- Generation of cyclopenta[c]piperidines and pyrrolo[3,4-c]piperidines-Potential substance P antagonists - From adducts of cyclic dienophiles and 5-chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one
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1,1,4,4-Tetrasubstituted cyclopenta[c]piperidines and the corresponding 4,4,7,7-pyrrolo[3,4-c]piperidines have been synthesised via cycloaddition of 5-chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one with cyclopentene and 3-pyrroline derivatives, respectively, followed by reductive opening of the lactone-bridged adducts. The axial-equatorial conformational preferences of the substituents in these cis-fused bicyclic systems were opposite to those for the monocyclic piperidine analogues. The specific array of functional groups in the bicyclic aminoalcohols was used to accommodate, in stereocontrolled fashion, variable pharmacophoric groups that are of interest for substance P antagonist activity. (C) 2000 Elsevier Science Ltd.
- Wu, Xiujuan,Toppet, Suzanne,Compernolle, Frans,Hoornaert, Georges J.
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- Catalytic ring-closing olefin metathesis of sulfur-containing species: Heteroatom and other effects
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This paper describes studies of the ring-closing metathesis of dialkyl sulfides and disulfides catalyzed by molybdenum and ruthenium alkylidenes. In general, the highest yields of ring-closed products were obtained using the molybdenum catalysts. Product yields were also strongly influenced by the substitution pattern about the double bonds: the yield of ring-closed products was found to decrease as the degree of substitution increased. These effects and other heteroatom effects are discussed.
- Shon, Young-Seok,Lee, T. Randall
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- Unsaturated 1,2-amino alcohols from dihydropyrrole epoxides and organolithiums
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The alkylative double ring-opening of Bus-protected 2,5-dihydropyrrole epoxide 11 with organolithiums to give 3-substituted 1-aminobut-3-en-2-ols 13-19 is described.
- Hodgson, David M.,Miles, Timothy J.,Witherington, Jason
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- RELATIVE STABILITIES OF 5-MEMBERED CYCLIC ALLYLAMINE/ENAMINE SYSTEMS
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Evidence bearing on the relative stabilities of 3- and 2-pyrrolines is reviewed.It is shown that 1-(indol-3-ylethyl)-3-pyrroline is only partially transformed into its enamine isomer by prolonged base treatment and it is concluded that within a 5-membered ring the allylamine is more stable than enamine.
- Ashcroft, William R.,Martinez, Silvio J.,Joule, John, A.
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- Method for preparing 3-pyrroline based on improved activated zinc powder
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The invention discloses a method for preparing 3-pyrroline based on improved activated zinc powder, and belongs to the technical field of medicines, wherein dimethyl sulfoxide is used as a solvent, aromatic carboxylic acid is used for activating zinc powder, active zinc powder is obtained after filtering, the active zinc powder reacts with hydrochloric acid to generate reactive hydrogen, and the reactive hydrogen is used for selectively hydrogenating pyrrole to generate 3-pyrroline. According to the invention, aromatic carboxylic acid used in the invention not only can remove zinc oxide on the surface of the zinc powder, but also can form a coordination compound with a spatial network structure with zinc, so that the safety of the activated zinc powder is enhanced, and the reaction activity of the zinc powder and the selectivity of a pyrrole selective hydrogenation reaction are effectively improved; through the dispersion effect of dimethyl sulfoxide on the zinc powder, the activation effect of the zinc powder is enhanced; and dimethyl sulfoxide complexed on the surface of active zinc in the process of selective hydrogenation of pyrrole can effectively capture hydrogen ions and transmit the hydrogen ions to zinc powder, so that the generation of reactive hydrogen is promoted, and the conversion rate of the reaction is improved.
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Paragraph 0035-0059
(2021/09/04)
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- CRYSTAL AND SALT OF NITROIMIDAZOLE, AND MANUFACTURING METHOD THEREOF
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The present invention discloses a crystal form and salt of a nitroimidazole compound, and a manufacturing method thereof. The invention further comprises an application of the crystal form and salt in preparing a pharmaceutical product for preventing and treating an infection caused by Mycobacterium tuberculosis or another microbe.
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Paragraph 0087-0089
(2019/09/20)
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- Sequential reactions with Grubbs catalyst and ad-mix-α//βusing pdms thimbles
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Incompatible Grubbs catalyst and an osmium dihydroxylation catalyst were site-isolated from each other using polydimethylsiloxane thimbles. The Grubbs catalyst was added to the interior of the thimbles, and AD-mix-α//β was added to the exterior. Organic substrates readily fluxed through the walls of the thimbles and reacted with each catalyst. A series of cascade reactions were developed including those with intermediates possessing low boiling points or that were foul smelling.
- Mwangi, Martin T.,Schulz, Michael D.,Bowden, Ned B.
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supporting information; experimental part
p. 33 - 36
(2009/08/08)
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- Practical one-pot and large-scale synthesis of N-(tert-butyloxycarbonyl)-3- pyrroline
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N-(tert-Butyloxycarbonyl)-3-pyrroline was prepared with high purity in large scale starting from cis-1,4-dichloro-2-butene via delepine reaction and subsequent cyclization in the presence of potassium carbonate followed by N-Boc protection in methanol.Judicious selection of base and solvent led to the use of a single solvent, i.e., methanol, for cyclization as well as for N-Boc protection to render the one-pot process from compound 2 more practical and greener than the stepwise version.
- Rajesh, Tammana,Azeez, Shaik Abdul,Naresh, Erragunta,Madhusudhan, Gutta,Mukkanti, Kagga
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experimental part
p. 638 - 640
(2010/04/22)
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- Heterocyclic lithium amides as chiral ligands for an enantioselective hydroxyalkylation with n-BuLi
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(Chemical Equation Presented) Chiral heterocyclic structures based on 3-aminopyrrolidines (3APs), 3-aminotetrahydrothiophens (3ATTs), and 3-aminotetrahydrofurans (3ATFs) have been synthesized. The corresponding lithium amides have been evaluated as chiral ligands in the condensation of n-BuLi on o-tolualdehyde. The returned levels of induction were in the 46-80% ee range. The cheap and easily prepared 3ATFLi's turned out to be also the best ligands, giving access to the expected R or S alcohols in a same 80% level of induction at -78°C in THF. In all cases, the sense of induction depends on the absolute configuration of C8 on the 3-amino appendage. A general concept is proposed to rationalize the process of induction in the presence of organolithium species.
- Duguet, Nicolas,Petit, Sylvain M.,Marchand, Philippe,Harrison-Marchand, Anne,Maddaluno, Jacques
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p. 5397 - 5409
(2008/12/21)
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- RUTHENIUM COMPOUNDS, THEIR PRODUCTION AND USE
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A new class of compounds is disclosed that in preferred embodiments relate to Ru-based catalysts suitable for use in olefin metathesis reactions. Such compounds demonstrate high rates of catalytic turnover in comparison with other Ru catalysts known in the art. Moreover, the catalysts are highly stable, and readily suited to attachment to a solid support via the anionic ligands. In preferred embodiments the compounds present significant advantages by permitting facile isolation of active catalyst. The invention also pertains to methods of producing the catalysts, and their use in catalyzing olefin metathesis reactions.
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Page/Page column 35-36; 38
(2008/06/13)
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- Organolithium-induced synthesis of acyclic unsaturated amino alcohols from epoxides of dihydropyrroles and tetrahydropyridines
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The alkylative double ring-opening of Bus-protected 2,5-dihydropyrrole epoxides 13 and 29 with organolithiums to give 3-substituted 1-aminobut-3-en-2-ols 13-19 and 30-32 are described. Bus-protected tetrahydropyridine epoxide 38 reacts with organolithiums to give 4-substituted 1-aminobut-4-en-3-ols 39 and tetrahydropyridinol 40.
- Hodgson, David M.,Miles, Timothy J.,Witherington, Jason
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p. 9729 - 9742
(2007/10/03)
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- 14-substituted marcfortines and derivatives useful as antiparasitic agents
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There are disclosed 14α-hydroxymarcfortine derivatives of the natural products marcfortine A, B, C, and D useful in the treatment and prevention of helminth and arthropod infections of animals and plants. The synthetic derivatives are of Formula (I). STR1
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- Marcfortine/paraherquamide derivatives useful as antiparasitic agents
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There are disclosed 18-thiomarcfortine derivatives of the natural products marcfortine A, B and C, C-18 thioparaherquamide and derivatives thereof, novel N-1 marcfortines A, B, and C and derivatives thereof, novel N-1 paraherquamide and derivatives thereof usefull in the treatment and prevention of helninth and arthropod infections of animals and plants. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Examiner Robert T. Bond whose telephone number is (703)308-4711. The examiner can normally be reached on Monday through Friday from 8:00 AM to 4:30 PM.
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- Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
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This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones
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This invention relates to compounds of Formula I STR1 which are useful in association with a pharmaceutical carrier as antiatherosclerotic agents. In addition, various compounds of Formula I are useful inhibitors of cell proliferation.
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- Rutheniumkatalysierte Metathese polymergebundener Olefine
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Keywords: Festphasensynthesen; Heterocyclen; Katalysen; Metathese; Rutheniumverbindungen
- Schuster, Matthias,Pernerstorfer, Josef,Blechert, Siegfried
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p. 2111 - 2112
(2007/10/03)
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- Antiatherosclerotic and antithrombotic 2-amino-6-phenyl-4H-pyran-4-ones
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This invention relates to compounds of Formula I STR1 which are useful as antiatherosclerotic agents and inhibitors of cell proliferation for the treatment of proliferative diseases. In addition, various compounds of Formula I are useful inhibitors of platelet aggregation.
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- A Convenient Route to 3-Pyrroline Utilizing the Delepine Reaction
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3-Pyrroline(2,5-dihydro-1H-pyrrole) has been prepared from (Z)-1,4-dichloro-2-butene (1) in three steps in an overall yield of 74percent.
- Brandaenge, Svante,Rodriguez, Benito
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p. 347 - 348
(2007/10/02)
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- A NEW SYNTHESIS OF AROMATIC AND HETEROAROMATIC NITROGEN MUSTARDS VIA 3-PYRROLINES
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Reaction of aromatic and heteroaromatic halides with 3-pyrroline gives adducts which can be converted in a three-step process to nitrogen mustards.
- Palmer, Brian D,Denny, William A
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p. 601 - 610
(2007/10/02)
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- Treatment of atherosclerosis with khellin-related furochromones
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The present specification relates to the antiatherosclerotic use of khellin and related furochromones, and further provides novel antiatherogenic furochromones.
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- DEACYLATION OF ALKYL CARBAMATES: SELECTIVE DEPROTECTION OF SECONDARY AMINES
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Selective deacylation of N,N-disubstituted alkyl carbamates over N-monosubstituted alkyl carbamates can be acheived in excellent yield by the addition of three equivalents of methyl lithium.
- Sawyer, J. Scott,Narayanan, Bikshandarkoil A.
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p. 135 - 138
(2007/10/02)
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- Antiatherosclerotic furochromones
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The present specification relates to the antiatherosclerotic use of khellin and related furochromones, and further provides novel antiatherogenic furochromones.
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