Ru(II)-Catalyzed C–H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes
作者： Jin Ho Choi , Kunyoung Kim , Harin Oh , Sangil Han , Neeraj Kumar Mishra
DOI: 10.1039/D0OB01663B
关键词:
摘要: The ruthenium(ii)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. This method enables the site-selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various tetracyclic isoindoloquinazolinones by using Cu(OAc)2 as an external oxidant via C-H addition subsequent intramolecular cyclization. A wide substrate scope high level of chemoselectivity well broad functional group tolerance are observed.
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sci-hub.st 参考文章(47)
Fouad H. Darras, Sarah Wehle, Guozheng Huang, Christoph A. Sotriffer, Michael Decker, Amine substitution of quinazolinones leads to selective nanomolar AChE inhibitors with 'inverted' binding mode. Bioorganic & Medicinal Chemistry. ,vol. 22, pp. 4867- 4881 ,(2014) , 10.1016/J.BMC.2014.06.045
Joanna Wencel-Delord, Frank Glorius, C-H bond activation enables the rapid construction and late-stage diversification of functional molecules Nature Chemistry. ,vol. 5, pp. 369- 375 ,(2013) , 10.1038/NCHEM.1607
Xiu Liu, Aimin Qiu, Donald T. Sawyer, The bis(bipyridine)copper(II)-induced activation of dioxygen for the catalytic dehydrogenation of alcohols Journal of the American Chemical Society. ,vol. 115, pp. 3239- 3243 ,(1993) , 10.1021/JA00061A023
Yi Ju, Feng Liu, Chaozhong Li, Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives Organic Letters. ,vol. 11, pp. 3582- 3585 ,(2009) , 10.1021/OL901305Q
Lei Yang, Hanmin Huang, Transition-Metal-Catalyzed Direct Addition of Unactivated C–H Bonds to Polar Unsaturated Bonds Chemical Reviews. ,vol. 115, pp. 3468- 3517 ,(2015) , 10.1021/CR500610P
Liron Feldberg, Yoel Sasson, Copper-catalysed oxidation of hydroxy compounds by tert-butyl hydroperoxide under phase-transfer conditions Journal of The Chemical Society, Chemical Communications. pp. 1807- 1807 ,(1994) , 10.1039/C39940001807
I. E. Marko, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch, Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternative Science. ,vol. 274, pp. 2044- 2046 ,(1996) , 10.1126/SCIENCE.274.5295.2044
Aurore Servais, Mériam Azzouz, David Lopes, Christine Courillon, Max Malacria, Radical cyclization of N-acylcyanamides: total synthesis of luotonin A. Angewandte Chemie. ,vol. 46, pp. 576- 579 ,(2007) , 10.1002/ANIE.200602940
Junichiro Yamaguchi, Atsushi D. Yamaguchi, Kenichiro Itami, C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals Angewandte Chemie. ,vol. 51, pp. 8960- 9009 ,(2012) , 10.1002/ANIE.201201666
Chaoren Shen, Nikki Y. T. Man, Scott Stewart, Xiao-Feng Wu, Palladium-catalyzed dicarbonylative synthesis of tetracycle quinazolinones Organic and Biomolecular Chemistry. ,vol. 13, pp. 4422- 4425 ,(2015) , 10.1039/C5OB00368G