Metal free C-H functionalization of diazines and related heteroarenes with organoboron species and its application in the synthesis of a CDK inhibitor, meriolin 1.
作者： Thanusha Thatikonda , Umed Singh , Srinivas Ambala , Ram A. Vishwakarma , Parvinder Pal Singh
DOI: 10.1039/C6OB00526H
关键词:
摘要: Here, we report a metal-free cross-coupling reaction of diazines and related heteroarenes with organoboron species via C–H functionalization. The optimized conditions represent method for the activation aryl/heteroarylboronic acids, which undergo coupling heteroarenes. Optimized also find application in synthesis pyrimidine-based potent CDK inhibitor, meriolin1.
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Maddali L. N. Rao, Ritesh J. Dhanorkar, Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines European Journal of Organic Chemistry. ,vol. 2014, pp. 5214- 5228 ,(2014) , 10.1002/EJOC.201402455
Luis Bering, Andrey P. Antonchick, Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids Organic Letters. ,vol. 17, pp. 3134- 3137 ,(2015) , 10.1021/ACS.ORGLETT.5B01456
Jennifer M. Schomaker, Thomas J. Delia, Arylation of halogenated pyrimidines via a Suzuki coupling reaction. Journal of Organic Chemistry. ,vol. 66, pp. 7125- 7128 ,(2001) , 10.1021/JO010573+
Masamichi Watanabe, Haruo Koike, Teruyuki Ishiba, Tetsuo Okada, Shujiro Seo, Kentaro Hirai, Synthesis and Biological Activity of Methanesulfonamide Pyrimidine- and N-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-heptenoates, a Novel Series of HMG-CoA Reductase Inhibitors Bioorganic & Medicinal Chemistry. ,vol. 5, pp. 437- 444 ,(1997) , 10.1016/S0968-0896(96)00248-9
Dong-Hwan Lee, Minkee Choi, Byung-Woo Yu, Ryong Ryoo, Abu Taher, Shahin Hossain, Myung-Jong Jin, Expanded Heterogeneous Suzuki–Miyaura Coupling Reactions of Aryl and Heteroaryl Chlorides under Mild Conditions Advanced Synthesis & Catalysis. ,vol. 351, pp. 2912- 2920 ,(2009) , 10.1002/ADSC.200900495
Scott R. Walker, Erin J. Carter, Belinda C. Huff, Jonathan C. Morris, Variolins and related alkaloids Chemical Reviews. ,vol. 109, pp. 3080- 3098 ,(2009) , 10.1021/CR900032S
Eugen Merkul, Elisabeth Schäfer, Thomas J. J. Müller, Rapid synthesis of bis(hetero)aryls by one-pot Masuda borylation-Suzuki coupling sequence and its application to concise total syntheses of meridianins A and G. Organic and Biomolecular Chemistry. ,vol. 9, pp. 3139- 3141 ,(2011) , 10.1039/C1OB05310H
Aude Echalier, Karima Bettayeb, Yoan Ferandin, Olivier Lozach, Monique Clément, Annie Valette, François Liger, Bernard Marquet, Jonathan C. Morris, Jane A. Endicott, Benoît Joseph, Laurent Meijer, Meriolins (3-(pyrimidin-4-yl)-7-azaindoles): synthesis, kinase inhibitory activity, cellular effects, and structure of a CDK2/cyclin A/meriolin complex. Journal of Medicinal Chemistry. ,vol. 51, pp. 737- 751 ,(2008) , 10.1021/JM700940H
E. Vismara, F. Fontana, F. Minisci, A NEW PROCEDURE FOR THE SELECTIVE α-OXYALKYLATION OF HETEROAROMATIC BASES BY CYCLIC ETHERS AND HYDROGEN PEROXIDE Organic Preparations and Procedures International. ,vol. 20, pp. 105- 108 ,(1988) , 10.1080/00304948809355796
Jian Wang, Shan Wang, Gao Wang, Ji Zhang, Xiao-Qi Yu, None, Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway. Chemical Communications. ,vol. 48, pp. 11769- 11771 ,(2012) , 10.1039/C2CC35468C