7510-48-7Relevant academic research and scientific papers
Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans
Chen, Xingyu,Lu, Sixian,Deng, Ping,Chang, Xiaoqiang,Zhao, Yifan,Ma, Yue,Zhang, Dong,Xia, Fei,Yang, Lan,Wang, Jigang,Sun, Peng
supporting information, p. 94 - 102 (2021/10/05)
A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance. (Figure presented.).
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium
Jiang, Xiaolan,Zhang, Kaili,Zhao, Rongrong,Bai, Die,Wang, Jinlong,Li, Binbin,Liu, Qixing,Zhou, Haifeng
supporting information, (2020/09/10)
A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.
Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions
Youn, So Won,Kim, Young Ho,Jo, Yoon Hyung
supporting information, p. 462 - 468 (2019/01/04)
A palladium-catalyzed aerobic C?H amidation of N-Ts-2-amino-3′-hydroxylbiaryls has been developed to afford a diverse range of 1-hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, a
Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex
Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
supporting information, p. 1098 - 1102 (2019/05/16)
The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.
Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones
Liu, Teng,Liu, Jianjun,Shen, Xianfu,Xu, Jianbin,Nian, Beifang,He, Ni,Zeng, Shunqun,Cheng, Feixiang
, p. 1365 - 1376 (2019/03/08)
An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.
Differentiation of isomeric haloanilines by tosylation in combination with electrospray ionization mass spectrometry
Wang, Shanshan,Cheng, Yuanyuan,Chen, Mengmeng,Jiang, Kezhi
, p. 337 - 343 (2018/07/31)
Differentiation of the isomeric haloanilines still remains a challenging and?necessary?analytic task due to their identical retention time in chromatography and similar mass spectra. In this work, p-tosylation of haloanilines by reaction of haloanilines with p-toluenesulfonyl chloride resulted in the corresponding N-tosyl haloanilines. Fragmentation of protonated N-tosyl haloanilines in electrospray ionization tandem mass spectrometry (ESI-MS/MS) mainly resulted in tosyl cation, haloaniline radical cation, and halohydroxyaniline radical cation. The MS/MS of the three group isomeric derivatives showed significant difference in abundance distribution of these product ions, respectively. Theoretical calculations showed that the stability of the ion-neutral complex (INC) is a key factor influencing the relative intensity of the product ions. The three group isomeric derivatives were also separated by high performance liquid chromatograph (HPLC) at conventional conditions. p-Tosylation combined tandem MS (or HPLC) technique were carried out to realize the differentiation of isomeric haloanilines.
A convenient and benign synthesis of sulphonamides in PEG-400
Das, Pranab Jyoti,Sarmah, Bhaskar
, p. 189 - 191 (2015/02/19)
A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.
Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
, p. 8010 - 8019 (2015/03/18)
The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
Identification of novel glycine sulfonamide antagonists for the EP1 receptor
McKeown, Stephen C.,Hall, Adrian,Blunt, Richard,Brown, Susan H.,Chessell, Iain P.,Chowdhury, Anita,Giblin, Gerard M.P.,Healy, Mark P.,Johnson, Matthew R.,Lorthioir, Olivier,Michel, Anton D.,Naylor, Alan,Lewell, Xiao,Roman, Shilina,Watson, Stephen P.,Winchester, Wendy J.,Wilson, Richard J.
, p. 1750 - 1754 (2007/10/03)
A high-throughput screen targeting the EP1 receptor identified non-acidic glycine sulfonamide derivative 2a with a pKi of 6.2. Analogue synthesis allowed a thorough investigation of the structure-activity relationship (SAR) and led to a 100-fold increase in recombinant potency.
