- Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors
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A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzyl-amines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10?2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).
- Polyanskii, Kirill B.,Alekseeva, Kseniia A.,Raspertov, Pavel V.,Kumandin, Pavel A.,Nikitina, Eugeniya V.,Gurbanov, Atash V.,Zubkov, Fedor I.
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supporting information
p. 769 - 779
(2019/04/17)
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- C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF
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This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.
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- Preparation of conformationally constrained α2 antagonists: The bicyclo[3.1.0]hexane approach
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The aim of the research was to discover antagonists at α2 receptor subtypes potentially more selective than known compounds. We focused on new, conformationally restricted analogues of atipamezole. The key step in the synthetic sequences leading to target compounds relied on a rhodium-catalyzed intramolecular cyclopropanation reaction, the outcome of which varied with the nature of the diazo styrene precursor. Thus, depending on the substitution pattern of the double bond and the electronic properties of the diazo precursors, the cyclopropanes 2 or 7, naphtalenes 8, or pyrazolines 17 were formed. The byproducts 8 and 17 originated from different, nonoverlapping mechanisms. Among the racemates synthesized, three compounds (1a, 22a, and 22b) showed increased selectivity for α2A vs. α2B and α2C receptor subtypes, and consequently were prepared in enantiomerically pure form. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Bonnaud, Bernard,Funes, Philippe,Jubault, Nathalie,Vacher, Bernard
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p. 3360 - 3369
(2007/10/03)
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- Determining the scope of the lanthanide mediated, sequential hydroamination/C-C cyclization reaction: Formation of tricyclic and tetracyclic aromatic nitrogen heterocycles
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The scope of the lanthanide mediated, sequential hydroamination/C-C cyclization reaction was determined for the formation of tricyclic and tetracyclic aromatic nitrogen heterocycles. An array of ring sizes was explored to determine the diastereoselectivity. The electronic characteristics of the aromatic ring was also varied to determine how it affected the cascade reaction. It was found that the benzo[a]quinolizine and the pyrido[2,1,a]isoindolizine ring systems formed with the highest diastereoselectivity (>20:1), regardless of the electronic characteristics of the aromatic ring. Additionally, a tetracyclic indole nitrogen heterocycle was formed with a 2.3:1 diastereomeric ratio. A novel procedure for substrate preparation is also presented.
- Molander, Gary A.,Pack, Shawn K.
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p. 10581 - 10591
(2007/10/03)
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- Mascara comprising solid particles
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A composition for coating keratinous fibers, comprising, in a cosmetically acceptable medium comprising at least one volatile solvent, a nonvolatile fraction comprising: a) at least one polymer capable of adhering to the keratinous fibers, b) particles which are solid at 25° C. chosen from: i) solid particles of a crystalline or semicrystalline material, ii) solid particles of an amorphous material, iii) solid particles of at least one wax having a hardness of greater than or equal to 6.5 MPa iv) and mixtures thereof. The solid particles are present in the composition in an amount such that the volume fraction of the solid particles is less than or equal to 50% of the total volume of the said nonvolatile fraction. The composition can make it possible to obtain good curling of keratinous fibers, such as eyelashes.
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- MERCAPTOACETYLAMIDO 1,3,4,5-TETRAHYDRO-BENZO[C]AZEPIN-3-ONE DISULFIDE DERIVATIVES USEFUL AS INHIBITORS OF ENKEPHALINASE AND ACE
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The present invention relates to certain novel mercaptoacetylamido 1,3, 4,5-tetrahydro-benzo[c]azepin-3-one disulfide derivatives of the formula STR1 useful as inhibitors of enkephalinase and of ACE.
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- The synthesis of aminobenzazepinones as anti-phenylalanine dipeptide mimics and their use in NEP inhibition
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A general and stereoselective synthesis of 4-aminobenzazepinones is presented. This peptidomimetic structure was used in the preparation of MDL 100,407, a potent inhibitor of NEP.
- Warshawsky, Alan M.,Flynn, Gary A.,Koehl, Jack R.,Mehdi, Shujaath,Vaz, Roy J.
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p. 957 - 962
(2007/10/03)
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- Polymerizable compound having mildew resistance and polymer thereof
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A novel mildew resistant polymerizable compound of the formula: STR1 wherein X is --0-- or --S--; and Y is a residue of a known mildew proofing compound, preferably, a residue of a compound selected from the group consisting of phenol substituted with 1 to 5 halogen atoms, p-chloro-m-cresol, o-phenylphenol, p-chloro-m-xylenol, salicylanilide, 8-hydroxyquinoline, 2-(4'-thiazolyl)benzimidazole, 2,5-dibromo-4-methylaniline, 1,2-benzoisothiazolin-3-one and 2-pyridinethiol-1-oxide. A polymer of the compound [I] and polyurethane composition containing the polymer are also disclosed.
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- Cycloadditions of 4-pyrones. An approach to colchicine
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The 4-pyrone, [5-acetoxy-4-oxo-4H-pyran-2-yl]carbonyl chloride was coupled with the malonate anion of bis(2,2,2-trichloroethyl) 2-ethenyl-3,4,5-trimethoxybenzylpropanedioate and analogs thereof. These adducts then underwent intramolecular thermal cyclizations (61-100% yield) to form the two fused seven member rings of the carbon skeleton of colchicine. The malonate moiety was deprotected and decarboxylated quantitatively to provide the desired ring system which contained a bridging ether, from C7a to C11 in the C ring, and a ketone at the 7 position. Removal of the bridging ether as H2O would yield the desired tropolone. Our attempts to remove the ether bridge were unsuccessful.
- McBride,Garst
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p. 2839 - 2854
(2007/10/02)
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- Electro-optical materials and light modulator devices containing same
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Azo-type optically active compounds and polymers are provided based on compounds of the general structure wherein aryl substituents are introduced which hinder or prohibit rotation around the single bonds of the --N=-- central moiety (as well as around certain other single bonds), to provide "planarized" structures having improved optically active properties, especially electro-optically active properties. These compounds and polymers find use in optically active waveguides.
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- Quaternary ammonium group-containing polymers having antimicrobial activity
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Polymeric quaternary ammonium compounds having recurring vinylbenzyl ammonium units are disclosed. The quaternary ammonium units preferably have 2 alkyl substituents of 1 to 4 carbons and 1 alkyl substituent of 4 to 12 carbons. These materials have antimicrobial properties and are particularly useful for preserving ophthalmic solutions.
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- FORMATION OF 1-CHLOROBENZOCYCLOBUTENE, ANTHRACENE OR BENZOFURAN BY FLASH VACUUM PYROLYSIS
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Pyrolysis of o-substituted benzylidene chlorides is shown to be a useful route to 1-chlorobenzocyclobutene, anthracene or benzofurans; evidence is given for a carbene intermediate in the pyrolysis of o-methoxybenzylidene chloride.
- Hussain, Amjad,Parrick, John
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p. 609 - 612
(2007/10/02)
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- Synthesis of the Benzotricyclo2,7>heptene Ring System via the Intramolecular -Cycloaddition Reaction of Some Cyclopropene Derivatives
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The photo and thermal reactions of a number of 1,2-diphenyl-3-methyl-3-(o-vinylphenyl)-substituted cyclopropenes have been studied.The thermolysis of these systems gave substituted benzotricyclo2,7> heptenes in good yield by means of a novel intramolecular cycloaddition.The sensitized di-?-methane photorearrangement of several substituted benzonorbornenes was used to independently synthesize the thermal cycloadducts.The observed regiospecificity of the rearrangement is understandable in terms of formation of the most stable diradical intermediate.In contrast to the thermal results, the photosensitized irradiation afforded a mixture of two products.In addition to the cycloadduct, a new compound was isolated whose formation involves attack of the ortho position of the triplet state on the terminal vinyl carbon followed by diradical coupling and subsequent rearomatization.Thermolysis or sensitized photolysis of several unsymmetrically substituted 1,3-diphenyl-2-methyl-2-(o-vinylphenyl)cyclopropenes afforded related cycloadducts.With these systems, the -cycloaddition reaction is highly regiospecific and involves bonding from the cyclopropene carbon bearing the methyl group onto the terminal vinyl carbon.The silver ion and singlet excited-state behavior of several substituted cyclopropenes was also studied, and the results obtained were compared to the reactions which occur on thermolysis or sensitized photolysis.
- Padwa, Albert,Rieker, William F.,Rosenthal, Robert J.
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p. 4446 - 4456
(2007/10/02)
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