- Single-Electron-Transfer-Induced C(sp3)-N Couplings via C-C Bond Cleavage of Cycloketoxime Esters
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A practical single-electron-transfer-induced selective C(sp3)-N coupling of cycloketoximes with anilines via C-C bond cleavage under copper-catalytic and synergetic photoredox/copper-catalytic reaction systems has been uncovered. These two powerful and simple protocols demonstrated excellent selectivity and good functional group compatibility without any base or ligand control. Preliminary mechanistic experiments indicated that a radical-mediated process was involved in these transformations.
- Shi, Zhuangzhi,Wang, Minyan,Zhao, Binlin
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- Copper-Catalyzed Cyanoalkylation of Amines via C-C Bond Cleavage: An Approach for C(sp3)-N Bond Formations
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The efficient copper-catalyzed cyanoalkylation of amines via C-C bond cleavage has been demonstrated. Distinctive features of this procedure involves mild conditions, broad range of nitrogen nucleophiles, high selectivity, and good functional group tolerance, thus providing a useful approach for the C(sp3)-N bond formations. Most importantly, this protocol is applicable to the late-stage functionalization of natural products, amino acid esters, and drugs. Mechanistic studies suggest that a radical intermediate was involved in this transformation.
- Yang, Lin,Zhang, Jia-Yu,Duan, Xin-Hua,Gao, Pin,Jiao, Jiao,Guo, Li-Na
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p. 8615 - 8629
(2019/08/30)
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- Microwave-assisted cyclizations promoted by polyphosphoric acid esters: A general method for 1-aryl-2-iminoazacycloalkanes
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The first general procedure for the synthesis of 5 to 7-membered 1-aryl-2-iminoazacycloalkanes is presented, by microwave-assisted ring closure of ω-arylaminonitriles promoted by polyphosphoric acid (PPA) esters. 1-Aryl-2-iminopyrrolidines were easily pre
- Díaz, Jimena E.,Mollo, María C.,Orelli, Liliana R.
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supporting information
p. 2026 - 2031
(2016/10/05)
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- Synthesis and the 5-HT6 receptor antagonistic effect of 3-arylsulfonylamino-5,6-dihydro-6-substituted pyrazolo[3,4]pyridinones for neuropathic pain treatment
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A novel series of 3-arylsulfonylamino-5,6-dihydro-6-substituted-1H- pyrazolo[3,4-c]pyridine-7-ones was designed and synthesized as 5-HT6 ligands. Among the derivatives synthesized, the lead compound, 12b, having piperidine functionality at the 6-position and (1-naphthyl)sulfonamino at the 3-position of the core structure showed the most potent 5-HT6 inhibitory activity in vitro, good stability without CYP liability, and good neuropathic pain alleviation activity in a rat animal model.
- Devegowda, Vani Nelamane,Hong, Jin-Ri,Cho, Sungjin,Lim, Eun Jeong,Choo, Hyunah,Keum, Gyochang,Rhim, Hyewon,Nam, Ghilsoo
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p. 4696 - 4700
(2013/08/23)
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- Synthesis of 1,6-disubstituted 4,5,6,7-tetrahydropyrazolo[3,4-c]pyridin-7- one derivatives and evaluation of their anticancer activity
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Promising anticancer compounds of the type 1,6-disubstituted 4,5,6,7-tetrahydropyrazolo[3,4-c]pyridin-7-ones were identified. The target compounds were readily synthesized in a large scale via a sequence of reactions starting from the commercially available primary amines. Their in vitro anti-proliferative activity has been evaluated on prostate (DU-145), colon (HT-29 and HCT-116) and melanoma (A375P) human cancer cell lines. The relationships between the structure and the anticancer activity, covering all tested cancer cell lines, revealed that the compound 5c with 2,4-dimethylphenyl substituent at R2 was the most potent with the IC50 values in the range as low as 0.16 to 0.40 μM.
- Devegowda, Vani Nelamane,Seo, Seon Hee,Pae, Ae Nim,Nam, Ghilsoo,Choi, Kyung Il
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scheme or table
p. 647 - 650
(2012/05/04)
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- NOVEL 1,6-DISUBSTITUTED-3-AMINO-4,5,6,7-TETRAHYDRO-1H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE COMPOUNDS AND PREPARATION THEREOF
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Provided are a novel 1,6-disubstituted-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-7-one compound, a pharmaceutically acceptable salt compound thereof, a method for preparing the compound, and an anticancer pharmaceutical composition including the compound as an effective ingredient.
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Page/Page column 4-5
(2012/01/13)
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- 1,n-diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
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In the present Letter we report the use of N-arylputrescines as synthetic intermediates for the preparation of N-acyl-N′-aryltetramethylenediamines 3 and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO
- Díaz, Jimena E.,Bisceglia, Juan á.,Mollo, Ma. Cruz,Orelli, Liliana R.
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supporting information; experimental part
p. 1895 - 1897
(2011/04/25)
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- An efficient synthesis of N-arylputrescines and cadaverines
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We present a two-step, general synthesis of N-aryl-putrescines and cadaverines, by cesium carbonate mediated alkylation of anilines with ω-chloronitriles and subsequent reduction. The cesium-mediated alkylation shows remarkable selectivity towards the mon
- Link, Natalia P.,Díaz, Jimena E.,Orelli, Liliana R.
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experimental part
p. 751 - 754
(2009/07/18)
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