- Synthesis of novel 2H,5H-dihydrofuran-3-yl ketones via ISNC reactions
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Unique 1-[2H,5H-dihydrofur-3-yl]ketones have been synthesized from propargylic nitroethers via intramolecular cycloadditions involving silyl nitronates. Various substituent groups were placed on the 2 and 5 positions of the dihydrofuran rings. We examined the scope of the long-range coupling in proton NMR of the oxo-dihydrofuran products. The identities of the diastereomers resulting from the Michael addition/cycloaddition reactions were tentatively assigned for the first time. CAChe MNDO PM5 and CONFLEX programs were engaged to assist with the identification of these stereoisomers. The reaction times and conditions for these oxo-dihydrofurans were found to be different than that of the published dihydrofuranals, which led us to propose a different mechanism.
- Grandbois, Matthew L.,Betsch, Kelsie J.,Buchanan, William D.,Duffy-Matzner, Jetty L.
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supporting information; scheme or table
p. 6446 - 6449
(2011/02/23)
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- Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents
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A stereoconvergent method for the catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic halides with arylzinc reagents has been developed. Neither family of compounds has previously been shown to be a suitable partner in such coupling processes. From a practical point of view, it is noteworthy that the catalyst components (NiCl2·glyme and pybox ligand 1) are commercially available. Copyright
- Smith, Sean W.,Fu, Gregory C.
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supporting information; experimental part
p. 12645 - 12647
(2009/05/09)
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- N-(3-(4-substituted-1-piperidinyl)-1-phenylpropyl) substituted sulfonamides as NK-3 receptor antagonists
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The present invention provides a method of treatment of a subject suffering from a disease, such as schizophrenia, for which the administration of an NK-3 antagonist is indicated which comprises administering to that subject a therapeutically effective amount of a compound of formula I: wherein, generally, Q is R1 is benzyl, phenyl, thiophene or imidazolyl optionally substituted with C1-4alkyl or halogen, such as methyl, fluorine or bromine; R2 is hydrogen or C1-4alkyl such as methyl; R3 is phenyl; R4 is hydrogen; R5 is hydrogen or C1-6alkylcarbonyl such as methylcarbonyl; X is —SO2— or —C(O)N(R2)SO2— where R2 is preferably hydrogen; Y is a bond, CH2 or Z1 where Z1 is —N(Rf)— in which Rf is C1-6alkylcarbonyl such as ethylcarbonyl; and R6 is phenyl, pyrazolyl, pyridyl, pyrimidinyl or benzimidazolonyl optionally substituted with one or two groups chosen from C1-6alkyl and benzyl, such as methyl, ethyl and benzyl; or a pharmaceutically acceptable salt thereof.
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Page/Page column 29
(2010/11/30)
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- Modulators of CCR5 chemokine receptor activity
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Compounds of Formula I: (wherein R1, R2, R3, R4, Q, and X are defined herein) are described. The compounds are modulators of CCR5 chemokine receptor activity. The compounds are useful, for example, in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
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- Chromium(II) Reagents; 1. Reduction of α-Acetylenic Ketones to trans-Enones
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The preparation and chromium(II)-induced reduction of twelve α-acetylenic ketones are reported.In general only trans-olefinic products were observed; the yields ranged from 40-84percent.A particular advantage of this protocol is its selectivity, thereby permitting use with a wide variety of functionalities.
- Smith, Amos B.,Levenberg, Patricia A.,Suits, Joan Z.
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p. 184 - 189
(2007/10/02)
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- Convenient deuterium labeling on a gas-liquid chromatography column. Preparative scale formation of α,β-unsaturated Od-alcohols
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Several α,β-unsaturated ethylenic and acetylenic alcohols 1-11 were conveniently deuterated on oxygen, by a GLC technique, with high yields and 80 to 98percent deuterium incorporation.
- Georgoulis, Constantin,Smadja, William,Ville, Guy
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p. 269 - 270
(2007/10/02)
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- Stereochemistry of Olefin and Fatty Acid Oxidation. Part 1. Autooxidation of Hexene and Hepta-2,5-diene Isomers
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The stereochemistry of the autooxidation of hex-1-ene, cis- and trans-hex-2-ene, cis- and trans-hex-3-ene, and of the three geometrical isomers of hepta-2,5-diene, has been determined by the reduction of the hydroperoxides produced and analysis of the resulting allylic alcohols.The relative proportions of the isomeric hydroperoxides are explicable in termes of the conformation of the parent olefins which are capable of giving delocalised radicals on hydrogen abstraction.
- Frankel, Edwin N.,Garwood, Robert F.,Vinson, John R.,Weedon, Basil C. L.
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p. 2707 - 2714
(2007/10/02)
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