- Method for preparing piperidine compound by reducing pyridine compound through hydrogen transfer
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The invention discloses a method for preparing a piperazine compound through a hydrogen transfer reduction of a pyridine compound, belonging to the field of organic synthesis. Under mild conditions, pyridine derivatives are used as raw materials, oxazolidine is used as a hydrogen transfer reagent, and cheap transition metals such as copper, cobalt, silver, palladium and the like are used as catalysts for catalysis of a hydrogen transfer reaction on 1,2,3,4-substitution sites, so a series of hydrogen transfer reduction product piperidine compounds are prepared, wherein the oxazaborolidine is obtained by a reaction of amino acid with a tetrahydrofuran complex of borane. The method has the advantages that product yield is high, reaction conditions are mild, the general applicability of raw materials is good, a hydrogen transfer reagent is cheap and easy to obtain, and good reproducibility can still be shown after quantitative reaction is conudcted. Therefore, the method of the invention provides an effective scheme for the industrial production of other high-value compounds containing the structure in the future.
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Paragraph 0052; 0053; 0054; 0055; 0056
(2021/04/28)
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- Pd/C-catalyzed one-pot Suzuki-Miyaura cross-coupling/hydrogenation of pyridine derivatives
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Using bromopyridines and methoxyphenyl boronic acid as starting materials, consecutive Suzuki-Miyaura cross-coupling and hydrogenation reactions were undertaken using a heterogeneous Pd/C catalyst in one-pot manner under mild conditions (balloon-pressure at room temperature for hydrogenation) with excellent yield. To counter Pd leaching as well as catalyst poisoning, addition of an appropriate amount of H2O was crucial to achieving successful AcOH-promoted hydrogenation, which ensured a selective reduction of the pyridine rings to the corresponding piperidines.
- Pitna, Dinda B.,Tanaka, Nao,Usuki, Toyonobu
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- SUBSTITUTED METHYL PYRAZOLOPYRIMIDINONE AND METHYL IMIDAZOPYRAZINONE COMPOUNDS AS PDE1 INHIBITORS
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A chemical entity of Formula (I) or Formula (II): wherein Ra, Rb, Re, and Rf have any of the values described herein, and compositions comprising such chemical entities; methods of making them; and their use in
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Paragraph 0557
(2019/06/20)
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- BENZOTHIOPHENE ESTROGEN RECEPTOR MODULATORS
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This invention is a benzothiophene estrogen receptor modulator or its pharmaceutically acceptable salt or a pharmaceutically acceptable composition thereof to treat an estrogen-related medical disorder.
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Paragraph 0625-0626
(2018/08/29)
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- B(C6F5)3-Catalyzed Cascade Reduction of Pyridines
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B(C6F5)3 has been found to be an effective catalyst for reduction of pyridines and other electron-deficient N-heteroarenes with hydrosilanes (or hydroboranes) and amines as the reducing reagents. The success of this development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional-group tolerance (e.g. ketone, ester, unactivated olefins, nitro, nitrile, heterocycles, etc.) implies high practical utility.
- Liu, Zhi-Yun,Wen, Zhi-Hui,Wang, Xiao-Chen
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supporting information
p. 5817 - 5820
(2017/05/12)
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- The synthesis and evaluation of triazolopyrimidines as anti-tubercular agents
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We identified a di-substituted triazolopyrimidine with anti-tubercular activity against Mycobacterium tuberculosis. Three segments of the scaffold were examined rationally to establish a structure-activity relationship with the goal of improving potency and maintaining good physicochemical properties. A number of compounds displayed sub-micromolar activity against Mycobacterium tuberculosis with no cytotoxicity against eukaryotic cells. Non-substituted aromatic rings at C5 and a two-carbon chain connecting a terminal aromatic at C7 were preferred features; the presence of NH at C7 and a lack of substituent at C2 were essential for potency. We identified compounds with acceptable metabolic stability in rodent and human liver microsomes. Our findings suggest that the easily-synthesized triazolopyrimidines are a promising class of potent anti-tubercular agents and warrant further investigation in our search for new drugs to fight tuberculosis.
- Zuniga, Edison S.,Korkegian, Aaron,Mullen, Steven,Hembre, Erik J.,Ornstein, Paul L.,Cortez, Guillermo,Biswas, Kallolmay,Kumar, Naresh,Cramer, Jeffrey,Masquelin, Thierry,Hipskind, Philip A.,Odingo, Joshua,Parish, Tanya
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p. 3922 - 3946
(2017/07/05)
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- Selective NR2B Antagonists
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The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands of the NR2B receptor and may be useful for the treatment of various disorders of the c
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Paragraph 0158
(2015/07/15)
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- Concise synthesis of 3-arylpiperidines
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We present an easy and straightforward synthesis of 3-arylpiperidines by Grignard addition of piperidin-3-one with different arylmagnesium bromide reagents and acidic dehydroxylation of the resulting tertiary alcohol with the combination of triethylsilane and boron trifluoride etherate. This facile strategy was further used to synthesize preclamol. A highly regioselective dehydration of 3-arylpiperidin-3-ol with boron trifluoride etherate was investigated for preparing 3-aryl-1,4,5,6-tetrahydropyridine skeleton. A novel selenium dioxide mediated dihydroperoxidation of 3-aryl-1,4,5,6-tetrahydropyridine was also examined.
- Chang, Meng-Yang,Hsu, Ru-Ting,Chen, Hua-Ping,Lin, Pei-Jung
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p. 1173 - 1183
(2007/10/03)
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- 3-Phenylpiperidines. Central Dopamine-Autoreceptor Stimulating Activity
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Thirty compounds related to the selective dopamine-autoreceptor agonist 3-(3-hydroxyphenyl)-N-n-propylpiperidine have been synthesized and tested for central dopamine-autoreceptor stimulating activity.The 3-(3-hydroxyphenyl)piperidine moiety seems indispensable for high potency and selectivity.Introduction of an additional hydroxyl group into the 4-position of the aromatic ring gives a compound with dopaminergic activity but lacking selectivity for autoreceptors. 3-(3-Hydroxyphenyl)-N-n-propylpyrrolidine, 3-(3-hydroxy)-N-n-propylperhydroazepine, and 3-(3-hydroxyphenyl)quinuclidine were all inactive.The most potent compounds were the N-isopropyl-, N-n-butyl-, N-n-pentyl-, and N-phenethyl-substituted 3-(3-hydroxyphenyl)piperidine derivatives.None of the compounds investigated seemed to have central noradrenaline- or serotonin-receptor stimulating activity.
- Hacksell, Uli,Arvidsson, Lars-Erik,Svensson, Uno,Nilsson, J. Lars G.
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p. 1475 - 1482
(2007/10/02)
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