- UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides
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A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.
- Chen, Ming,Yang, Chao,Wang, Yanpei,Li, Dazhi,Xia, Wujiong
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Read Online
- Direct Introduction of Sulfonamide Groups into Quinoxalin-2(1H)-ones by Cu-Catalyzed C3-H Functionalization
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Direct sulfonamidation of quinoxalin-2(1H)-one derivatives has been developed using a readily available Cu salt as the catalyst and inexpensive ammonium persulfate as the oxidant in moderate conditions. Owing to the feature of handy operation and good functional group tolerance, this method provides a convenient and efficient access to curative 3-sulfonamidated quinoxalin-2(1H)-one scaffolds.
- Tan, Yushi,Liu, Boyan,Han, Ya-Ping,Zhang, Yuecheng,Zhang, Hong-Yu,Zhao, Jiquan
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Read Online
- N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]
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A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.
- Liu, Peng,Tung, Nguyen Thanh,Xu, Xiangchao,Yang, Jiazhi,Li, Feng
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p. 2621 - 2631
(2021/02/27)
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- Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate
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An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete selectivities and functional group friendliness. Furthermore, the synthesized catalyst could be recycled by simple filtration without obvious loss of catalytic activity after sixth cycle. Notably, this research exhibited the potential of covalent triazine framework-supported transition metal catalysts for hydrogen autotransfer process.
- Liu, Peng,Yang, Jiazhi,Ai, Yao,Hao, Shushu,Chen, Xiaozhong,Li, Feng
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p. 281 - 290
(2021/03/26)
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- Alkene Syn- And Anti-Oxyamination with Malonoyl Peroxides
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Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2 tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R3 = CO2Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.
- Curle, Jonathan M.,Perieteanu, Marina C.,Humphreys, Philip G.,Kennedy, Alan R.,Tomkinson, Nicholas C. O.
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supporting information
p. 1659 - 1664
(2020/02/13)
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- N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst
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The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed activation of methanol as a C1 source for the construction of the C-N bond in aqueous solution.
- Han, Xingyou,Li, Feng,Liu, Peng,Meng, Chong,Tung, Nguyen Thanh
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p. 5815 - 5824
(2020/05/26)
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- Method for synthesizing N-methyl sulfonamide in water
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The invention discloses a method N - for synthesizing,methylsulfamide in water, by using a transition metal iridium catalyst to catalyze N - methylation reaction. by using a non-toxic and harmless water as a solvent, to avoid using the organic agent; to react only as a byproduct, without an environmental hazard; reaction temperature with respect to the previous strip more mild; and have a wide application prospect; with high selectivity, reaction atomic economy.
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Paragraph 0110-0114
(2020/03/12)
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- Highly efficient synthesis of aryl ketones by PEPPSI-palladium catalyzed acylative Suzuki coupling of amides with diarylborinic acids
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An improved acylative cross-coupling of various N-methyl-N-tosyl amides with diarylborinic acids for synthesis of aryl ketones is developed. In most cases, aryl ketones could be obtained in excellent yields by using 1 mol% 2,6-diisopropylphenylimidazolylidene and 3-chloropyridine co-supported palladium chloride as catalyst in the presence of 3 equiv. K2CO3 as base in refluxing THF. The readily prepared and cost-effective substrates, N-methyl-N-tosylamides and diarylborinic acids, and the commercially available catalyst system promise a practical and efficient access to aryl ketones.
- Wang, Chen,Huang, Lingyun,Wang, Fengze,Zou, Gang
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supporting information
p. 2299 - 2301
(2018/05/16)
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- Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach
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A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).
- Polidano, Kurt,Allen, Benjamin D. W.,Williams, Jonathan M. J.,Morrill, Louis C.
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p. 6440 - 6445
(2018/07/25)
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- Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group
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A general Pd-catalyzed Suzuki-Miyaura cross-coupling of N-mesylamides with arylboronic acids by selective N-C cleavage has been developed. The presented results represent the first example of a transition-metal-catalyzed cross-coupling of amides activated by an atom-economic, cheap, and benign mesyl group. The reaction delivers arylated products featuring a range of useful functional groups by chemoselective cleavage of the amide N-C bond with high efficiency. Both the scope and the origin of high selectivity are discussed. A beneficial effect of the N-mesyl substituent on the bond activation in acyclic amides is presented.
- Liu, Chengwei,Liu, Yongmei,Liu, Ruzhang,Lalancette, Roger,Szostak, Roman,Szostak, Michal
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supporting information
p. 1434 - 1437
(2017/03/23)
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- N-Methylation of Amines with Methanol Catalyzed by a Cp?Ir Complex Bearing a Functional 2,2′-Bibenzimidazole Ligand
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A new type of Cp?Ir complex bearing a functional 2,2′-bibenzimidazole ligand was designed, synthesized, and found to be a highly effective and general catalyst for the N-methylation of a variety of amines with methanol in the presence of a weak base (0.3 equiv of Cs2CO3).
- Liang, Ran,Li, Shun,Wang, Rongzhou,Lu, Lei,Li, Feng
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supporting information
p. 5790 - 5793
(2017/11/10)
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- Mono-N-methylation of anilines with methanol catalyzed by a manganese pincer-complex
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The selective mono-N-methylation of anilines derivatives was achieved under mild conditions using inexpensive methanol as C1 source. Under hydrogen borrowing conditions, using a tridentate PN3P manganese pre-catalyst (5?mol%), a catalytic amount of base (20?mol%), for 24?h at 120?°C, a large variety of anilines derivatives was methylated in good to excellent yield. Mechanistic investigations allowed us to isolate and characterize by X-ray diffraction studies a de-aromatized manganese intermediate.
- Bruneau-Voisine, Antoine,Wang, Ding,Dorcet, Vincent,Roisnel, Thierry,Darcel, Christophe,Sortais, Jean-Baptiste
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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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- COMPOUNDS FOR REGULATING FAK AND/OR SRC PATHWAYS
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The present application provides novel optionally substituted fused pyridine and pyrimidine bicyclic compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating FAK and/or Src activity by administering a therapeutically effective amount of one or more of the compounds to a subject. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the FAK and/or Src pathway. Advantageously, these compounds perform as dual FAK and/or Src inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.
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Page/Page column 82
(2015/03/28)
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- Establishment of heterolytic and homolytic Y-NO2 bond dissociation energy scales of nitro-containing compounds in acetonitrile: Chemical origin of NO2 release and capture
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(Chemical Equation Presented) The first heterolytic and homolytic N(O)-NO2 bond dissociation energy scales of three types Y-nitro (Y = N, O) compounds and corresponding radical anions in acetonitrile were established by using titration calorimetry combined with relevant electrochemical data through proper thermodynamic cycles.
- Li, Xin,Zhu, Xiao-Qing,Zhang, Fan,Wang, Xiao-Xiao,Cheng, Jin-Pei
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p. 2428 - 2431
(2008/09/20)
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- Novel compounds and methods for synthesis and therapy
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Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.
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- Cerium(III) chloride-mediated reactions of sulfonamide dianions
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Presented here is the first report on the ability of cerium(III) chloride to mediate high-yielding and, oftentimes, highly diastereoselective additions of N-benzyl-α, N-dilithio methanesulfonamide to aldehydes and ketones of biological importance. Smooth addition was effected to base-sensitive substrates such as Fmoc-protected alaninal, citral, 5-cholesten-3-one, uridine 5′-aldehyde, 3′-ketouridine, and 3′-ketothymidine. The reaction was chemoselective for aldehydes in the presence of nitriles. Acetoxy groups are labile and thus not suitable protecting groups for alcohols under these conditions. N-Benzyl-α, N-dilithio methanesulfonamide was found to be of sufficient basicity to cause enolate formation with sensitive substrates, such as 1-phenylacetone. However, the addition of cerium(III) chloride mediated the basicity of the dianion and suppressed enolate formation in these cases. Further, cerium(III) has general utility for the addition of various N-aliphatic/aromatic methanesulfonamide dianions to 3′-ketouridine.
- Johnson II, David C.,Widlanski, Theodore S.
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p. 5300 - 5309
(2007/10/03)
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- Compounds and methods for synthesis and therapy
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Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.
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- Lyophilized thioxanthenone antitumor agents
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Disclosed are reconstituted lyophilized formulations for the treatment of mammalian tumors comprising a thioxanthenone antitumor agent in combination with mannitol or sucrose as a stabilizer in a lactate buffer.
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- Process for the preparation of sulfonylureas
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Herbicidal sulfonylureas of the formula I, STR1 in which X is --O--, --O--NR2 -- or --SO2 --NR2 --, Y is --N-- or CH, R1 is (substituted) alkyl, (substituted) alkenyl or (substituted) alkynyl, or else, where X=O, (substituted) phenyl, R2 is H, alkyl, alkenyl, alkynyl or cycloalkyl, R3, R4 are H, (substituted) alkyl or (substituted) alkoxy, halogen, alkylthio, alkylamino or dialkylamino and R5, R6 are H or alkyl, and their salts with acids or bases, are prepared by reacting compounds of the formula II STR2 with compounds of the formula III STR3
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- Thioxanthenone antitumor agents
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1-[[(Dialkylamino)alkyl]amino]-4-substituted-thioxanthen-9-ones are disclosed as antitumor agents. Compositions containing the thioxanthenones and methods of treating tumors and cancer in mammals with the thioxanthenones are also disclosed.
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- Certain N-(R-sulfonyl) phosphonamidothioates and dithioates
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Compounds of the formula STR1 wherein the symbols have assigned meanings, and their use as insecticides and/or miticides.
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- HOMOLYTIC DISPLACEMENT AT CARBON CENTRES. XII. REGIOSPECIFIC FORMATION OF N-ALLYL AND N-CYCLOPROPYLCARBINYL SULPHONAMIDES AND OF ALLYL AND CYCLOPROPYL HALIDES IN THE REACTION OF N-HALOGENO COMPOUNDS WITH ORGANOCOBALOXIMES
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Several but-3-enyl and allylcobaloximes react regiospecifically with N-chloro-N-methyl sulphonamides to give N-cyclopropylcarbinyl- or rearranged N-allyl-N-methyl sulphonamides, by a process which is believed to take place by the attack of an N-centred radical at the terminal unsaturated carbon of the organic ligand, with displacement of cobaloxime(II).In contrast, N-bromoacetamide and several other N-halogenoimides react regiospecifically to the cyclopropylcarbinyl halide or the rearranged allyl halide by a process in which a halogen-containing free radical species attacks the terminal unsaturated carbon of the organocobaloxime.
- Johnson, Michael D.,Lampman, Gary M.,Koops, Roger W.,Gupta, B. Das
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p. 281 - 288
(2007/10/02)
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- The Reaction of N-Alkylhydroxamic Acids with Sulphinyl Chlorides
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The reaction of several N-methylhydroxamic acids with methane- and benzene-sulphinyl chloride is shown to give an isolatable O-sulphinylated intermediate (IV) below 0 deg C.The intermediates decompose at ambient temperatures with simultaneous N-O and S-O bond fission to give the isomeric N-acyl-N-methylsulphonamide (V) and N-methyl-O-sulphonylhydroxamic acid (VI) by in-cage and free pair radical recombination. 1H and 13C n.m.r. spectra show strong polarisations in both sulphonamide (V) and O-sulphonylhydroxamic acid (VI), indicating radical cage mechanisms.In addition, a strong e.s.r. signal was observed due to the N-acyl- N-methylnitroxyl radical (X).
- Banks, Malcolm R.,Hudson, Robert F.
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p. 1211 - 1216
(2007/10/02)
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- Vibrational spectra of N-methylmethanesulfonamide and its C- and N-deuterated compounds
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The i.r. and Raman spectra of the eight isotopic N-methylmethanesulfonamides have been recorded in the liquid state.The i.r. spectrum of the undeuterated compound has been recorded the in liquid state at different temperatures and in the crystalline state, but no spectral changes attributable to the rotational isomerism have been observed.The normal coordinate calculation has been carried out for the most probable conformation, and the isotope shifts have been reproduced well.The force constants obtained have been transferred to the other possible conformers, and the conformation dependence of the vibrational frequencies has been discussed.
- Noguchi, Akihiro,Hanai, Kazuhiko,Okuda, Takachiyo
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p. 829 - 834
(2007/10/02)
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