- Ligand assessment for the suzuki-miyaura cross coupling reaction of aryl and heteroaryl bromides with n-butylboronic acid. The advantages of buchwald's s-phos
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An investigation of biarylphosphine ligands for the Suzuki-Miyaura cross coupling reaction of aryl and heteroaryl bromides with n-butylboronic acid is presented. The results obtained on ligand modification and aryl as well as heteroaryl bromides variation represent a significant improvement in the state of the art of alkylboronic acid cross coupling methodology.
- Jagusch, Thomas,Lehnemann, Bernd,Meudt, Andreas,Nerdinger, Sven,Neuner, Sandro,Scherer, Stefan,Schottenberger, Herwig,Snieckus, Victor
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p. 631 - 644
(2020/01/31)
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- Structural development of liver X receptor (LXR) antagonists derived from thalidomide-related glucosidase inhibitors
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Following our previous discovery of LXR antagonistic activity of 2′-substituted phenylphthalimides derived from thalidomide-related glucosidase inhibitors, structure-activity studies and further structural development led to 5-chloro-N-2′-n-pentylphenyl-1,3-dithiophthalimide (5CPPSS-50), with IC50 values of about 10 and 13 μM for LXRα and LXR β, respectively.
- Noguchi-Yachide, Tomomi,Miyachi, Hiroyuki,Aoyama, Hiroshi,Aoyama, Atsushi,Makishima, Makoto,Hashimoto, Yuichi
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p. 1750 - 1754
(2008/09/17)
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- Synthesis of enantiopure 1-aryl-1-butylamines and 1-aryl-3-butenylamines by diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide
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The synthesis of enantiopure 1-aryl-1-butylamines via a highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. These are synthesised by a three-step procedure, which involves: (a) formation of the chiral imines; (b) asymmetric addition of the allylzinc reagent; (c) removal of the chiral auxiliary by means of a reductive or non-reductive method. The reductive method provides 1-aryl-1-butylamines whereas the non-reductive method preserves the double bond to afford 1-aryl-3-butenylamines. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Dalmolen, Jan,Van Der Sluis, Marcel,Nieuwenhuijzen, Jose W.,Meetsma, Auke,De Lange, Ben,Kaptein, Bernard,Kellogg, Richard M.,Broxterman, Quirinus B.
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p. 1544 - 1557
(2007/10/03)
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- Para-bromination of ortho-alkyl anilines
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A process of selectively preparing p-bromo-o-alkylanilines (e.g. 4-bromo-2-methylaniline) by reacting o-alkylanilines (e.g., 2-methylaniline) with unadsorbed bromine in a solvent selected from the group consisting of an inert di- tri- or tetrahaloaliphatic hydrocarbon (e.g., dichloromethane and dibromomethane), an alkyl nitrile (e.g., acetonitrile) and mixtures thereof.
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- Synthesis and Dediazoniation of 2-Butyl- and 2,5-Dibutylbenzenediazonium Ions
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2-Butylbenzenediazonium ion (1a) and 2,5-dibutylbenzenediazonium ion (1b) have been thermally decomposed in aqueous acid solution.In addition to the major product, the corresponding phenol, 5- and 6-membered ring products are formed (in a ratio of ca. 7:1) as well as products of elimination and substitution in the o-butyl group.The formation of the non-phenolic products is explained in terms of competing reactions of the initially formed aryl cations: cyclization by electrophilic atttack on the o-butyl group and 1,5-hydride ion transfer from the o-butyl group with concomitant elimination or reaction with the medium.Decompositions of 1a in the presence of copper(I) oxide, believed to generate aryl radicals, does not yield any measurable quantities of cyclized products, however.
- Sikkar, Rein,Martinson, Per
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p. 551 - 558
(2007/10/02)
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- Process for producing azasulfonium salts and rearrangement thereof to thio-ethers
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Preparing ortho-substituted anilines by reacting an N-chloroaniline with a non-carbonylic di-hydrocarbon sulfide to form an azasulfonium chloride, reacting the azasulfonium chloride with a strong base to form an aniline substituted in the 2-position with a hydrocarbon-S-hydrocarbyl thio-ether group. The ortho-substituted thio-ether compounds can be reduced with a de-sulfurizing reducing agent such as Raney nickel or the like to form the ortho-alkylated aniline. The aniline may be an amino-pyridine. The azasulfonium salt and thio-ether intermediate products can be isolated and recovered. If desired, the thio-ether compounds can be reduced to form ortho-alkylated aniline products which are useful as intermediates for a wide variety of purposes, including their uses in making dyes, herbicides, and the like.
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