19686-05-6Relevant academic research and scientific papers
Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds
Abe, Takumi,Shimizu, Haruka,Takada, Shiori,Tanaka, Takahiro,Yoshikawa, Mai,Yamada, Koji
, p. 1589 - 1592 (2018)
A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.
1,2,3,4-Tetrahydro-γ-carbolinium salts: Novel reactions with thiols, mediated by polymer-supported reagents
Lizarzaburu, Mike E.,Shuttleworth, Stephen J.
, p. 4781 - 4783 (2004)
A series of dialkyl-[2-(3-alkylsulfanylmethyl-1H-indol-2-yl)-ethyl]amines was produced using a novel route involving nucleophilic ring opening of 2,2-dialkyl-1,2,3,4-tetrahydro-γ-carbolinium salts with thiols. The insertion reaction was mediated by a strong, polymer-supported base, and the purification of the target compounds was facilitated using resin-bound sulfonic acid.
Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst
Misal Castro, Luis C.,Sultan, Ibrahim,Nishi, Kohei,Tsurugi, Hayato,Mashima, Kazushi
, p. 3287 - 3299 (2021/03/01)
Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.
Careful investigation of the hydrosilylation of olefins at poly(ethylene glycol) chain ends and development of a new silyl hydride to avoid side reactions
Shin, Hyunseo,Moon, Bongjin
, p. 527 - 536 (2018/01/27)
Hydrosilylation of olefin groups at poly(ethylene glycol) chain ends catalyzed by Karstedt catalyst often results in undesired side reactions such as olefin isomerization, hydrogenation, and dehydrosilylation. Since unwanted polymers obtained by side reactions deteriorate the quality of end-functional polymers, maximizing the hydrosilylation efficiency at polymer chain ends becomes crucial. After careful investigation of the factors that govern side reactions under various conditions, it was related that the short lifetime of the unstable Pt catalyst intermediate led to the formation of more side products under the inherently dilute conditions for polymers. Based on these results, two new chelating hydrosilylation reagents, tris(2-methoxyethoxy)silane (5) and 2,10-dimethyl-3,6,9-trioxa-2,10-disilaundecane (6), have been developed. It was demonstrated that the hydrosilylation efficiency at polymer chain ends was significantly increased by employing the internally coordinating hydrosilane 5. In addition, employment of the internally coordinating disilane species 6 in an addition polymerization with 1,5-hexadiene by hydrosilylation reaction yielded a polymer with high molecular weight (Mn = 9300 g/mol), which was significantly higher than that (Mn = 2600 g/mol) of the corresponding polymer obtained with non-chelating dihydrosilane, 1,1,3,3-tetramethyldisiloxane.
Anion Receptor, Electrolyte Containing the Anion Receptor and Lithium Ion Battery and Lithium Ion Capacitor Using the Electrolyte
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Paragraph 0088-0090, (2018/09/30)
The present invention relates to a novel anion acceptor having a high cation transport rate and improved lifespan, an electrolyte containing the same, and a lithium ion battery and a lithium ion capacitor manufactured using the electrolyte and, more specifically, to a compound represented by chemical formula 1. In the chemical formula 1, n is an integer from 1 to 50, and X is one or more selected from the group consisting of -NR_1R_2, -NR_3R_4, -Ph(-(m)-R_5), and -O-(CH_2CH_2O)_y-CH_3.COPYRIGHT KIPO 2018
Plasticizing Li single-ion conductors with low-volatility siloxane copolymers and oligomers containing ethylene oxide and cyclic carbonates
Liang, Siwei,Chen, Quan,Choi, U Hyeok,Bartels, Joshua,Bao, Nanqi,Runt, James,Colby, Ralph H.
, p. 21269 - 21276 (2015/11/09)
To prepare a safe electrolyte for lithium ion batteries, two groups of novel low-volatility plasticizers combining pendant cyclic carbonates and short ethylene oxide chains have been successfully synthesized, as confirmed by 1H, 13C and 29Si NMR spectroscopy. The Fox equation describes the composition dependence of the glass transition temperature (Tg) very well for the random polysiloxane-based copolymer plasticizers (11000 g as much as 20 K lower than the Fox equation prediction because of their lower molecular weight (450 g. Mixing with 20 wt% polysiloxane tetraphenyl borate-Li ionomer (14 mol% borate and 86 mol% cyclic carbonate) increases conductivity relative to the neat ionomer by lowering Tg, increasing dielectric constant and providing better solvation of Li+. The best oligomeric plasticizer only has Tg 10 K lower than the Fox prediction but has dielectric constant 30% larger than expected by the Landau-Lifshitz mixing rule, owing to a surprisingly low viscosity, resulting in ambient conductivity 2 × 10-5 S cm-1. For both groups of plasticizers, the fraction of cyclic carbonates relative to ethylene oxide governs the magnitude and temperature dependence of the ionic conductivity.
Thermodynamic Properties of Carbosilane Dendrimers of the Sixth Generation with Ethylene Oxide Terminal Groups
Sologubov, Semen S.,Markin, Alexey V.,Smirnova, Natalia N.,Novozhilova, Natalia A.,Tatarinova, Elena A.,Muzafarov, Aziz M.
, p. 14527 - 14535 (2015/11/23)
The temperature dependences of heat capacities of carbosilane dendrimers of the sixth generation with ethyleneoxide terminal groups, denoted as G6[(OCH2CH2)1OCH3]256 and G6[(OCH2CH2)3OCH3]256, were measured in the temperature range from T = (6 to 520) K by precision adiabatic calorimetry and differential scanning calorimetry (DSC). In the above temperature range the physical transformations, such as glass transition and high-temperature relaxation transition, were detected. The standard thermodynamic characteristics of the revealed transformations were determined and analyzed. The standard thermodynamic functions, namely, heat capacity Cp°(T), enthalpy H°(T) - H°(0), entropy S°(T) - S°(0), and Gibbs energy G°(T) - H°(0) for the range from T → 0 to 520 K, and the standard entropies of formation ΔfS°of the investigated dendrimers in the devitrified state at T = 298.15 K, were calculated per corresponding moles of the notional structural units. The standard thermodynamic properties of dendrimers under study were discussed and compared with literature data for carbosilane dendrimers with different functional terminal groups.
Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use
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Page/Page column 182; 183, (2016/03/05)
This disclosure is directed to pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder. The compounds may bind to and antagonize receptor α2B, α1B or α2A. The compounds may find use in therapy, e.g., to (i) reduce blood pressure and/or (ii) promote renal blood flow and/or (iii) decrease or inhibit sodium reabsorption, or to regulate blood glucose level, increase insulin secretion and treat diseases or conditions that are, or are expected to be, responsive to an increase in insulin production. The compounds may also be used to treat diseases or conditions that are expected to be responsive to a decrease in blood pressure. Use of the compounds to treat cardiovascular, renal disorders or type 2 diabetes is particularly described.
New route of benzyne cyclization for synthesis of 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole derivatives avoiding highly toxic aryl hydrazines
Kovacikova, Lucia,Stefek, Milan
, p. 1257 - 1263 (2015/04/27)
A new route for the regioselective synthesis of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole derivatives was developed based on cyclization of 3-chlorophenylimine-N-alkyl-4-piperidones by "the complex bases" of NaNH2 or KNH2. The procedure was performed under variable reaction conditions in inert proton-free solvents, such as THF, dioxane, 1,2-dimethoxyethane, toluene, and xylene, at temperatures varying from 20C to boiling point of the solvent used. Toxic arylhydrazine intermediates occurring in the classical Fischer indole synthesis are avoided.
High ion content siloxane phosphonium ionomers with very low T g
Liang, Siwei,Oreilly, Michael V.,Choi, U Hyeok,Shiau, Huai-Suen,Bartels, Joshua,Chen, Quan,Runt, James,Winey, Karen I.,Colby, Ralph H.
, p. 4428 - 4437 (2014/07/22)
Polysiloxane phosphonium single-ion conductors grafted with oligomeric PEO and with ion contents ranging from 5 to 22 mol % were synthesized via hydrosilylation reaction. The parent Br- anion was exchanged to F- or bis(trifluoromethanesulfonyl)imide (TFSI-). X-ray scattering data suggest ion aggregation is absent in these phosphonium ionomers, which contributes to low glass transition temperatures (below -70 °C) with only a weak dependence on both ion content and counteranion type. Conductivities weakly increase with ion content but exhibit a strong dependence on anion type. The highest conductivity at 30 °C is 20 μS/cm for dry neat ionomer, with the TFSI- anion, consistent with its relatively delocalized negative charge and large size that weaken interactions between TFSI- and the phosphonium cation.
