- Preparation of monoalkylpiperidines via the mild hydrogenation of monoalkynylpyridines
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Monoalkynylpyridines were prepared via a Sonogashira cross-coupling reaction between monoiodopyridines and alkynes. Mild hydrogenation of the obtained monoalkynylpyridines was then conducted to produce the corresponding monoalkylpiperidines in moderate to excellent yields. The hydrogenation reaction was carried out under H2 (1?atm) in the presence of 10?wt% Pd/C (5?eq) in either AcOH or MeOH at room temperature. The present mild method is therefore useful for the quick and easy preparation of monoalkylpiperidines.
- Usuki, Toyonobu,Komatsu, Akira
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Read Online
- METHOD FOR PRODUCING PIPERIDINE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a piperidine compound in an industrially convenient manner. SOLUTION: This invention relates to a method for producing a compound represented by general formula (I) or a salt thereof that includes the step of converting a pyridine compound having an alkynylene group in a side chain, by a contact hydrogenation reaction, into the compound represented by general formula (I) or a salt thereof (in the general formula (I), R1 is a hydrogen atom, a hydroxy group, or an optionally substituted alkyl group having carbon atoms of 1 or more and 20 or less). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0053-0055
(2018/04/18)
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- An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer
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A number of indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of redu
- Colley, Helen E.,Muthana, Munitta,Danson, Sarah J.,Jackson, Lucinda V.,Brett, Matthew L.,Harrison, Joanne,Coole, Sean F.,Mason, Daniel P.,Jennings, Luke R.,Wong, Melanie,Tulasi, Vamshi,Norman, Dennis,Lockey, Peter M.,Williams, Lynne,Dossetter, Alexander G.,Griffen, Edward J.,Thompson, Mark J.
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p. 9309 - 9333
(2015/12/23)
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- Rhodium(III)-catalyzed isoquinolone synthesis: The N-O bond as a handle for C-N bond formation and catalyst turnover
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An external-oxidant-free process to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion. Mechanistic studies point out the important involvement of a N-O bond as a tool for C-N bond formation and catalyst turnover.
- Guimond, Nicolas,Gouliaras, Christina,Fagnou, Keith
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supporting information; experimental part
p. 6908 - 6909
(2010/07/05)
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- SUBSTITUTED OXADIAZOLE DERIVATIVES AS S1P AGONISTS IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISEASES
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[00180] Disclosed are compounds of Formula (I) or pharmaceutically acceptable salts thereof, wherein Q is or R1 is cycloalkyl, heteroaryl, or heterocyclyl, each optionally substituted with one to five substituents independently selected from C1 to C6 alkyl, C1 to C4 haloalkyl, -OR4, and/or halogen; and R2, R3, R4, and n are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as vascular disease and autoimmune diseases.
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Page/Page column 60-61
(2010/08/08)
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- Highly flexible synthesis of 2-arylethylamine derivatives
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A new and highly flexible procedure for the synthesis of 2-arylethylamine derivatives is described. By the new procedure, the target compounds can be synthesized with high diversity in three steps from aryl halides, terminal alkynes, and primary amines. T
- Siebeneicher, Holger,Doye, Sven
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p. 1213 - 1220
(2007/10/03)
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- A Nickel-catalyzed carbozincation of aryl-substituted alkynes
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The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)2 in THF:NMP mixtures produces syn-carbozincation products with good to excellent regio- and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z:E > 99:1) has been developed.
- Stuedemann, Thomas,Ibrahim-Ouali, Malika,Knochel, Paul
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p. 1299 - 1316
(2007/10/03)
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