Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling.
作者： James J. Perkins , Alayna M. Johnson , Valerie W. Shurtleff , Abdellatif El Marrouni
DOI: 10.1021/ACSMEDCHEMLETT.0C00673
关键词: Late stage 、 Purine 、 Alkyl 、 Nickel 、 Combinatorial chemistry 、 Catalysis 、 Nucleoside 、 Drug discovery 、 Chemistry
摘要: … For convenience and consistency of the ligand-to-metal-ratio, we employed the preligated complex [Ni(dtbbpy)(H 2 O) 4 ]Cl 2 reported by Molander and co-workers as our source of …
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sci-hub.st 参考文章(42)
Gui-Rong Qu, Zhi-Jie Mao, Hong-Ying Niu, Dong-Chao Wang, Chao Xia, Hai-Ming Guo, Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate. Organic Letters. ,vol. 11, pp. 1745- 1748 ,(2009) , 10.1021/OL9002256
Robert J. Perkins, Alexander J. Hughes, Daniel J. Weix, Eric C. Hansen, Metal-Reductant-Free Electrochemical Nickel-CatalyzedCouplings of Aryl and Alkyl Bromides in Acetonitrile Organic Process Research & Development. ,vol. 23, pp. 1746- 1751 ,(2019) , 10.1021/ACS.OPRD.9B00232
Qingfeng Li, Leentje Persoons, Dirk Daelemans, Piet Herdewijn, Iron/Copper Co-Catalyzed Cross-Coupling Reaction for the Synthesis of 6-Substituted 7-Deazapurines and the Corresponding Nucleosides. Journal of Organic Chemistry. ,vol. 85, pp. 403- 418 ,(2020) , 10.1021/ACS.JOC.9B02414
Blaise L. Truesdell, Taylor B. Hamby, Christo S. Sevov, General C(sp2)-C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts. Journal of the American Chemical Society. ,vol. 142, pp. 5884- 5893 ,(2020) , 10.1021/JACS.0C01475
Alexander Dömling, Li Gao, Chemistry and Biology of SARS-CoV-2 Chem. ,vol. 6, pp. 1283- 1295 ,(2020) , 10.1016/J.CHEMPR.2020.04.023
Daniel A. Everson, Brittany A. Jones, Daniel J. Weix, Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides Journal of the American Chemical Society. ,vol. 134, pp. 6146- 6159 ,(2012) , 10.1021/JA301769R
Hai-Ming Guo, Yu Zhang, Hong-Ying Niu, Dong-Chao Wang, Zhi-Liang Chu, Gui-Rong Qu, Microwave promoted C6-alkylation of purines through SNAr-based reaction of 6-chloropurines with 3-alkyl-acetylacetone Organic and Biomolecular Chemistry. ,vol. 9, pp. 2065- 2068 ,(2011) , 10.1039/C0OB01213K
Peiyuan Wang, Byoung-Kwon Chun, Suguna Rachakonda, Jinfa Du, Noshena Khan, Junxing Shi, Wojciech Stec, Darryl Cleary, Bruce S. Ross, Michael J. Sofia, An efficient and diastereoselective synthesis of PSI-6130: a clinically efficacious inhibitor of HCV NS5B polymerase. Journal of Organic Chemistry. ,vol. 74, pp. 6819- 6824 ,(2009) , 10.1021/JO901345J
Joe Liu, Daniel Obando, Vivian Liao, Tulip Lifa, Rachel Codd, The many faces of the adamantyl group in drug design European Journal of Medicinal Chemistry. ,vol. 46, pp. 1949- 1963 ,(2011) , 10.1016/J.EJMECH.2011.01.047
Ran Xia, Ming-Sheng Xie, Hong-Ying Niu, Gui-Rong Qu, Hai-Ming Guo, Radical route for the alkylation of purine nucleosides at C6 via Minisci reaction. Organic Letters. ,vol. 16, pp. 444- 447 ,(2014) , 10.1021/OL4033336