- Continuous-Flow Electrosynthesis of Benzofused S-Heterocycles by Dehydrogenative C?S Cross-Coupling
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Reported herein is the synthesis of benzofused six-membered S-heterocycles by intramolecular dehydrogenative C?S coupling using a modular flow electrolysis cell. The continuous-flow electrosynthesis not only ensures efficient product formation, but also obviates the need for transition-metal catalysts, oxidizing reagents, and supporting electrolytes. Reaction scale-up is conveniently achieved through extended electrolysis without changing the reaction conditions and equipment.
- Huang, Chong,Qian, Xiang-Yang,Xu, Hai-Chao
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supporting information
p. 6650 - 6653
(2019/04/26)
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- Soft-Hard Acid/Base-Controlled, Oxidative, N-Selective Arylation of Sulfonanilides via a Nitrenium Ion
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In iodine(III)-catalyzed, dehydrogenative arylations of sulfonanilides, the functionalization of C-C bonds is preferred over the functionalization of C-N bonds. Herein, an unprecedented N-selective arylation of sulfonanilides using soft-hard acid-base (SHAB) control by a nitrenium ion over a carbenium ion is reported. Treatment of sulfonanilides with iodine(III) led to the formation of nitrenium ions (soft), which preferentially react with biphenyls (soft) over bimesityl (hard) to generate C-N bonds. The iodine(III) was generated in situ by using PhI and mCPBA at room temperature.
- Maiti, Saikat,Mal, Prasenjit
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p. 1340 - 1347
(2018/02/09)
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- 1,3,4-OXADIAZOLE SULFONAMIDE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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The present invention relates to novel compounds represented by the formula I having histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions containing the same, a method for treating diseases using the composition, and methods for preparing the novel compounds. (I) The novel compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof according to the present invention have histone deacetylase (HDAC) inhibitory activity and are effective for the prevention or treatment of HDAC6-mediated diseases.
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Paragraph 1087; 1088; 1089
(2017/02/24)
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- An Organic Intermolecular Dehydrogenative Annulation Reaction
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The discovery of a direct method for the synthesis of three-ring heterocyclic carbazoles from unactivated arenes and anilides by a metal-free (organic) intermolecular dehydrogenative annulation reaction under ambient laboratory conditions is reported. Iodine(III) was used as the sole reagent either stoichiometrically from inexpensive phenyliodine diacetate or organocatalytically by in situ generation from PhI-mCPBA. In a single step, three C(sp2)-H bonds and one N(sp3)-H bond are functionalized from two different arenes for tandem C-C and C-N bond formation reactions.
- Maiti, Saikat,Achar, Tapas Kumar,Mal, Prasenjit
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supporting information
p. 2006 - 2009
(2017/04/28)
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- Carbazole-containing sulfonamides and sulfamides: Discovery of cryptochrome modulators as antidiabetic agents
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A series of novel carbazole-containing sulfonamides and sulfamides were synthesized. A structure-activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the results of efficacy studies in diet-induced obese (DIO) mice, and the desired pharmacokinetic parameters, compound 41 was selected for further profiling.
- Humphries, Paul S.,Bersot, Ross,Kincaid, John,Mabery, Eric,McCluskie, Kerryn,Park, Timothy,Renner, Travis,Riegler, Erin,Steinfeld, Tod,Turtle, Eric D.,Wei, Zhi-Liang,Willis, Erik
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p. 757 - 760
(2016/05/24)
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- Palladium-Catalyzed cascade sp2 c?H bond functionalizations allowing one-Pot access to 4?Aryl-1,2,3,4-tetrahydroquinolines from n?Allyl?N?arylsulfonamides
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We have developed a palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp2)?C(sp3) bonds were formed via activation of C(sp2)?H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents on both reaction partners.
- Yuan, Kedong,Soule, Jean-Francois,Dorcet, Vincent,Doucet, Henri
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p. 8121 - 8126
(2018/05/23)
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- Oxidative fluorination of N-arylsulfonamides
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We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tert-butyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF·pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho- and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[18F]fluorophenyl sulfonamides under carrier added conditions.
- Buckingham, Faye,Calderwood, Samuel,Checa, Bego?a,Keller, Thomas,Tredwell, Matthew,Collier, Thomas Lee,Newington, Ian M.,Bhalla, Rajiv,Glaser, Matthias,Gouverneur, Véronique
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- Low catalyst loadings for ligand-free copper(I)-oxide-catalyzed N-arylation of methanesulfonamide in water
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A simple and practical protocol for the cross-coupling of methanesulfonamide and aryl iodides under ligand-free copper(I)-oxide-catalyzed conditions in water is reported. The method allows the preparation of a wide variety of synthetically useful N-arylated methanesulfonamides in good to excellent yields (up to 90 %) under the optimized conditions. A convenient and efficient ligand-free method using a copper(I) oxide catalyst at 130 °C in water was developed for the N-arylation of methanesulfonamide with aryl iodides. A variety of functionalized aliphatic and cyclic sulfonamides were coupled with different substituted aryl halides to give the corresponding N-arylated products in good to excellent yields under the optimized conditions. Copyright
- Tan, Bryan Yong-Hao,Teo, Yong-Chua,Seow, Ai-Hua
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p. 1541 - 1546
(2014/03/21)
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- Low Catalyst Loadings for Ligand-Free Copper(I)-Oxide-Catalyzed N-Arylation of Methanesulfonamide in Water
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A simple and practical protocol for the cross-coupling of methanesulfonamide and aryl iodides under ligand-free copper(I)-oxide-catalyzed conditions in water is reported. The method allows the preparation of a wide variety of synthetically useful N-arylated methanesulfonamides in good to excellent yields (up to 90 %) under the optimized conditions.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua,Seow, Ai-Hua
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p. 1541 - 1546
(2015/10/05)
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- Mild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides
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An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO2-source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under
- Kloeckner, Ulrich,Nachtsheim, Boris J.
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supporting information
p. 10485 - 10487
(2014/09/29)
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- Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones
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Adducts from the intermolecular radical addition of N-xanthylacetyl-N- methanesulfanilides to Boc-protected allylamine undergo ring closure with loss of a methanesulfonyl radical to give benzazepin-2-ones. Upon deprotection and exposure to triethylamine,
- Charrier, Nicolas,Liu, Zhibo,Zard, Samir Z.
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supporting information; experimental part
p. 2018 - 2021
(2012/06/01)
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- Convenient synthesis of primary sulfonamides
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An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.
- Greenfield, Alexander,Grosanu, Cristina
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body text
p. 6300 - 6303
(2009/04/06)
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- Base-free monosulfonylation of amines using tosyl or mesyl chloride in water
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A mild and efficient procedure has been developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.
- Kamal, Ahmed,Reddy, J. Surendranadha,Bharathi, E. Vijaya,Dastagiri
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p. 348 - 353
(2008/09/17)
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- β-cyclodextrin-catalyzed monosulfonylation of amines and amino acids in water
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A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.
- Sridhar,Srinivas,Kumar, V. Pavan,Narender,Rao, K. Rama
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p. 1873 - 1876
(2008/09/16)
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- Studies on development of sufficiently chemoselective N-acylation reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides
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A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd.
- Kondo, Kazuhiro,Sekimoto, Erika,Nakao, Junko,Murakami, Yasuoki
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p. 5843 - 5856
(2007/10/03)
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- Fluorination of Aromatic Derivatives with Fluoroxytrifluoromethane and Bis(fluoroxy)difluoromethane
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Fluoroxytrifluoromethane (CF3OF) and bis(fluoroxy)difluoromethane CF2(OF)2 are formed by the reaction of F2 with CO and CO2, respectively, over a CsF catalyst in a continouous-stream process.Both reagents react with aromatic substrates by an electrophilic substitution mechanism to yield fluoro-substituted derivatives.Fluorobenzene is produced in good yield from benzene, and aniline derivatives afford monofluorination products.Acetanilide (1), N-phenylmethanesulfonamide (2), α,α,α-trifluoroacetanilide (3), and 1,1,1-trifluoro(N-phenyl)methanesulfonamide (4) react with either reagent to yield mixtures of o- and p-fluoro-substituted derivatives.Solvent effects and competitive rate experiments demonstrate a preference for ortho substitution, especially in aprotic, nonpolar solvents.With particular substrates, these fluorinating agents are of practical synthetic utility, e.g., 2-fluoro-4-(trifluoromethyl)aniline is produced in high yield by fluorinating the intermediate 4-(trifluoromethyl)acetanilide (6) with CF3OF.Activated substrates such as toluene, xylenes, anisole, and cresols give mixtures of products which reduce the synthetic utility of these reagents.Nitrobenzene is fairly unreactive toward CF3OF and gives low yields of substitution products.
- Fifolt, Michael J.,Olczak, Raymond T.,Mundhenke, Rudolph F.
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p. 4576 - 4582
(2007/10/02)
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- Substituent effects in infrared spectroscopy-VII. Meta and para substituted methanesulphonanilides
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Substituent effects on the NH frequencies of the conformers of methanesulphonanilides, their cyclic dimers and their hydrogen bonded complexes with acetonitrile have been analysed by means of the Hammet equation.An electron-withdrawing substituent may either increase or decrease ν(NH) in the XC6H4NHY series according to the electronic nature of the Y group.This can be explained by the non-monotonic dependence of the NH stretching frequency on the ionic character of the NH bond.
- Laurence, C.,Berthelot, M.,Lucon, M.,Tsuno, Y.
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p. 791 - 796
(2007/10/02)
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