17100-66-2Relevant academic research and scientific papers
Improved Hiyama cross-coupling reactions using HOMSi
Marcuccio, Sebastian M.,Epa, Ruwan,Moslmani, Maisa,Hughes, Andrew B.
, p. 7178 - 7181 (2011)
Various parameters in the Hiyama cross-coupling reaction of HOMSi reagents with ethyl bromobenzoate were studied. These included solvent, ligand, palladium source, and added water. DMF and THF were found to be excellent solvents. Palladium chloride was found to be the best palladium source and no added water was required. The use of tri-o-tolylphosphine as the ligand proved to be particularly effective.
KRAS G12C INHIBITORS
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Paragraph 0393-0394, (2020/03/23)
The present invention relates to compounds that, inhibit KRas G12C, In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
Macrocyclic Modulators of the Ghrelin Receptor
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Paragraph 0419; 0420, (2018/05/03)
The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.
Synthesis, Reactivity, Functionalization, and ADMET Properties of Silicon-Containing Nitrogen Heterocycles
Barraza, Scott J.,Denmark, Scott E.
supporting information, p. 6668 - 6684 (2018/06/12)
Silicon-containing compounds have been largely ignored in drug design and development, despite their potential to improve not only the potency but also the physicochemical and ADMET (absorption, distribution, metabolism, excretion, toxicity) properties of drug-like candidates because of the unique characteristics of silicon. This deficiency is in large part attributable to a lack of general methods for synthesizing diverse organosilicon structures. Accordingly, a new building block strategy has been developed that diverges from traditional approaches to incorporation of silicon into drug candidates. Flexible, multi-gram-scale syntheses of silicon-containing tetrahydroquinoline and tetrahydroisoquinoline building blocks are described, along with methods by which diversely functionalized silicon-containing nitrogen heterocycles can be rapidly built using common reactions optimized to accommodate the properties of silicon. Furthermore, to better clarify the liabilities and advantages of silicon incorporation, select compounds and their carbon analogues were challenged in ADMET-focused biological studies.
Indium Catalyzed Hydrofunctionalization of Styrene Derivatives Bearing a Hydroxy Group with Organosilicon Nucleophiles
Kita, Yuji,Yata, Tetsuji,Nishimoto, Yoshihiro,Yasuda, Makoto
, p. 740 - 753 (2018/01/28)
Hydrofunctionalization is one of the most important transformation reactions of alkenes. Herein, we describe the development of an indium-triiodide-catalyzed hydrofunctionalization of alkenes bearing a hydroxy group using various types of organosilicon nucleophiles. Indium triiodide was the most effective catalyst, whereas typical Lewis acids such as TiCl4, AlCl3, and BF3·OEt2 were ineffective. Many functional groups were successfully introduced, and these resulted in yields of 31-86%. Various styrene derivatives were also applicable to this reaction. Mechanistic investigation revealed that the present hydrofunctionalization proceeded through Br?nsted acid-catalyzed intramolecular hydroalkoxylation of alkenes followed by InI3-catalyzed substitution reaction of cyclic ether intermediates.
Selective tetrahydropyranylation of alcohols and phenols using titanium(IV) salophen trifluoromethanesulfonate as an efficient catalyst
Yadegari, Maryam,Moghadam, Majid
, p. 872 - 875 (2016/09/20)
Titanium(IV) salophen trifluoromethanesulfonate, [TiIV(salophen)(OSO2CF3)2], as a catalyst enables selective tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran. Using this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to their corresponding tetrahydropyranyl ethers in high yields and short reaction times at room temperature. Investigation of the chemoselectivity of this method showed discrimination between the activity of primary alcohols in the presence of secondary and tertiary alcohols and phenols. This heterogenized catalyst could be reused several times without loss of its catalytic activity. Copyright
P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
Shirini, Farhad,Fallah-Shojaei, Abdollah,Abedini, Masoumeh,Samavi, Laleh
, p. 1699 - 1712 (2016/07/27)
P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.
Highly efficient chiral polydentate sulfinyl ligands/catalysts containing prolinol moiety
Chrzanowski, Jacek,Rachwalski, Michal,Pieczonka, Adam M.,Leniak, Stanislaw,Drabowicz, Jzef,Kielbasiski, Piotr
, p. 2649 - 2655 (2016/05/10)
New polydentate chiral ligands, containing the hydroxyl group, stereogenic sulfinyl group and enantiomeric prolinol moieties were synthesized and proved very efficient catalysts in the asymmetric diethylzinc addition to benzaldehyde, the asymmetric aldol
Introduction of a New Ionic Liquid Catalyst for the Trimethylsilyl and Tetrahydropyranyl Protection of Alcohols
Shirini, Farhad,Abedini, Masoumeh,Mahmoodi, Nosratollah,Biglari, Mohammad,Safarpoor Nikoo Langrudi, Mohaddeseh
, p. 1912 - 1921 (2015/12/12)
1,1'-Disulfo-[2,2'-bipyridine]-1,1'-hydrogen sulfate, BiPy(SO3H)2(HSO4)2, is prepared and identified as a new ionic liquid. This reagent was used for the promotion of the chemoselective trimethylsilyl and tetrahydropyranyl protection of alcohols. All reactions were performed under mild reaction conditions in high to excellent yields. Ease of the preparation of the heterogeneous catalyst, simplicity and easy work-up procedure, high reaction rates, and recyclability and reusability of the catalyst are the main advantages of this method.
Straightforward synthesis of HOMSi reagents via sp2 C-H silylation
Minami, Yasunori,Komiyama, Takeshi,Hiyama, Tamejiro
supporting information, p. 1053 - 1055 (2015/09/02)
Straightforward C-H silylation of heteroarenes and alkenes was found to provide efficient access to organo-HOMSi reagents as stable silicon reagents for cross-coupling. Various heteroarenes and terminal alkenes were silylated to show the versatility of the reaction. This method was applied in double silylation reactions to give bisHOMSi reagents. The silylation products could be used in the cross-coupling reaction with haloarenes easily.
