- Lewis Base-Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides
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A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene-BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.
- Yu, You-Jie,Zhang, Feng-Lian,Cheng, Jie,Hei, Jing-Hao,Deng, Wei-Ting,Wang, Yi-Feng
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supporting information
p. 24 - 27
(2018/01/17)
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- Development of Quinoline-2,4(1H,3H)-diones as Potent and Selective Ligands of the Cannabinoid Type 2 Receptor
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The cannabinoid type 2 receptors (CB2Rs) play crucial roles in inflammatory diseases. There has been considerable interest in developing potent and selective ligands for CB2R. In this study, quinoline-2,4(1H,3H)-dione analogs have been designed, synthesized, and evaluated for their potencies and binding properties toward the cannabinoid type 1 receptor (CB1R) and CB2R. C5- or C8-substituted quinoline-2,4(1H,3H)-diones demonstrate CB2R agonist activity, while the C6- or C7-substituted analogs are antagonists of CB2R. In addition, oral administration of 21 dose-dependently alleviates the clinical symptoms of experimental autoimmune encephalomyelitis in a mouse model of multiple sclerosis and protects the central nervous system from immune damage. Furthermore, the interaction modes predicted by docking simulations and the 3D-QSAR model generated with CoMFA may offer guidance for further design and modification of CB2R modulators.
- Han, Shuang,Zhang, Fei-Fei,Qian, Hai-Yan,Chen, Li-Li,Pu, Jian-Bin,Xie, Xin,Chen, Jian-Zhong
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p. 5751 - 5769
(2015/08/24)
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- C-N bond formation catalysed by CuI Bonded to polyaniline nanofiber
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Polyaniline nanofiber as a macroligand for the supported cuprous iodide catalyst (CuI-PANInf) has been developed for the coupling of aryl halides (including aryl chlorides) with aliphatic, aromatic, and N(H)-heterocyclic amines under ambient conditions (80 °C for aryl chlorides) has been developed. This simple and efficient method for coupling reactions is highly versatile, convenient, and also the catalyst can be used for several cycles with good-to-excellent yields.
- Arundhathi, Racha,Kumar, Desitti Chaitanya,Sreedhar, Bojja
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supporting information; experimental part
p. 3621 - 3630
(2010/08/20)
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- Iron/copper-cocatalyzed ullmann N,O-arylation using FeCl3, CuO, and rac-1,1′-Binaphthyl-2,2′-diol
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We have developed an efficient and inexpensive bimetallic catalyst FeCl3, CuO, and rac-BINOL that could promote N,O-arylation of aliphatic, arylamines, and phenols. The cross-coupling reaction conditions have high tolerance of various functional groups. This versatile and efficient iron/copper-cocatalyst can widely be used in the synthesis of the compounds containing (aryl)C-N or (aryl)C-O(aryl) bond. Georg Thieme Verlag Stuttgart.
- Wang, Zhe,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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body text
p. 2540 - 2546
(2009/04/12)
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- CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature
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We have developed an efficient and readily available catalyst system CuBr/racemic BINOL ( 1,1′-binaphthyl-2,2′-diol) that catalyzes N-arylation of aliphatic amines at room temperature, and this inexpensive catalyst system is of high selectivity and tolerance toward various functional groups in the substrates.
- Jiang, Deshou,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 672 - 674
(2007/10/03)
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- A mild and efficient method for copper-catalyzed Ullmann-type N-arylation of aliphatic amines and amino acids
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An efficient and general protocol for copper-catalyzed N-arylation of aliphatic amines and amino acids has been developed using aryl iodides under mild conditions (coupling temperature at 25-35°C). For the N-(o-nitrophenyl) amino acid derivatives, subsequent reduction of the nitro group in the presence of tin(II) chloride resulted in 3,4-dihydroquinoxalin-2(1H)-one derivatives in good yields. Georg Thieme Verlag Stuttgart New York.
- Jiang, Qun,Jiang, Deshou,Jiang, Yuyang,Fu, Hua,Zhao, Yufen
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p. 1836 - 1842
(2008/02/10)
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- Radical cyclisations of imines and hydrazones
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Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.
- Bowman, W. Russell,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
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p. 7959 - 7980
(2007/10/02)
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