- Addition Reaction of Immonium Benzotriazolates To Acetylenic Esters
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1-Dialkylaminomethylbenzotriazoles react with ethyl propiolate and dimethyl acetylenedicarboxylate by addition of the benzotriazole anion followed by the immonium cation.The benzotriazolyl group in the products undergoes facile nucleophilic displacement.
- Katritzky, Alan R.,Fali, Clara N.,Oniciu, Daniela C.
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- Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks
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Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.
- Dos Santos, Maurício Silva,Ferreira, Byanca Silva,Silva, Rafaela Corrêa,Souto, Bernardo Araújo
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p. 335 - 343
(2021/09/07)
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- Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants
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We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.
- Targos, Karina,Williams, Oliver P.,Wickens, Zachary K.
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p. 4125 - 4132
(2021/04/07)
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- NOVEL COMPOUND AS MTOR INHIBITOR AND USE THEREOF
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The present invention relates to a novel compound as an mTOR inhibitor and a use thereof and, more specifically, to a novel compound represented by formula 1 that exhibits mTOR inhibitory activity and a pharmaceutical composition comprising same as an act
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Paragraph 0063; 0096
(2021/03/04)
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- Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
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Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.
- Huang, He,Strater, Zack M.,Rauch, Michael,Shee, James,Sisto, Thomas J.,Nuckolls, Colin,Lambert, Tristan H.
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supporting information
p. 13318 - 13322
(2019/08/12)
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- L -(-) -Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles
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l-(-)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.
- Zhou, Qifan,Du, Fangyu,Chen, Yuanguang,Fu, Yang,Sun, Wenjiao,Wu, Ying,Chen, Guoliang
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p. 8160 - 8167
(2019/06/28)
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- Copper-catalyzed C–N cross-coupling of arylboronic acids with N-acylpyrazoles
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A copper-catalyzed C–N bond forming reaction of arylboronic acids and N-acylpyrazoles was developed. This procedure used N-acetyl protected pyrazoles as starting material instead of free pyrazoles (NH). The reaction worked under neutral conditions and did not require any base or ligand. The reaction showed good functional group tolerance.
- Zhang, Jin,Jia, Run-Ping,Wang, Dong-Hui
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supporting information
p. 3604 - 3607
(2016/07/21)
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- Cu-promoted sydnone cycloadditions of alkynes: Scope and mechanism studies
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Cu salts have been found to promote the cycloaddition reaction of sydnones and terminal alkynes, providing significant reduction in reaction times. Specifically, the use of Cu(OTf)2 is found to provide 1,3-disubstituted pyrazoles, whereas simpl
- Comas-Barcel?3, Jffllia,Foster, Robert S.,Fiser, B??la,Gomez-Bengoa, Enrique,Harrity, Joseph P. A.
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supporting information
p. 3257 - 3263
(2015/03/05)
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- nBu3P-catalyzed desulfonylative [3 + 2] cycloadditions of allylic carbonates with arylazosulfones to pyrazole derivatives
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Highly efficient nBu3P-catalyzed desulfonylative [3 + 2] cycloadditions of allylic carbonates with arylazosulfones were developed for the synthesis of pyrazole derivatives. The reactions proceed smoothly under mild conditions to gene
- Zhang, Qi,Meng, Ling-Guo,Wang, Kuai,Wang, Lei
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supporting information
p. 872 - 875
(2015/04/21)
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- One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction
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A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.
- Specklin, Simon,Decuypere, Elodie,Plougastel, Lucie,Aliani, Soifia,Taran, Frédéric
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p. 7772 - 7777
(2014/10/15)
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- Phosphinodefluorination of polyfluorobenzenes by silylphosphines Ph(R)PSiMe3 (R = Me, Ph): Further experimental and computational evidences for the concerted ANDN mechanism of aromatic nucleophilic substitution
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Trimethylsilylphosphines PhRPSiMe3 (1 R = Me, 2 R = Ph) have been shown to phosphinodefluorinate 1,2,3- (3), 1,3,5- (4) and 1,2,4-trifluorobenzene (5) in benzene solution or without solvent at 150-200 °C to form the respective (difluorophenyl)methylphenyl- and -diphenylphosphines in high NMR yields under harder conditions compared to the previously reported reactions of Me2PSiMe3 with the same substrates. Hexafluorobenzene (6), pentafluorobenzene (7) (at 150 °C), octafluorotoluene (8) and pentafluoropyridine (9) (at 20 °C) react with phosphine 2 without a solvent almost quantitatively under fluorine 1,4-disubstitution (for 6) or monosubstitution (for 7-9) by the Ph2P group to give the corresponding (polyfluoroaryl)diphenylphosphines in 50-60% (for 6-8) and 95% (for 9) isolated yields. The regio and substrate selectivities exhibited by 3-5 in the reactions of the single substrates and in competitive reactions of 3 vs. 4 with 1 or 2 and 4 vs. 5 with 2 indicate relative fluorine substituent rate factors fo-F > fm-F consistent with the concerted ANDN mechanism which is supported by high level quantum chemical DFT-studies for the reactions of the substrates 3 and 4 with 1, 2 and 10 as well as for 6 with 2.
- Zhivetyeva,Goryunov,Bagryanskaya,Grobe,Shteingarts,Würthwein
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- Discovery of chemoselective and biocompatible reactions using a high-throughput immunoassay screening
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An immunoassay-based method was used to screen numerous combinations of dipoles and dipolarophiles for their ability to undergo chemoselective and biocompatible [3+2] cycloaddition reactions. The approach fulfills most of the requirements of the click concept and led to the discovery of a copper-catalyzed reaction that generates pyrazoles from sydnone and alkyne reagents. Copyright
- Kolodych, Sergii,Rasolofonjatovo, Evelia,Chaumontet, Manon,Nevers, Marie-Claire,Creminon, Christophe,Taran, Frederic
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supporting information
p. 12056 - 12060
(2013/12/04)
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- A2B ADENOSINE RECEPTOR ANTAGONISTS
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Disclosed are novel compounds that are A2B adenosine receptor antagonists having the following structure (I) wherein R1 and R2 are independently chosen from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and optionally substituted heteroaryl, and R4 is an optionally substituted heteroaryl moiety. The compounds of the invention are useful for treating various disease states, including asthma, chronic obstructive pulmonary disorder, pulmonary inflammation, emphysema, diabetic disorders, inflammatory gastrointestinal tract disorders, immunological/inflammatory disorders, cardiovascular diseases, neurological disorders, and diseases related to angiogenesis.
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Page/Page column 41
(2008/06/13)
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- A novel series of potent and selective small molecule inhibitors of the complement component C1s
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Activation of the classical pathway of complement has been implicated in disease states such as hereditary angioedema, ischemia-reperfusion injury and acute transplant rejection. The trypsin-like serine protease C1s represents a pivotal upstream point of
- Subasinghe, Nalin L.,Ali, Farah,Illig, Carl R.,Rudolph, M. Jonathan,Klein, Scott,Khalil, Ehab,Soll, Richard M.,Bone, Roger F.,Spurlino, John C.,DesJarlais, Renee L.,Crysler, Carl S.,Cummings, Maxwell D.,Morris Jr., Philip E.,Kilpatrick, John M.,Babu, Y. Sudhakara
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p. 3043 - 3047
(2007/10/03)
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- Generation of NH-azomethine imine intermediates through the 1,2-hydrogen shift of hydrazones and their intermolecular cycloaddition reaction with olefinic dipolarophiles
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The thermal 1,2-hydrogen shift of the hydrazone generates the NH-azomethine imine intermediate in the 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde system under mild conditions. Therein, the resulting NH-azomethine imine should be stabilized by forming an internal hydrogen bond with the carbonyl oxygen at the 4-position. Its smooth stereoselective intermolecular cycloaddition reaction with olefinic dipolarophiles giving pyrazolidine derivatives is discussed.
- Noguchi, Michihiko,Matsumoto, Satoshi,Shirai, Masashi,Yamamoto, Hidetoshi
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p. 4123 - 4133
(2007/10/03)
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- N-1 Substituted Ethyl 4-Pyrazolecarboxylates: Synthesis and Spectroscopic Investigations
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The synthesis of various N-1 substituted ethyl 4-pyrazolecarboxylates via reaction of ethyl 2-formyl-3-oxopropionate (= ethoxycarbonylmalondialdehyde) with appropriately substituted hydrazines is described.Moreover, detailed nmr-spectroscopic investigations with the title compounds are presented.
- Holzer, Wolfgang,Seiringer, Gertrud
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p. 865 - 872
(2007/10/02)
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- PHOTOCHEMICAL SYNTHESIS OF 4-ETHOXYCARBONYL-5-HYDROXYPYRAZOLES
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The photochemical decomposition of 4-ethoxycarbonyl-5-diazopyrazoles in tetrafluoroboric acid results in corresponding 4-ethoxycarbonyl-5-hydroxypyrazoles (V-VII).The irradiation of the diazocompound in dioxane, toluene or tetrahydrofurane proceeds with a reductive decomposition producing corresponding 4-ethoxycarbonylpyrazole (VIII) as the main photoproduct.
- Spassova, Maria K.,Zakharieva, Rossitza D.
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p. 196 - 199
(2007/10/02)
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- Nonaqueous Diazotation of 5-Amino-1-aryl-1H-pyrazole-4-carboxylate Esters
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5-Amino-1-aryl-1H-pyrazole-4-carboxylate esters are converted to the corresponding desamino, chloro, bromo, iodo, and methylthio esters by processes involving nonaqueous diazotation.Diazotizing agents are alkyl nitrites except in the case of chlorine wher
- Beck, James R.,Gajewski, Robert P.,Lynch, Michael P.,Wright, Fred L.
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p. 267 - 270
(2007/10/02)
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