- CYCLOALKAPYRROLES FROM KETOXIMES AND ACETYLENE: SYNTHESIS AND KINETIC INVESTIGATION
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The rate constants of formation of cycloalkapyrroles and their N-vinyl derivatives were determined, and it was shown that efficient preparation of pyrroles condensed with aliphatic macrocycles from the corresponding ketoximes and acetylene in the KOH-DMSO system is possible.
- Vasil'tsov, A. M.,Polubentsev, E. A.,Mikhaleva, A. I.,Trofimov, B. A.
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Read Online
- Reduction of the indole ring system: Synthesis of 4,5,6,7-tetrahydroindoles
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A general two-step procedure for the reduction of indoles to the corresponding 4,5,6,7-tetrahydroindoles has been developed. A regioselective Birch reduction followed by catalytic hydrogenation is employed to accomplish this transformation. Yields for the sensitive pyrrole products are typically between 40 and 50%. This method provides access to complex chiral pyrroles that cannot be readily prepared by other methods.
- McComas, Casey C.,Van Vranken, David L.
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Read Online
- A new approach for the synthesis of 2-substituted indole derivatives via Michael type adducts
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4,7-Dihydroindole undergoes regioselective alkylation at the 2-position of the indole nucleus through conjugate addition with α,β-unsaturated carbonyl compounds. The oxidation of the Michael adducts affords the corresponding 2-substituted indole derivatives which were characterized by spectroscopic methods.
- ?avdar, Hüseyin,Sara?o?lu, Nurullah
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Read Online
- Highly efficient one-pot multi-directional selective hydrogenation and N-alkylation catalyzed by Ru/LDH under mild conditions
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Atomic economy, non-toxicity, harmlessness and multidirectional selectivity advocated by green chemistry have increasingly become a hot and difficult research topic. Herein, we present a highly efficient, one-pot tandem and easy-to-operate method through which we could directly produce a broad range of multi-directional selective hydrogenated amines or N-alkyl aliphatic amines using aromatic nitro compounds as raw materials. Ru/LDH with characteristics of layered mesoporous structure, well dispersed small Ru nanoparticles and LDH stabilization to the Ru NPs was employed as the catalyst. It is remarkable that multi-directional superb chemoselectivity to aromatic amines, alicyclic amines as well as N-alkyl aliphatic amines could be achieved with excellent catalytic activity and recyclability by tuning reaction conditions over 5wt%Ru/LDH-2. Additionally, this catalytic system also exhibited attractive activity and multi-directional chemoselectivity in the hydrogenation of quinoline and its derivatives with solvents of different polarity. Chemoselectivity to 5,6,7,8-tetrahydroquinoline derivatives could reach as high as 95.6 %.
- Zhang, Sishi,Xu, Jie,Cheng, Hongmei,Zang, Cuicui,Sun, Bin,Jiang, Heyan,Bian, Fengxia
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supporting information
(2020/03/30)
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- Preparation of cyclic prodiginines by mutasynthesis in pseudomonas putida kt2440
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Prodiginines are a group of naturally occurring pyrrole alkaloids produced by various microorganisms and known for their broad biological activities. The production of nature-inspired cyclic prodiginines was enabled by combining organic synthesis with a mutasynthesis approach based on the GRAS (generally recognized as safe) certified host strain Pseudomonas putida KT2440. The newly prepared prodiginines exerted antimicrobial effects against relevant alternative biotechnological microbial hosts whereas P. putida itself exhibited remarkable tolerance against all tested prodiginines, thus corroborating the bacterium’s exceptional suitability as a mutasynthesis host for the production of these cytotoxic secondary metabolites. Moreover, the produced cyclic prodiginines proved to be autophagy modulators in human breast cancer cells. One promising cyclic prodiginine derivative stood out, being twice as potent as prodigiosin, the most prominent member of the prodiginine family, and its synthetic derivative obatoclax mesylate.
- Klein, Andreas Sebastian,Brass, Hannah Ursula Clara,Klebl, David Paul,Classen, Thomas,Loeschcke, Anita,Drepper, Thomas,Sievers, Sonja,Jaeger, Karl-Erich,Pietruszka, J?rg
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p. 1545 - 1552
(2018/10/21)
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- Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY
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The boron-dipyrromethene (BODIPY) dye containing an annelated cyclohexyl rings at the 2,3 and 5,6-positions of pyrroles has been synthesized and characterized. Photochemical properties of the obtained compound have been investigated in different individua
- Kritskaya, Anna Yu.,Bumagina, Natalia A.,Antina, Elena V.,Ksenofontov, Alexander A.,Berezin, Mikhail B.,Semeikin, Alexander S.
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p. 393 - 407
(2018/01/01)
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- STABILIZATION OF ACTIVE METAL CATALYSTS AT METAL-ORGANIC FRAMEWORK NODES FOR HIGHLY EFFICIENT ORGANIC TRANSFORMATIONS
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Metal-organic framework (MOFs) compositions based on post?synthetic metalation of secondary building unit (SBU) terminal or bridging OH or OH2 groups with metal precursors or other post-synthetic manipulations are described. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations, including the regioselective boryiation and siiylation of benzyiic C—H bonds, the hydrogenation of aikenes, imines, carbonyls, nitroarenes, and heterocycles, hydroboration, hydrophosphination, and cyclization reactions. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.
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Paragraph 0349
(2019/01/07)
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- Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids
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N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1-3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs). Particularly a diol-functionalised IL shows the best performance in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline (1THQ) with up to 99% selectivity.
- Konnerth, Hannelore,Prechtl, Martin H. G.
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supporting information
p. 2762 - 2767
(2017/07/24)
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- Isothiourea-catalysed enantioselective pyrrolizine synthesis: Synthetic and computational studies
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The catalytic enantioselective synthesis of a range of cis-pyrrolizine carboxylate derivatives with outstanding stereocontrol (14 examples, >95:5 dr, >98:2 er) through an isothiourea-catalyzed intramolecular Michael addition-lactonisation and ring-opening
- Stark, Daniel G.,Williamson, Patrick,Gayner, Emma R.,Musolino, Stefania F.,Kerr, Ryan W. F.,Taylor, James E.,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Macgregor, Stuart A.,Smith, Andrew D.
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supporting information
p. 8957 - 8965
(2016/10/07)
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- Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids
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A facile one-pot approach based on a thermally induced metal- and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina- and Lycorine-type alkaloids, namely (±)-erysotramidine, (±)-erysotrine, (±)-erythravine, (±)-γ-lycorane, and abnormal erythrinanes (±)-coccoline and (±)-coccuvinine.
- Andreev, Ivan A.,Ratmanova, Nina K.,Novoselov, Anton M.,Belov, Dmitry S.,Seregina, Irina F.,Kurkin, Alexander V.
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supporting information
p. 7262 - 7267
(2016/05/19)
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- Single-Site Cobalt Catalysts at New Zr8(μ2-O)8(μ2-OH)4 Metal-Organic Framework Nodes for Highly Active Hydrogenation of Alkenes, Imines, Carbonyls, and Heterocycles
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We report here the synthesis of robust and porous metal-organic frameworks (MOFs), M-MTBC (M = Zr or Hf), constructed from the tetrahedral linker methane-tetrakis(p-biphenylcarboxylate) (MTBC) and two types of secondary building units (SBUs): cubic M8(μ2-O)8(μ2-OH)4 and octahedral M6(μ3-O)4(μ3-OH)4. While the M6-SBU is isostructural with the 12-connected octahedral SBUs of UiO-type MOFs, the M8-SBU is composed of eight MIV ions in a cubic fashion linked by eight μ2-oxo and four μ2-OH groups. The metalation of Zr-MTBC SBUs with CoCl2, followed by treatment with NaBEt3H, afforded highly active and reusable solid Zr-MTBC-CoH catalysts for the hydrogenation of alkenes, imines, carbonyls, and heterocycles. Zr-MTBC-CoH was impressively tolerant of a range of functional groups and displayed high activity in the hydrogenation of tri- and tetra-substituted alkenes with TON > 8000 for the hydrogenation of 2,3-dimethyl-2-butene. Our structural and spectroscopic studies show that site isolation of and open environments around the cobalt-hydride catalytic species at Zr8-SBUs are responsible for high catalytic activity in the hydrogenation of a wide range of challenging substrates. MOFs thus provide a novel platform for discovering and studying new single-site base-metal solid catalysts with enormous potential for sustainable chemical synthesis.
- Ji, Pengfei,Manna, Kuntal,Lin, Zekai,Urban, Ania,Greene, Francis X.,Lan, Guangxu,Lin, Wenbin
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supporting information
p. 12234 - 12242
(2016/09/28)
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- Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane
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2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2-4 h), the yields of pyrroles ranging 11-85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions.
- Trofimov, Boris A.,Mikhaleva, Al'Bina I.,Ivanov, Andrei V.,Shcherbakova, Viktoria S.,Ushakov, Igor A.
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p. 124 - 128
(2015/02/02)
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- One-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dibromoethane in the system KOH-DMSO
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Dibutyl ketone, cyclohexanone, acetophenone, α-tetralone, and methyl 2-thienyl ketone were converted into the corresponding 2,3-substituted pyrroles by reaction with hydroxylamine hydrochloride and 1,2-dibromoethane in the system KOH-DMSO.
- Ivanov, A. V.,Shcherbakova, V. S.,Mikhaleva, A. I.,Trofimov, B. A.
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p. 1775 - 1778
(2015/02/05)
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- Ruthenium nanoparticles supported on magnesium oxide: A versatile and recyclable dual-site catalyst for hydrogenation of mono- and poly-cyclic arenes, N-heteroaromatics, and S-heteroaromatics
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The development of catalysts capable of promoting hydrogenation of aromatics while being resistant to poisoning by nitrogen- and sulfur-containing species is of much interest in connection with hydrotreating of fossil fuels. We report a catalyst composed of ruthenium nanoparticles supported on magnesia, designed to promote heterolytic hydrogen splitting and surface ionic hydrogenation pathways. The catalyst, prepared through a one-pot procedure, promotes the hydrogenation of mono- and poly-cyclic arenes, as well as N- and S-heteroaromatics representative of fossil fuels components. Of particular significance are the superior activity and wider substrate scope of the catalyst, in relation to other known supported noble metals, and the excellent recyclability and long catalyst lifetime. Based on our experimental data, a dual-site catalyst structure and an associated dual-pathway mechanism are proposed, which may have interesting implications for the development of new poison-tolerant noble metal catalytic systems.
- Fang, Minfeng,Sanchez-Delgado, Roberto A.
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p. 357 - 368
(2014/02/14)
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- Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles
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A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 °C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole - phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole - phenylacetylene and 2-(2-thienyl)pyrrole - phenylacetylene, respectively).
- Dvorko, Marina Yu.,Schmidt, Elena Yu.,Glotova, Tatyana E.,Shabalin, Dmitrii A.,Ushakov, Igor A.,Kobychev, Vladimir B.,Petrushenko, Konstantin B.,Mikhaleva, Al'Bina I.,Trofimov, Boris A.
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body text
p. 1963 - 1971
(2012/03/22)
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- Hydrogenation of arenes and N-heteroaromatic compounds over ruthenium nanoparticles on poly(4-vinylpyridine): A versatile catalyst operating by a substrate-dependent dual site mechanism
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A nanostructured catalyst composed of Ru nanoparticles immobilized on poly(4-vinylpyridine) (PVPy) has been synthesized by NaBH4 reduction of RuCl3·3H2O in the presence of the polymer in methanol at room temperature. TEM measurements show well-dispersed Ru nanoparticles with an average diameter of 3.1 nm. Both powder XRD patterns and XPS data indicate that the Ru particles are predominantly in the zerovalent state. The new catalyst is efficient for the hydrogenation of a wide variety of aromatic hydrocarbons and N-heteroaromatic compounds representative of components of petroleum-derived fuels. The experimental data indicate the existence of two distinct active sites in the nanostructure that lead to two parallel hydrogenation pathways, one for simple aromatics involving conventional homolytic hydrogen splitting on Ru and a second one for N-heteroaromatics taking place via a novel heterolytic hydrogen activation on the catalyst surface, assisted by the basic pyridine groups of the support.
- Fang, Minfeng,MacHalaba, Nataliya,Sanchez-Delgado, Roberto A.
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experimental part
p. 10621 - 10632
(2011/11/29)
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- COMPOSITIONS AND METHODS FOR TREATMENT OF NEURODEGENERATIVE DISEASE
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Compounds, compositions, kits and methods for treating conditions related to neurodegeneration or ocular disease, are disclosed.
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Page/Page column 35-36
(2011/10/13)
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- The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage
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Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theoretical Gaussian calculations indicate which structural features are likely to lower the enthalpy of dehydrogenation. Experimental results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C-O and C-N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy and 4-amino indoles, and disproportionation during the hydrogenation of 4-aminopyridine. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Cui, Yi,Kwok, Samantha,Bucholtz, Andrew,Davis, Boyd,Whitney, Ralph A.,Jessop, Philip G.
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p. 1027 - 1037
(2008/12/20)
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- Synthesis of 5-substituted 4,5,6,7-tetrahydroindoles from cyclohexanones
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5-Substituted 4,5,6,7-tetrahydroindoles were prepared from 4-substituted cyclohexanones in three steps: conversion to an enol silyl ether, introduction of a formylmethyl group at 2-C, and the Paal-Knorr pyrrole synthesis by reacting the 1,4-dicarbonyl compounds with ammonia. The substituents are H, methyl, ethyl, tert-butyl, methoxy, and phenyl.
- Lee, Chang Kiu,Lee, In-Sook Han,Noland, Wayland
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p. 419 - 428
(2008/02/09)
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- A comparison between silica-immobilized ruthenium(II) single sites and silica-supported ruthenium nanoparticles in the catalytic hydrogenation of model hetero- and polyaromatics contained in raw oil materials
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HDS and HDN are very important hydrotreating reactions that remove sulfur and nitrogen from fossil fuels where they are contained in various organic compounds, which include polyaromatic heterocycles, aliphatic and aromatic thiols and amines, thioethers, disulfides, and nitriles. A comparative study of the hydrogenation of various heterocycles, model compounds in raw oil materials, by either Ru(II) complex immobilized on mesoporous silica or Ru(0) nanoparticles deposited on the same support was conducted. The single-site catalyst contained the molecular precursor [Ru(NCMe)3(sulphos)](OSO2 CF3) tethered to partially dehydroxylated high-surface-area silica through hydrogen bonds between silanol groups of the support and SO3- groups from the sulphos ligand [-O3S(C6H4) CH2C(CH2PPh2)3] and the triflate counter anion. The heterocycles (benzo[b]thiophene, quinoline, indole, acridine) were hydrogenated to cyclic thioethers or amines. Ru(II)-based catalysts were much more efficient for the hydrogenation of S-heterocycles than for N-heterocycles.
- Bianchini, Claudio,Dal Santo, Vladimiro,Meli, Andrea,Moneti, Simonetta,Moreno, Marta,Oberhauser, Werner,Psaro, Rinaldo,Sordelli, Laura,Vizza, Francesco
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- Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(cyclohexylidene)amines
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Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination, (b) α-alkylation with N,N-disilyl-protected ω-bromoamines, (c) transimination, (d) α-chlorination of the resulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenation. Appropriate choice of the reaction conditions selectively led to reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.
- De Kimpe, Norbert,Keppens, Marian
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p. 3705 - 3718
(2007/10/03)
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- Intermediates for making N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase (ACAT)
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Compounds of the formula STR1 wherein R21 and R22 are as defined in the specification which are intermediates useful in the preparation of compounds of the formula STR2 and the pharmaceutically acceptable salts thereof, wherein Q and R1 are as defined in the specification. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.
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- SYNTHESIS OF TRI- AND TETRAMETHYLENEPYRROLE DERIVATIVES FROM 2-(1-ETHOXY-2-BROMOETHYL)CYCLOALKANONES
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Tri- and tetramethylenepyrrole derivatives were synthesized by treatment of the corresponding 2-(1-ethoxy-2-bromoethyl)cycloalkanones with an aqueous solution of sodium hydroxide and a methanol solution of a primary amine.The transformation proceeds th
- Azzuz, A.,Sorokin, V. L.,Kulinkovich, O. G.
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- New N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase
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Compounds of the formula the pharmaceutically acceptable salts thereof, wherein Q and R1 are as defined below, and novel carboxylic acid and acid halide intermediates used in the synthesis of such compounds. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.
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- REACTIONS OF 1-VINYL-4,5,6,7-TETRAHYDROINDOLE AND ITS MIXTURES WITH 4,5,6,7-TETRAHYDROINDOLE IN THE PRESENCE OF Cr- AND Pd-COATED CATALYSTS
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In the presence of Cr- and Pd-coated γ-alumina catalysts. 1-vinyl-4,5,6,7-tetrahydroindole (VTHI) and its mixtures with 4,5,6,7-tetrahydroindole (THI) are converted into 1-ethyl-4,5,6,7-tetrahydroindole (1-ETHI), indole, and 2-ethylindole, in proportions dependent on the reaction conditions and the catalyst.Over a sulfided 1percent Pd-γ-alumina catalyst in the presence of hydrogen at 200 deg C, VTHI is converted into 1-ETHI and THI.When the temperature is raised to 300-350 deg C, indole is formed in addition to these products.A 1:1 mixture of VTHI and THI over 1percent Pd-γ-alumina at 300 deg C gives indole and 2-ethylindole, over a sulfided 1percent Pd-γ-alumina catalyst at 200 deg C, 1-ETHI, and over a Cr oxide catalyst at 500 deg C, indole.
- Ryashentseva, M. A.,Vol'kenshtein, Yu. B.,Polosin, V. M.,Mikhaleva, A. I.,Nesterenko, R. N.
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p. 1257 - 1262
(2007/10/02)
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- Chemo-enzymatic synthesis and characterization of L-tryptophans selectively 13C-enriched or hydroxylated in the six-membered ring using transformed Escherichia coli cells
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L-(3a-13C)- and L-(6-13C)tryptophan have been synthesized from simple labelled compounds via a single reaction scheme based on the conversion of 1,3-cyclohexanedione into indole.The labelled indoles have been converted in one step into the corresponding L-tryptophans using transformed Escherichia coli cells with large amounts of the enzyme, tryptophan synthease.The same reaction scheme has been used for the synthesis of 4- and 7-indolol.These hydroxyindoles together with 5-indolol have been converted into 4-, 7- and 5-hydroxy-L-tryptophan, respectively, using theEscherichia coli cells.The latter compound is the immediate precursor of the neurotransmitter, serotonin.It appears that 7-indolol is the only indole derivative which is converted faster than unsubstituted indole by the enzyme, tryptophan synthease.With the preparation of L-(3a-13C)- and L-(6-13C)tryptophan, we have completed the series of indoles and L-tryptophans with a stable isotope (13C, 15N or 2H) in the aromatic ring.In this paper, we also discuss the NMR parameters of these mono-isotopically labelled systems.
- Berg, E. M. M. van den,Jansen, F. J. H. M.,Goede, A. T. J. W. de,Baldew, A. U.,Lugtenburg, J.
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p. 287 - 297
(2007/10/02)
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- Preparation and Thermal Properties of N-Alkylidene-ethenesulfenamides
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A convenient preparation of N,N-bis(trimethylsilyl)-ethenesulfenamides is described, together with its fluoride-catalysed reaction with aldehydes or ketones to provide several N-alkylidene-ethenesulfenamides.On mild heating, two of these S-vinyl-thio-oximes can converted into the corresponding substituted pyrroles.
- Ruel, Odile,Baudin, Jean-Bernard,Julia, Sylvestre A.
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p. 2151 - 2164
(2007/10/02)
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- Synthesis of Substituted Pyrroles from Ketones
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A number of substituted pyrroles have been prepared through a four step reaction sequence based on the regiospecific alkylation of N,N-dimethylhydrazones with 2-iodomethyl-1,3-dioxolane.
- Chelucci, Giorgio,Marchetti, Mauro
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p. 1135 - 1137
(2007/10/02)
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- A Synthesis of Pyrrole Derivatives from O-(2-Hydroxyethyl)-ketoximes
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Acetophenone, cyclohexanone, cycloheptanone, cyclo-octanone, and heptan-4-one were converted, via their O-(2-hydroxyethyl)-oximes into the pyrrole derivatives in satisfactory overall yields.
- Dhanak, Dashyant,Reese, Colin B.,Romana, Sergio,Zappia, Giovanni
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p. 903 - 904
(2007/10/02)
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- PYRROLES FROM KETOXIMES AND ACETYLENE. CONDITIONS OF REACTION OF CYCLOHEXANONE OXIME WITH VINYL HALIDES IN SUPERBASIC MEDIA
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4,5,6,7-Tetrahydroindole and its N-vinyl derivatives were synthesized with an overall yield of up to 60percent by the reaction of cyclohexanone oxime with vinyl halides (CH2=CHX, where X = Cl, Br) in a MOH (M = Na, K)-polar aprotic solvent system at 84-140 deg C and atmospheric pressure.
- Aliev, I. A.,Mikhaleva, A. I.,Bairamova, S. Kh.,Akhmedov, E. I.
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p. 433 - 435
(2007/10/02)
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- Synthesis of Alkylpyrroles by the Sodium Borohydride Reduction of Acylpyrroles
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N-Unsubstituted alkylpyrroles are obtained by the reduction of the corresponding acylpyrroles with sodium borohydride in boiling 2-propanol.This reaction was demonstrated to proceed via the pyrrolylalkylcarbinol and was extended to the synthesis of a branched chain alkylpyrrole 25 from the tertiary alcohol 24.
- Greenhouse, Robert,Ramirez, Coral,Muchowski, Joseph M.
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p. 2961 - 2965
(2007/10/02)
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- PYRROLES FROM KETOXIMES AND ACETYLENE. 22. DIHALOETHANES IN PLACE OF ACETYLENE IN REACTIONS WITH CYCLOHEXANONE OXIME
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4,5,6,7-Tetrahydroindole and its 1-vinyl derivative were obtained in overall yields of 30-60percent by the reaction of cyclohexanone oxime with 1,2-dichloro- and 1,2-dibromoethane in the MOH-dimethyl sulfoxide (DMSO) superbase system (M = K, Na, Li).Nucle
- Mikhaleva, A. I.,Trofimov, B. A.,Vasil'ev, A. N.,Komarova, G. A.,Skorobogatova, V. I.
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p. 920 - 923
(2007/10/02)
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- PYRROLES FROM KETOXIMES AND ACETYLENE. 24. ACIDIC HYDROLYSIS OF 1-VINYLPYRROLES
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The hydrolysis of 2-methyl-, 2-phenyl-, and 3-methyl-2-phenyl-1-vinylpyrroles and 1-vinyl-4,5,6,7-tetrahydroindole in the presence of HCl, H2SO4, NH2OH*HCl, acetic acid, and H2O2 in aqueous, aqueous dioxane, and aqueous alcohol solutions leads to oligomers with complex structures and compositions, viz., products of acidic catalytic and oxidative condensation of the starting compounds and the resulting pyrroles both with one another and with the liberated acetaldehyde. 2-Phenylpyrrole was obtained in 52percent yield from 1-vinyl-2-phenylpyrrole by hydrolysis in a dilute (0.5percent) solution with excess NH2OH*HCl, which ties up the acetaldehyde.
- Trofimov, B.A.,Korostova, S.E.,Mikhaleva, A.I.,Sobenina, L.N.,Vasil'ev, A.N.
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p. 1257 - 1265
(2007/10/02)
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- PYRROLES FROM KETOXIMES AND ACETYLENE XVII. STUDY OF THE CONDITIONS FOR THE REACTION OF CYCLOHEXANONE OXIME WITH ACETYLENE IN SUPERBASIC MEDIA
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The principal trends in the effects of the solvent and the concentration and nature of the hydroxide (MOH, M = Li, Na, K, Rb, Cs, Bu4N) on the yield and ratio of 4,5,6,7-tetrahydroindole and its 1-vinyl derivative, obtained from cyclohexanone oxime and acetylene in a single stage were investigated.
- Mikhaleva, A. I.,Vasil'ev, A. N.,Trofimov, B. A.
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p. 1763 - 1766
(2007/10/02)
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