The individual components (nanoparticles, chlorozincate-based Lewis-acid, ionic liquid, support) of the catalytic system are assembled using a molecular approach to bring metal and acid sites in close contact on the support material, allowing the hydrogenation of O-containing heteroaromatic rings while keeping the aromaticity of C6-rings intact. The chlorozincate species were identified to be predominantly [ZnCl4]2- anions using X-ray photoelectron spectroscopy and are in close interaction with the metal nanoparticles. The Ru?SILP-[ZnCl4]2- catalyst exhibited high activity, selectivity, and stability for the catalytic hydrogenation of a variety of substituted benzofurans, providing easy access to biologically relevant dihydrobenzofuran motifs under continuous flow conditions.
Trimethylphosphate as a Methylating Agent for Cross Coupling: A Slow-Release Mechanism for the Methylation of Arylboronic Esters
He, Zhi-Tao,Li, Haoquan,Haydl, Alexander M.,Whiteker, Gregory T.,Hartwig, John F.
supporting information, p. 17197 - 17202 (2018/12/14)
A methyl group on an arene, despite its small size, can have a profound influence on biologically active molecules. Typical methods to form a methylarene involve strong nucleophiles or strong and often toxic electrophiles. We report a strategy for a new, highly efficient, copper and iodide co-catalyzed methylation of aryl- and heteroarylboronic esters with the mild, nontoxic reagent trimethylphosphate, which has not been used previously in coupling reactions. We show that it reacts in all cases tested in yields that are higher than those of analogous copper-catalyzed reactions of MeOTs or MeI. The combination of C-H borylation and this methylation with trimethylphosphate provides a new approach to the functionalization of inert C-H bonds and is illustrated by late-stage methylation of four medicinally active compounds. In addition, reaction on a 200 mmol scale demonstrates reliability of this method. Mechanistic studies show that the reaction occurs by a slow release of methyl iodide by reaction of PO(OMe)3 with iodide catalyst, rather than the typical direct oxidative addition to a metal center. The low concentration of the reactive electrophile enables selective reaction with an arylcopper intermediate, rather than nucleophilic groups on the arylboronate, and binding of tert-butoxide to the boronate inhibits reaction of the electrophile with the tert-butoxide activator to form methyl ether.
CERTAIN PROTEIN KINASE INHIBITORS
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Paragraph 0633; 0634, (2014/05/20)
Disclosed herein are protein kinase inhibitors, more particu-larly novel pyrimidine derivatives and pharmaceutical com-positions thereof, and method of use thereof
GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF
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Page/Page column 138, (2010/02/07)
Compounds of Formula (IA) and Formula (IB) wherein R1, R2, R3, R4, R5, and R6 are as defined herein for Formula (IA) or Formula (IB), or a tautomer, prodrug, solvate,or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.
PHOTOCHEMICAL BEHAVIOUR OF 3,4-EPOXYPRECOCENE-I AND RELATED EPOXYCHROMANS
Ariamala, G.,Balasubramanian, K. K.
, p. 3769 - 3774 (2007/10/02)
A systematic study of photochemical behaviour of 3,4-epoxyprecocene-I and related epoxychromans was undertaken.Upon irradiation in acetone or cyclohexane, 3,4-epoxyprecocene-I 1 was found to undergo photoisomerisation to the corresponding 3-chromanone 2.In contrast, the photochemical behaviour of analogous 3,4-dihydro-3,4-epoxy-2H-1-benzopyrans 3 was found to be dependent upon the nature of solvent.Irradiation of 3 in cyclohexane led to photodecarbonylation leading to the formation of 2,3-dihydrobenzofurans 4, whereas irradiation in acetone resulted in the formation of chromanones 5.
Oxygen Heterocycles by the Parham Cyclialkylation
Bradsher, Charles K.,Reames, David C.
, p. 1384 - 1388 (2007/10/02)
The addition of butyllithium at -100 deg C to ω-bromoalkyl ethers of o-bromophenol (and its congeners) led to preferential exchange of the aryl bromine at position 2.The resulting organolithium reagents, under suitable conditions, cyclized to afford 2,3-dihydrobenzofurans (6), 3,4-dihydro-2H-1-benzopyrans (13), or 2,3,4,5-tetrahydro-1-benzoxepins (16) in good yields, but less satisfactory results were obtained with the intermediate expected to produce 8-methyl-3,4,5,6-tetrahydro-2H-1-benzoxocin (19). ω-Bromoethyl and ω-bromopropyl ethers of suitable dibromophenols were treated successively with 2 equiv of butyllithium and an electrophile to yield derivatives of 6 and 13.
