- Perfluoroalkylation of imidazoles by electrochemically induced srn1 substitution
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Indirect electrochemical reduction, by means of aromatic anion radical mediators, of perfluoroalkyl halides in the presence of imidazolate or of substituted imidazolate anions yields the corresponding perfluoroalkylated imidazoles along an SRN1 mechanism.
- Medebielle, Maurice,Pinson, Jean,Saveant, Jean-Michel
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- HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF
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Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.
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Page/Page column 250
(2015/07/07)
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- FLUOROISOQUINOLINE SUBSTITUTED THIAZOLE COMPOUNDS AND METHODS OF USE
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The invention relates to thiazole compounds of Formula (I) and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such thiazole compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.
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Page/Page column 100
(2010/08/08)
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- ORGANIC COMPOUNDS
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The present invention provides a compound of formula I: said compound is inhibitor of aldosterone synthase (CYP11B2), and/or 11beta-hydroxylase (CYP11B1), and/or aromatase, and thus can be employed for the treatment of a disorder or disease mediated by al
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Page/Page column 127-128
(2008/12/06)
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- 3-dimethylhydrazono-1,1,1-trifluoro-2-propanone as a useful synthetic equivalent of trifluoropyruvaldehydeapplication to synthesis of fluorine-containing heterocycles
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3-Dimethylhydrazono-1,1,1-trifluoro-2-propanone (4) which is easily obtainable from formaldehyde dimethylhydrazone and trifluoroacetic anhydride was found to be an usuful synthetic equivalent of trifluoropyruvaldehyde for the synthesis of fluorine-containing heterocycles. With the use of 4, 4-trifluoromethylimidazoles and 2-trifluoromethylquinoxaline were successfully synthesized.
- Kamitori, Yasuhiro
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p. 1185 - 1190
(2007/10/03)
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- A convenient synthesis of perfluoroalkylated and fluorinated-aryl nitrogen bases by electrochemically induced SRN1 substitution
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Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl halides (CF3Br, n-C4F9I, n-C6F13I, I(CF2)4I) in the presence of imidazole, 4(5)-nitroimidazole, 2-methyl-5-nitroimidazole, 2-(4′-methoxyphenyl)imidazole, imidazole-2-carboxaldehyde, 4(5)-nitroimidazole-2-carboxaldehyde, 5(6)-nitrobenzimidazole, purines (adenine, hypoxanthine, xanthine, theophylline, lumazine) and pyrimidine anions (uracil, cytosine, barbituric acid) yields the corresponding C-perfluoroalkylated nitrogen bases by an SRN1 mechanism. Aromatic nucleophilic substitution of some fluorinated aryl halides 1-iodo-2-(trifluoromethyl)benzene and 1-(4′-iodo-tetrafluorophenyl)-imidazole was also investigated and it was found that 1-iodo-2-(trifluoromethyl)benzene could react successfully under redox-catalyzed conditions with imidazole, 2-(4′-methoxyphenyl)imidazole anion, and uracil anion to give the corresponding 5-(fluorinated-aryl) nitrogen bases. In the case of 1-(4′-iodo-tetrafluorophenyl)imidazole, direct electrochemical radical nucleophilic substitution with 2-methyl-5-nitroimidazole and uracil was possible in DMSO. In this way new, 4-[2′,3′,5′,6′-tetrafluoro-4′-(imidazol-1″- yl)phenyl] nitrogen bases were obtained in good yields.
- Medebielle, Maurice,Oturan, Mehmet Ali,Pinson, Jean,Saveant, Jean-Michel
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p. 1331 - 1339
(2007/10/03)
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- Photoinduced Electron-transfer Reaction of Difluorodiiodomethane with Azaaromatic Compounds and Enamines
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Irradiation of difluorodiiodomethane 1 with pyrroles, indole and imidazoles in dimethylformamide gives the corresponding trifluoromethylated products, whereas irradiation with enamines results in 2-trifluoromethyl ketones.A photoinduced electron-transfer mechanism is proposed.
- Chen, Qing-Yun,Li, Zhan-Ting
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p. 645 - 648
(2007/10/02)
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- Electrochemically Induced Nucleophilic Substitution of Perfluoroalkyl Halides. An Example of a Dissociative Electron-Transfer-Induced Chemical Reaction
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Nucleophilic substitution of perfluoroalkyl halides can be induced electrochemically.The reaction mechanism is a slightly modified version of the classical SRN1 mechanism in which the reaction is triggered by dissociative electron transfer, not
- Medebielle, Maurice,Pinson, Jean,Saveant, Jean-Michel
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p. 6872 - 6879
(2007/10/02)
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- Syntheses of Trifluoromethyl Heterocycles
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Mono and bicyclic heterocycles bearing trifluoromethyl substituent have been synthesized and characterized by spectral studies. 4(5)-Trifluoromethylimidazole (3) is prepared from the reaction of 3,3-dibromo-1,1,1-trifluoroacetone (2) with formaldehyde and ammonia.N-Methylation of 3 by phase transfer reaction gives 1-methyl-4-trifluoromethylimidazole (4). 2-Amino-4-trifluoromethylimidazole (5) is similarly obtained from 3-bromo-1,1,1-trifluoroacetone (1) and thiourea.The reaction of 1 with 2-aminopyridine and 2-aminothiazole gives 2-trifluoromethylimidazopyridine (7) and 6-trifluoromethylimidazothiazole (9) respectively.
- Moazzam, Muhammad,Parrick, J.
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p. 1051 - 1053
(2007/10/02)
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- Photochemical Perfluoroalkylation of Imidazoles
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Imidazole and its derivatives undergo facile trifluoromethylation or perfluoroalkylation, in methanol solution at ambient temperature, following radical dissociation of RFI by γ or UV irradiation.In the case of imidazole, attack occurs preferen
- Kimoto, Hiroshi,Fujii, Shozo,Cohen, Louis A.
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p. 2867 - 2872
(2007/10/02)
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- Trifluoromethylimidazoles and a method for their preparation
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4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammoni
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- 2-Pyrazinyl-trifluoromethylimidazoles and a method for their preparation
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4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammoni
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- 4-Trifluoromethylimidazoles and 5-(4-pyridyl)-1,2,4-triazoles, new classes of xanthine oxidase inhibitors.
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The syntheses of a number of 2-substituted 4-trifluoromethylimidazoles and 3-substituted 5-(4-pyridyl)-1,2,4-triazoles are described. The trifluoromethylimidazoles were prepared from 3,3-dibromo-1,1,1-trifluoroacetone after hydrolysis with aqueous sodium acetate solution and condensation with an aldehyde in the presence of ammonia. Basic hydrolysis of the trifluoromethyl group was found to provide a facile method for the synthesis of imidazole-4-carboxylic acids. In the imidazole series a 2-aryl substituent and a free imino group were required for xanthine oxidase inhibitory activity. The triazoles were obtained through the reaction of an aroylhydrazine and an imino ether followed by thermal ring closure of the intermediate acylamidrazone. As in the imidazole series, a free imino group is an absolute requirement for in vitro activity. Additional structure-activity relationships of these compounds are presented.
- Baldwin et al.
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