3897-39-0Relevant academic research and scientific papers
Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives
Cabanal-Duvillard, Isabelle,Berrien, Jean-Francois,Royer, Jacques,Husson, Henri-Philippe
, p. 5181 - 5184 (1998)
Bromination and bromohydroxylation of oxazolidinones derived from cyclohexadiene have been studied in order to synthetize (±)-epibatidine 18. Bromohydroxylation of compound 2 led to a polyfunctionalized halohydrin 11a which could be further cyclized to azabicyclo[2.2.1]heptan-2-one 16 already described as a precursor of epibatidine 18.
2,2-Dimethyl-3-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1,3,2-benzoxazasilole: synthesis, properties, and structure
Nikonov, A. Yu.,Sterkhova,Lazareva
, p. 386 - 390 (2021)
2,2-Dimethyl-3-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1,3,2-benzoxazasilole was synthesized by the reaction of N-(2-hydroxyphenyl)-4-methylbenzenesulfonamide with dimethyl-dichlorosilane or N, N-bis(dimethylamino)dimethylsilane in 68 and 96% yield, respectively. The structure of the new compound was assigned using NMR and IR spectroscopy and confirmed by X-ray diffraction. In the crystal, the silole molecules are linked to each other by short O?H-C contacts (～2.6 ?) between the oxygen atoms of the bicyclic moiety and the methyl hydrogen atoms of adjacent molecules.
Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study
Wang, Yi,Chen, Xiaoli,Lin, Shuang,Gao, Hui,Liu, Fu-Xiaomin,Zhou, Zhi,Yi, Wei
supporting information, (2022/01/08)
ortho-Sulfonamide phenols represent a class of attractive structural motifs in medicinal and synthetic chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted
Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels-Alder Reaction
Beccalli, Egle M.,Giofrè, Sabrina,Keller, Manfred,Lo Presti, Leonardo,Molteni, Letizia
supporting information, p. 7698 - 7702 (2021/10/25)
The Pd(II)-catalyzed reaction of N-allyl-2-aminophenols in the presence of PhI(OCOR)2 as the oxidant resulted in an alkoxyacyloxylation process, with the formation of functionalized dihydro-1,4-benzoxazines. The reaction performed in the absence of pallad
Pd(II)-Catalyzed Enantioselective Ring-Contraction for the Construction of 1,4-Benzoxazines
Ye, Chenghao,Gao, Feng,Wei, Haipeng,Chen, Jianzhong,Yang, Guoqiang,Yuan, Qianjia,Zhang, Wanbin
supporting information, p. 16573 - 16581 (2021/11/18)
Enantioselective ring-contraction reactions have not been widely reported. We have developed an enantioselective ring contraction of 5,6-dihydro-2H-benzo[b][1,4]oxazocines, affording enantiomerically enriched 3,4-dihydro-2H-1,4-benzoxazine derivatives as
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.
Synthesis and structural features of N-[(2-(trimethylsilyl)oxy)phenyl]-arylsulfonamides
Nikonov, Alexey Yu,Sterkhova, Irina V.,Serykh, Valeriy Yu,Kolyvanov, Nikita A.,Lazareva, Natalya F.
, (2019/08/12)
N-[(2-(Trimethylsilyl)oxy)phenyl]-4-methylbenzenesulfonamide and N-[(2-trimethylsilyloxy)phenyl]-4-chlorobenzenesulfonamide were prepared by two different methods. Their structures were studied by X-ray single-crystal analysis and DFT calculations includi
Solvent-Controlled Pd(II)-Catalyzed Aerobic Chemoselective Intermolecular 1,2-Aminooxygenation and 1,2-Oxyamination of Conjugated Dienes for the Synthesis of Functionalized 1,4-Benzoxazines
Wen, Ke,Wu, Zhengxing,Huang, Banruo,Ling, Zheng,Gridnev, Ilya D.,Zhang, Wanbin
, p. 1608 - 1612 (2018/03/23)
Pd(II)-catalyzed intermolecular 1,2-aminooxygenation and 1,2-oxyamination of conjugated dienes have been developed. The chemoselective preparation of a variety of 2-functionalized and 3-functionalized 1,4-benzoxazine derivatives was accomplished via the a
Palladium-catalyzed oxamidation of alkenes: A new approach to benzoxazolidines
Panda, Niranjan,Yadav, Sushree Arpitabala
, p. 1497 - 1504 (2018/02/21)
A novel palladium catalyzed protocol for the synthesis of benzoxazolidine by the reaction sulfamidophenol and terminal alkene was developed. This oxamidation process is simple and does not require any ligand, base or inert atmosphere for the overall trans
A Facile Route to Ortho-Hydroxyanilnes through an IrIII-Catalyzed Direct C?H Amidation of 2-Phenoxypyridines
Wang, Lianhui,Yang, Zi,Yang, Mengqi,Tian, Miaodou,Kuai, Changsheng,Cui, Xiuling
, p. 2634 - 2643 (2017/09/13)
A highly efficient and regioselective IrIII-catalyzed C?H amidation of 2-phenoxypyridines has been developed by using sulfonyl azides as an amino source. The amidated products were provided in good-to-excellent yields with broad functional-group tolerance. Furthermore, the 2-pyridyl moiety in the amidated products could be readily removed, thus offering an efficient route to synthetically useful ortho-hydroxyanilnes, which are important building blocks in organic synthesis.
