- Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications
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Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.
- Engl, Sebastian,Reiser, Oliver
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p. 5581 - 5586
(2021/07/26)
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- Construction of azacycles by intramolecular amination of organoboronates and organobis(boronates)
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Intramolecular amination of organoboronates occurs with a 1,2-metalate shift of an aminoboron ate complex to form azetidines, pyrrolidines, and piperidines. Bis(boronates) undergo site-selective amination to form boronate-containing azacycles. Enantiomerically enriched azacycles are formed with high stereospecificity.
- Xu, Peilin,Zhang, Mingkai,Ingoglia, Bryan,Allais, Christophe,Dechert-Schmitt, Anne-Marie R.,Singer, Robert A.,Morken, James P.
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supporting information
p. 3379 - 3383
(2021/05/10)
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- 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 0027; 0028; 0029; 0030; 0031
(2021/04/28)
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- Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes
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We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ~ 1980) and chemoselectivity.
- Feng, Xuanyu,Song, Yang,Chen, Justin S.,Li, Zhe,Chen, Emily Y.,Kaufmann, Michael,Wang, Cheng,Lin, Wenbin
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p. 2193 - 2198
(2019/02/20)
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- Synthesis method for (R)-3-phenylpiperidine or/and (S)-3-phenylpiperidine and synthesis method for chiral intermediate of niraparib
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The invention belongs to the technical field of organic synthesis. The synthesis method firstly provided by the invention takes benzyl-4-oxopiperidine as a starting material, and the starting materialis subjected to Grignard reaction, elimination reaction, hydrogenation reduction reaction and chiral resolution in sequence to successfully obtain a target product (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine. The synthesis method sencondly provided by the invention takes the same starting raw material for Grignard reaction, organic silicon reagent is used for removing a hydroxide radical, and benzyl is removed by catalytic hydrogenation reaction; finally, the chiral resolution is carried out to obtain a target product. The (S)-3-phenylpiperidine can be synthesized according to the synthesis method. (S)-3-p-aminosalicylic phenylpiperidine can be synthesized according to the third aspect; or according to the fourth aspect, (S)-3-p-bromophenyl piperidine is synthesized to serve asthe key intermediate for preparing the niraparib. According to the synthesis method for (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine and the synthesis method for chiral intermediate of niraparib, production cost is obviously lowered, and the synthesis methods are favorable for the large-scale industrial production of a niraparib medicine.
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- Hydrogenation of Pyridines Using a Nitrogen-Modified Titania-Supported Cobalt Catalyst
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Novel heterogeneous catalysts were prepared by impregnation of titania with a solution of cobalt acetate/melamine and subsequent pyrolysis. The resulting materials show an unusual nitrogen-modified titanium structure through partial implementation of nitrogen into the support. The optimal catalyst displayed good activity and selectivity for challenging pyridine hydrogenation under acid free conditions in water as solvent.
- Chen, Feng,Li, Wu,Sahoo, Basudev,Kreyenschulte, Carsten,Agostini, Giovanni,Lund, Henrik,Junge, Kathrin,Beller, Matthias
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supporting information
p. 14488 - 14492
(2018/10/26)
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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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- Exploration of flexible phenylpropylurea scaffold as novel cardiac myosin activators for the treatment of systolic heart failure
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A series of flexible urea derivatives have been synthesized and demonstrated as selective cardiac myosin ATPase activator. Among them 1-phenethyl-3-(3-phenylpropyl)urea (1, cardiac myosin ATPase activation at 10?μM?=?51.1%; FS?=?18.90; EF?=?12.15) and 1-benzyl-3-(3-phenylpropyl)urea (9, cardiac myosin ATPase activation?=?53.3%; FS?=?30.04; EF?=?18.27) showed significant activity in?vitro and in?vivo. The change of phenyl ring with tetrahydropyran-4-yl moiety viz., 1-(3-phenylpropyl)-3-((tetrahydro-2H-pyran-4-yl)methyl)urea (14, cardiac myosin ATPase activation?=?81.4%; FS?=?20.50; EF?=?13.10), and morpholine moiety viz., 1-(2-morpholinoethyl)-3-(3-phenylpropyl)urea (21, cardiac myosin ATPase activation?=?44.0%; FS?=?24.79; EF?=?15.65), proved to be efficient to activate the cardiac myosin. The potent compounds 1, 9, 14 and 21 were found to be selective for cardiac myosin over skeletal and smooth myosins. Thus, these urea derivatives are potent scaffold to develop as a newer cardiac myosin activator for the treatment of systolic heart failure.
- Manickam, Manoj,Jalani, Hitesh B.,Pillaiyar, Thanigaimalai,Sharma, Niti,Boggu, Pulla Reddy,Venkateswararao, Eeda,Lee, You-Jung,Jeon, Eun-Seok,Jung, Sang-Hun
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p. 379 - 391
(2017/04/24)
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- Compounds with cardiac myosin activating function and pharmaceutical composition containing the same for treating or preventing heart failure
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The present invention relates to a compound having a cardiotonic activating function and a pharmaceutical composition containing the same. The composition comprising the compound according to the present invention is effective in preventing or treating heart failure. In addition, the compound is represented by chemical formula 2 or is pharmaceutically acceptable salt thereof.COPYRIGHT KIPO 2016
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Paragraph 0604-0606
(2017/02/02)
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- Catalytic hydrogenation of substituted pyridines with PtO2 catalyst
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The challenging methodology for the hydrogenation of substituted pyridines with mild reducing catalyst PtO2 in glacial acetic acid as a protic solvent using clean hydrogen under 50 to 70 bar atmospheric pressure leads to the synthesis of piperidine derivatives is reported. All the hydrogenated compounds were characterized by 1H NMR and ESI-MS.
- Sreenivasulu, Reddymasu,Ranganath, Kalluri Venkata Sri,Raju, Rudraraju Ramesh
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p. 4358 - 4360
(2015/11/28)
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- Compounds with cardiac myosin activating function and pharmaceutical composition containing the same for treating or preventing heart failure
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Disclosed are a compound having cardiotonic activity and a pharmaceutical composition containing the same, and the composition containing the compound, according to the present invention, is useful for preventing and treating heart failure.COPYRIGHT KIPO 2016
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Paragraph 0604-0608
(2016/10/07)
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- Synthesis and pharmacology of site-specific cocaine abuse treatment agents: Restricted rotation analogues of methylphenidate
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A series of threo-1-aza-3 or 4-substituted-5-phenyl[4.4.0]decanes (quinolizidines), which were envisioned as restricted rotational analogues (RRAs) of methylphenidate (MP), was synthesized and tested for inhibitory potency against [3H]WIN35,428, [3H]citalopram, and [ 3H]nisoxetine binding to the dopamine, serotonin, and norepinephrine transporters, respectively. Two different synthetic schemes were used; a Wittig reaction or acylation (followed by an intramolecular condensation) was a key feature of each scheme. The unsubstituted RRA, threo(trans)-1-aza-5-phenyl[4.4. 0]decane (12a), was equipotent to unconstrained threo-MP against [ 3H]WIN35,428 binding. The extra ring in these RRAs (which reduces the conformational freedom) and the orientation and polarity of substituents at the 4-position on this extra ring are of critical importance to the biological activity. Generally, the RRAs paralleled the corresponding unconstrained MP derivatives in binding affinity to the three transporters. The results suggest that the conformation of MP in which the carbonyl group of the methyl ester is H-bonded to the piperidinyl N-H may be the bioactive form of the molecule.
- Kim, Deog-Il,Deutsch, Howard M.,Ye, Xiaocong,Schweri, Margaret M.
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p. 2718 - 2731
(2008/02/04)
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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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- Rhodium-catalyzed intramolecular, anti-Markovnikov hydroamination. Synthesis of 3-arylpiperidines
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The intramolecular anti-Markovnikov hydroamination of 1-(3-aminopropyl)vinylarenes in the presence of a readily available rhodium catalyst to form 3-arylpiperidines is reported. In contrast to intermolecular hydroamination of vinylarenes, which occurred in high yields in the presence of rhodium catalysts containing DPEphos, the intramolecular reaction occurred in high yield in the presence of [Rh(COD)(DPPB)]BF4 as catalyst. Reactants with substituents β to the nitrogen occurred in high yield, and these reactions formed 3,5-disubstituted piperidines with high diastereomeric excess. The regiochemistry of these cyclizations contrasts with the regiochemistry of intramolecular hydroaminations catalyzed by lanthanide complexes, group III metal complexes, and platinum complexes, all of which have been reported to form cyclization products from Markovnikov addition. Copyright
- Takemiya, Akihiro,Hartwig, John F.
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p. 6042 - 6043
(2007/10/03)
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- PYRROLO[2,3-c]PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
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The present invention provides novel pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof, processes for the preparation thereof, and compositions comprising the same. The pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof of the present invention have excellent proton pump inhibition effects and possess the ability to attain a reversible proton pump inhibitory effect.
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Page/Page column 12
(2010/10/20)
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- Oximes and hydrazones that are useful in treating sexual dysfunction
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The present invention relates to oximes and hydrazones of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.
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Page/Page column 43
(2010/02/13)
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- Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase.
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The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.
- Musso, David L,Clarke, Morris J,Kelley, James L,Boswell, G Evan,Chen, Grace
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p. 498 - 506
(2007/10/03)
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- Probing the proposed phenyl-A region of the sigma-1 receptor.
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The proposed phenyl-A region of sigma (sigma) receptors accommodates several structural features. In this study we explored the possibility that appropriate structural features located at the phenyl-A region of sigma receptor sites could lead to more potent and selective agents for the sigma receptor subtypes. By keeping the phenyl-B substituent as the optimum omega-phenylpentyl moiety, and varying substituents in the phenyl-A region, we have observed changes in binding potency and selectivity at the sigma receptor subtypes. SAR for the binding of these compounds at sigma-2 sites was also examined.
- Ablordeppey, Seth Y,Fischer, James B,Law,Glennon, Richard A
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p. 2759 - 2765
(2007/10/03)
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- Synthesis and α-adrenergic and I1-imidazoline activity of 3- phenylpiperidines dimethyl-substituted on the phenyl ring
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In a previous study we found that certain 3-phenylpiperidines (PPEs, 5) display a good activity at α2-adrenergic receptors (α2-AR), whereas they are completely inactive at α1-AR. The PPEs 5 are conformationally restricted analogs of the corresponding adrenergic drug with a phenylethylamine structure (PAEs, 4) in which the benzylic hydroxyl group characteristic of the adrenergic catecholamines is not present. The most interesting of the PPEs proved to be the 3-(3,4-dimethylphenyl) substituted compound (5a) which had been found to be essentially inactive at β1- and β2-AR. The methyl groups present on the aromatic ring of 5a are found, albeit in a different position, on the phenyl of α2-adrenergic agonists with arylimidazolidine and arylimidazole structures. As such PPE 5a provided a unique template for the design of α2-AR ligands. On the basis of these premises, we synthesized all the possible dimethylphenyl-substituted isomers of PPE 5a. Their activity on α1- and α2-AR and on I1-imidazoline receptors (IR) was evaluated in vitro both by radioligand binding assays and by functional tests on isolated preparation. Two selected PPEs, 5a and 5f, were also tested for their affinity on α2-AR subtypes. Conformational studies were carried out by means of theoretical calculations, in order to rationalise the results of pharmacological tests at the molecular level.
- Macchia, Bruno,Bylund, David B.,Calderone, Vincenzo,Giannaccini, Gino,Lucacchini, Antonio,Macchia, Marco,Martinelli, Adriano,Martinotti, Enrica,Orlandini, Elisabetta,Romagnoli, Federico,Rossello, Armando
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p. 911 - 919
(2007/10/03)
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- Inhibitors of protein farnesyltransferase and squalene synthase
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The present invention provides a compound of the formula STR1 or a pharmaceutically acceptable salt thereof, which are useful in inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras or inhibiting de novo squalene production resulting in the inhibition of cholesterol biosynthesis, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.
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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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