- CARBAMATE DERIVATIVES AND USES THEREOF
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The present disclosure relates to compounds of Formula (I): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.
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Paragraph 01371
(2020/08/13)
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- Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover
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A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.
- Phelan, James P.,Lang, Simon B.,Compton, Jordan S.,Kelly, Christopher B.,Dykstra, Ryan,Gutierrez, Osvaldo,Molander, Gary A.
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supporting information
p. 8037 - 8047
(2018/07/03)
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- Palladium-Catalyzed Carbonylative Cross-Coupling Reaction between Aryl(Heteroaryl) Iodides and Tricyclopropylbismuth: Expedient Access to Aryl Cyclopropylketones
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The carbonylative cross-coupling reaction between aryl and heteroaryl iodides and tricyclopropylbismuth is reported. The reaction is catalyzed by (SIPr)Pd(allyl)Cl, a NHC-palladium(II) catalyst, operates under 1 atm of carbon monoxide and tolerates a wide range of functional groups. The use of lithium chloride was found to provide higher yields of the desired aryl cyclopropylketones. The conditions were also applied to the carbonylative cross-coupling of an iodoalkene to afford the corresponding alkenyl cyclopropylketone.
- Benoit, Emeline,Dansereau, Julien,Gagnon, Alexandre
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supporting information
p. 2833 - 2838
(2017/10/06)
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- Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate
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We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions-two photochemical, two purely chemical-generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated provided valuable clues that led to the proposal of a "unifying" chain propagation mechanism beyond initiation, tied by a common intermediate. In all, the proposed mechanism herein is substantiated by product distribution studies, kinetic analyses, LFERs, Rehm-Weller estimations of ΔGET, competition experiments, KIEs, fluorescence data, and DFT calculations. From a more physical standpoint, transient-absorption experiments have allowed direct spectroscopic observation of radical ion intermediates (previously only postulated or probed indirectly in photochemical fluorination systems) and, consequently, have provided kinetic support for chain propagation. Lastly, calculations suggest that solvent may play an important role in the cyclopropane ring-opening step.
- Pitts, Cody Ross,Ling, Bill,Snyder, Joshua A.,Bragg, Arthur E.,Lectka, Thomas
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supporting information
p. 6598 - 6609
(2016/06/09)
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- OXADIAZINE COMPOUNDS AND METHODS OF USE THEREOF
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The present disclosure relates to oxadiazine compounds, pharmaceutical compositions comprising an effective amount of an oxadiazine compound and methods for using an oxadiazine compound in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of an oxadiazine compound.
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Paragraph 0662
(2016/12/26)
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- SUBSTITUTED PYRIMIDINE COMPOUNDS AS mPGES-1 INHIBITORS
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The present disclosure is directed to substituted pyrimidine compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and a
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Page/Page column 42
(2015/05/06)
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- Facile synthesis of aryl(het)cyclopropane catalyzed by palladacycle
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Sphos (2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′- biphenyl) adduct of cyclopalladated ferrocenylimine (IIe) exhibited highly catalytic activity for the Suzuki cross-coupling reaction of cyclopropylboronic acid with aryl(het) halides with 1 mol % catalyst loading. This process was applied to both of aryl and heteroaryl halides (Br and Cl), and made the various arylcyclopropane and heteroarylcyclopropane to be easily synthesized. A variety of substituents on the aryl halides, such as alkyl, acetyl, benzoyl, ether, formyl, carboxylate, methoxy, nitro and cyano were tolerated.
- Zhang, Min,Cui, Xiuling,Chen, Xiaopei,Wang, Lianhui,Li, Jingya,Wu, Yusheng,Hou, Lifen,Wu, Yangjie
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experimental part
p. 900 - 905
(2012/02/01)
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- CYCLOPROPYL- AND CYCLOBUTYL-DIOXAZABOROCANE OR DIOXAZABORECANE DERIVATIVES
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The present invention relates to borated cyclopropyl or cyclobutyl derivatives of formula (I) and to a process for their preparation in which the groups R1 and R2, n, m are as defined in claim 1. The derivatives can be used in particular for storing the corresponding boronic acid derivatives or as precursors of the boronic acid derivatives in Suzuki coupling reactions especially.
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Page/Page column 14; 16
(2010/04/03)
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- SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS
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A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.
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Page/Page column 65-66, 73
(2010/04/27)
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- General and user-friendly protocol for the synthesis of functionalized aryl- and heteroaryl-cyclopropanes by Negishi cross-coupling reactions
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The introduction of an unsubstituted cyclopropyl moiety was efficiently accomplished via Negishi cross-coupling of cyclopropylzinc bromide with functionalized aryl halides in high yields and fast reaction rates. The stability and the efficient one-step sy
- Coleridge, Brian M.,Bello, Charles S.,Leitner, Andreas
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experimental part
p. 4475 - 4477
(2009/12/03)
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- Phenyl bridging in ring-substituted cumyloxyl radicals. a product and time-resolved kinetic study
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The reactivity of cumyloxyl radicals bearing cyclopropyl and 2,2-diphenylcyclopropyl groups in the para position has been investigated. Depending on radical structure, products deriving from C-C β-scission and/or cyclopropyl ring-opening are observed, sup
- Salamone, Michela,Bietti, Massimo,Calcagni, Alessandra,Gente, Giacomo
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supporting information; experimental part
p. 2453 - 2456
(2009/10/24)
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- Chemical and biological investigation of cyclopropyl containing diaryl-pyrazole-3-carboxamides as novel and potent cannabinoid type 1 receptor antagonists
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Obesity is a major clinical problem in the western world, and many molecular targets have been explored in the search for effective therapeutic agents. One of these, antagonism of the cannabinoid 1 (CB1) receptor, rose to prominence following reports demo
- Szabó, Gyorgy,Varga, Balázs,Páyer-Lengyel, Dóra,Szemzo, Attila,Erdélyi, Péter,Vukics, Krisztina,Szikra, Judit,Hegyi, éva,Vastag, Mónika,Kiss, Béla,Laszy, Judit,Gyertyán, István,Fischer, János
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supporting information; experimental part
p. 4329 - 4337
(2010/02/28)
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- Palladium-catalyzed cross-coupling reaction of tricyclopropylbismuth with aryl halides and triflates
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(Chemical Equation Presented) The palladium-catalyzed cross-coupling reaction of tricyclopropylbismuth with aryl and heterocyclic halides and triflates is reported. The reaction tolerates numerous functional groups and does not require anhydrous conditions. The method was successfully extended to the cross-coupling of triethylbismuth.
- Gagnon, Alexandre,Duplessis, Martin,Alsabeh, Pamela,Barabe, Francis
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p. 3604 - 3607
(2008/09/20)
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- Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium-tetraphosphine complex
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The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)- cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords a very efficient catalyst for the coupling of cyclopropylboronic acid with aryl bromides and aryl chlorides. Higher reactions rates were observed with aryl bromides than with aryl chlorides; however, even in the presence of 1-0.4% of catalyst, a few aryl chlorides gave the coupling products in good yields. A wide variety of substituents such as alkyl, methoxy, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, and nitrile on the aryl halides are tolerated. The coupling reaction of sterically very congested aryl bromides such as bromomesitylene or 2,4,6-triisopropylbromobenzene also proceeds in good yields. Copyright Taylor & Francis LLC.
- Lemhadri, Mhamed,Doucet, Henri,Santelli, Maurice
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p. 121 - 128
(2007/10/03)
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- Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles
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The novel metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles is described. Triorganoindium compounds (R3In) containing alkyl, vinyl, aryl, and alkynyl groups are efficiently prepared from the correspond
- Perez,Sestelo,Sarandeses
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p. 4155 - 4160
(2007/10/03)
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- Palladium-catalyzed cross-coupling reactions of triorganoindium compounds with vinyl and aryl triflates or iodides
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(matrix presented) A novel palladium-catalyzed cross-coupling reaction of organoindium compounds with vinyl and aryl triflates or iodides is described. The reaction proceeds for alkyl-, vinyl-, alkynyl-, and arylindium compounds in excellent yields and high chemoselectivity without any excess of the organometallic. Remarkably, indium organometallics transfer efficiently the three organic groups attached to the metal.
- Perez, Ignacio,Sestelo, Jose Perez,Sarandeses, Luis A.
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p. 1267 - 1269
(2008/02/09)
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- Synthesis of Certain Mesogenic Azomethines Derived from 4-Cycloalkylanilines and from 4-Cycloalkylbenzaldehydes
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General procedures are described for the synthesis of members of five pairs of related homologous series of mesogenic azomethines differing in the mode of linkage of the CH=N group and containing a cycloalkyl group in a terminal position.
- Byron, D. J.,Matharu, A. S.,Rees, M.,Wilson, R. C.
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p. 229 - 238
(2007/10/02)
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