- PREPARATION OF AN α,β-TYPE OF TER- AND SEPTITHIOPHENES
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An α,β-type of thiophenes oligomers, 2,3':4',2"-terthiophene and 2,3':4',2'':5'',3''':4''',2'''':5'''',3''''':4''''',2''''''-septithiophene, were synthesized through intramolecular reductive coupling reaction of diketo sulfides with a low-valent titanium reagent.
- Nakayama, Juzo,Murabayashi, Shigeru,Hoshino, Masamatsu
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Read Online
- Synthesis method of 2-thiopheneacetic acid
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The invention provides a synthesis method of 2-thiopheneacetic acid, which is characterized by comprising the following steps: (1) acylation reaction: carrying out Friedel-Crafts reaction on thiopheneand 2-chloroacetyl chloride as raw materials to obtain 2-chloroacetyl thiophene; and (2) rearrangement reaction: carrying out a Favanskii rearrangement reaction on the 2-chloroacetyl thiophene underan alkaline condition to obtain the 2-thiopheneacetic acid. The method is wide in raw material source, low in cost, few in steps, simple to operate, high in safety, small in pollution and easy to industrialize. Friedel-Crafts reaction and Favanskii rearrangement reaction are adopted, the conversion rate of the two reactions is high, the selectivity is good, the operation of the reaction process issimple, no special reagent is needed, the raw materials are cheap and easy to obtain, the requirement for equipment is not high, the product yield is high, few impurities are contained, and the method has remarkable advantages and practical value.
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Paragraph 0017; 0046-0047; 0049-0050; 0052-0053
(2020/06/17)
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- Iridium-Catalyzed Asymmetric Hydrogenation of Halogenated Ketones for the Efficient Construction of Chiral Halohydrins
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Iridium-catalyzed asymmetric hydrogenation of prochiral halogenated ketones was successfully developed to prepare various chiral halohydrins with high reactivities and excellent enantioselectivities under basic reaction condition (up to >99% conversion, 99% yield, >99% ee). Moreover, gram-scale experiment was performed well in the presence of just 0.005 mol% (S/C=20 000) Ir/f-amphox catalyst with 99% yield and >99% ee. (Figure presented.).
- Yin, Congcong,Wu, Weilong,Hu, Yang,Tan, Xuefeng,You, Cai,Liu, Yuanhua,Chen, Ziyi,Dong, Xiu-Qin,Zhang, Xumu
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supporting information
p. 2119 - 2124
(2018/04/30)
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- NOVEL PYRIDINIUM COMPOUNDS
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The present invention relates to novel pyridinium compounds, their isomers, steroisomers, atropisomers, conformers, tautomers, polymorphs, hydrates and solvates. The present invention also encompasses process for preparing novel compounds and pharmaceutical composition of said compounds. The invention further relates to the use of the above mentioned compounds for the preparation of medicament for use as pharmaceuticals.
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Page/Page column 22; 23
(2016/10/31)
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- The α-chlorination of aryl methyl ketones under aerobic oxidative conditions
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The novel reaction system air/ammonium nitrate/iodine/hydrochloric acid [air/NH4NO3(cat.)/I2(cat.)/HCl] is introduced as a simple, safe, cheap, efficient and regioselective mediator for the α-chlorination of aryl, heteroaryl and alkyl methyl ketones under aerobic oxidative conditions. The inventive use of a catalytic amount of iodine enabled the moderate to quantitative, regioselective chlorination of a comprehensive scope of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents, some of which possess declared potential biological and pharmaceutical activity. Air oxygen under a slight overpressure plays the role of the terminal oxidant catalytically activated by redox cycles of nitrogen oxides released from the catalytic amount of ammonium nitrate (NH4NO3) under acidic conditions of hydrochloric acid (HCl) and co-catalyzed by elemental iodine (I2), which was found to be essential for the high efficiency of the reaction system.
- Prebil, Rok,Stavber, Stojan
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supporting information
p. 1266 - 1274
(2014/05/06)
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- Enantioselective synthesis of heteroaromatic epoxyketones under phase-transfer catalysis using D-glucose- and D-mannose-based crown ethers
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Heteroaromatic epoxyketones have been synthesized in an asymmetric Darzens condensation of 2-chloroacetylfuran or 2- and 3-chloroacetylthiophene with aromatic aldehydes and in the enantioselective epoxidation of α,β-enones with an N-methylpyrrole unit, in
- Rapi, Zsolt,Szabo, Tamas,Keglevich, Gyoergy,Szxoellosy, Aron,Drahos, Laszlo,Bako, Peter
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body text
p. 1189 - 1196
(2011/10/19)
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- Thienylhalomethylketones: Irreversible glycogen synthase kinase 3 inhibitors as useful pharmacological tools
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Thienylhalomethylketones, whose chemical, biological, and pharmaceutical data are here reported, are the first irreversible inhibitors of GSK-3β described to date. Their inhibitory activity is likely related to the cysteine residue present in the ATP-binding site, which is proposed as a relevant residue for modulation of GSK-3 activity. The good cell permeability of the compounds allows them to be used in different cell models. Overall, the results presented here support the potential use of halomethylketones as pharmacological tools for the study of GSK-3β functions and suggest a new mechanism for GSK-3β inhibition that may be considered for further drug design.
- Perez, Daniel I.,Conde, Santiago,Perez, Concepcion,Gil, Carmen,Simon, Diana,Wandosell, Francisco,Moreno, Francisco J.,Gelpi, Jose L.,Luque, Francisco J.,Martinez, Ana
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scheme or table
p. 6914 - 6925
(2010/02/28)
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- Novel building blocks: 1-Aryl-2-chloro-1-ethoxyethenes - Preparations and transformations
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We described here a simple method for the preparation of 1-aryl-2-chloro-1-ethoxyethenes 2a-u, which are prodrugs for Alzheimer's disease, by the reaction of dichloroacetaldehyde diethyl acetal with various aryl and alkenyllithium compounds in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Yoshimatsu, Mitsuhiro,Sakai, Miho,Moriura, Eri
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p. 498 - 507
(2008/02/06)
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- 3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE AND THIAZINE DERIVATIVES AS CETP INHIBITORS
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The invention is directed to compounds of Formula (I) described herein useful as CETP inhibitors, compositions containing them, and methods of using them.
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Page/Page column 106
(2008/06/13)
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- Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols
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As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones.
- Tanis, Steven P.,Evans, Bruce R.,Nieman, James A.,Parker, Timothy T.,Taylor, Wendy D.,Heasley, Steven E.,Herrinton, Paul M.,Perrault, William R.,Hohler, Richard A.,Dolak, Lester A.,Hester, Matthew R.,Seest, Eric P.
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p. 2154 - 2182
(2007/10/03)
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- Efficient microwave induced direct α-halogenation of carbonyl compounds
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A novel and direct method for the synthesis of α-halocarbonyl compounds using sequential treatment of carbonyl compounds with [hydroxy(tosyloxy)iodo]benzene followed by magnesium halides under solvent-free microwave irradiation conditions is described.
- Lee, Jong Chan,Park, Jin Young,Yoon, So Young,Bae, Yong Hun,Lee, Seung Jun
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p. 191 - 193
(2007/10/03)
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- Pyridoquinoxaline antivirals
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The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof wherein R1, R2 and R3 are as defined in the specification. The compounds are useful for the treatment of viral infections.
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- Chemoenzymatic synthesis of duloxetine and its enantiomer: Lipase-catalyzed resolution of 3-hydroxy-3-(2-thienyl) propanenitrile
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An efficient and facile chemoenzymatic synthesis of duloxetine by lipase mediated resolution of 3-hydroxy-3-(2-thienyl)propanenitrile has been achieved. This process also describes an enantioconvergent synthesis of duloxetine via a Mitsunobu reaction.
- Kamal, Ahmed,Khanna, G. B. Ramesh,Ramu,Krishnaji
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p. 4783 - 4787
(2007/10/03)
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- Compounds and their therapeutic use
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Compounds of formula I: [wherein: X represents —CH═CH—, —CH═CR—, —CR═CR—, —CO—, —O—, —NH—, —NR—, S—, —SO—, —SO2—, —CH═N—, —CR═N—, —CH═N(O)—, —CR═N(O)— or any other atom or group of atoms capable of forming a S— or 6-membered heterocyclic ring;
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- Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry
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A series of CCK-B/gastrin receptor antagonists, 2,4-dioxo-1,5-benzodiazepine derivatives with a plane of symmetry, were designed, synthesized, and evaluated for antagonistic activity. Structure-activity relationship studies revealed that carbonylmethyl groups at both N-1 and N-5 positions and hydrophilic groups, such as the carboxyl group on the benzene ring attached to the ureido group at the C-3 position, brought about potent affinity and subtype selectivity for CCK-B/gastrin receptors. Several compounds showed excellent in vivo inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats.
- Hagishita, Sanji,Seno, Kaoru,Kamata, Susumu,Haga, Nobuhiro,Ishihara, Yasunobu,Ishikawa, Michio,Shimamura, Mayumi
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p. 1433 - 1446
(2007/10/03)
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- An easy synthesis of 2-haloacetylfurans and -thiophenes
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The 2-chloro (or bromo)acetylfurans and -thiophenes were selectively synthesized with preservation of the heteroaromatic cycle from enoxysilane forms of 2-acetylfurane and -thiophene.
- Dubac,Gaset,Maraval
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- α-Chlorination of Aromatic Acetyl Derivatives with Benzyltrimethylammonium Dichloroiodate
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Reaction of aromatic acetyl derivatives with benzyltrimethylammonium dichloroiodate in refluxing dichloroethane/methanol for several hours gave α-chloroacetyl derivatives in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Fujisaki, Shizuo,Maeno, Kimihiro,Okamoto, Tsuyoshi
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p. 545 - 546
(2007/10/02)
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- Pyridazine derivatives having a psychotropic action and compositions
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This invention relates to pyridazine derivatives substituted in the 4-position by a cyano group having psychotropic activity. It also relates to a process for the preparation of these products and their application as medicaments. STR1
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- Reaction of Phosphorus Pentachloride with 2-Acetylthiophene and Acetophenone
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The treatment of 2-acetylthiophene with PCl5, followed by dehydrochlorination, is known to be a poor method for synthesizing 2-ethynylthiophene (1a).Reinvestigation of the reaction showed the major products to be the E- and Z- isomers of 1,2-dichloro-1-(2-thienyl)ethylene (7a), with minor amounts of 1,1-dichloro-1-(2-thienyl)ethane (3a), 1-chloro-1-(2-thienyl)ethylene (4a), 2-(chloroacetyl)thiophene, and 2-(dichloroacetyl)thiophene.The treatment of acetophenone with PCl5 yielded similar products, and the mechanism of these reactions is discussed.The major product 7a could be converted into 1a by reaction with magnesium.The yield of 4a was increased when pyridine was also used, when only 1 equiv of PCl5 was added by portions to the ketone, or when catecholphosphorus trichloride was used instead of PCl5.The best method for converting 2-acetylthiophene into 1a goes through the enol phosphonate of 2-(bromoacetyl)thiophene, which is treated with sodium amide.
- Kagan, Jaques,Arora, Sudershan K.,Bryzgis, Marius,Dhawan, Som N.,Reid, Kevin,et al.
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p. 703 - 706
(2007/10/02)
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