Regioselective Silver‐Catalyzed Carbon‐Phosphorus Difunctionalization of Maleimides: One‐Step Construction of Phosphonylated Indolylmaleimides and Pyrrolylmaleimides
作者： Zhen-Hua Yang , Hong-Ru Tan , Jia-Nan Zhu , Jian Zheng , Sheng-Yin Zhao
关键词:
摘要: An efficient silver-catalyzed intermolecular carbon-phosphorus difunctionalization of maleimides with indoles/pyrroles and organophosphorus compounds including dialkyl phosphites diphenylphosphine oxide was developed. A diverse range phosphonylated indolylmaleimides pyrrolylmaleimides were obtained in good yields excellent regioselectivity, involving C−P C−C bond formations. This methodology is very practical enables a one-step construction difunctionalized maleimides.
sci-hub.se 参考文章(53)
J. M. Bayne, D. W. Stephan, Phosphorus Lewis acids: emerging reactivity and applications in catalysis Chemical Society Reviews. ,vol. 45, pp. 765- 774 ,(2016) , 10.1039/C5CS00516G
Mahipal Yadav, Saidulu Dara, Varma Saikam, Mukesh Kumar, Sravan Kumar Aithagani, Satya Paul, Ram A Vishwakarma, Parvinder Pal Singh, None, Regioselective Oxidative C–H Phosphonation of Imidazo[1,2‐a]pyridines and Related Heteroarenes Mediated by Manganese(III) Acetate European Journal of Organic Chemistry. ,vol. 2015, pp. 6526- 6533 ,(2015) , 10.1002/EJOC.201500984
Sheng-Yin Zhao, Yan-Wu Yang, Hai-Quan Zhang, Yun Yue, Mei Fan, Synthesis and cytotoxicity of novel 3-amino-4-indolylmaleimide derivatives Archives of Pharmacal Research. ,vol. 34, pp. 519- 526 ,(2011) , 10.1007/S12272-011-0401-Z
Barrie J. Marsh, Harry Adams, Mike D. Barker, Ibrahim U. Kutama, Simon Jones, Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: synthesis of (R)-pyrrolam A. Organic Letters. ,vol. 16, pp. 3780- 3783 ,(2014) , 10.1021/OL5016702
Christian Peifer, Agata Krasowski, Nina Hämmerle, Oliver Kohlbacher, Gerd Dannhardt, Frank Totzke, Christoph Schächtele, Stefan Laufer, Profile and Molecular Modeling of 3-(Indole-3-yl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole-2,5dione (1) as a Highly Selective VEGF-R2/3 Inhibitor Journal of Medicinal Chemistry. ,vol. 49, pp. 7549- 7553 ,(2006) , 10.1021/JM0609871
Sudipta Roy, Sujata Roy, Gordon W. Gribble, A Practical Method for the Synthesis of Indolylaryl- and Bisindolylmaleimides Organic Letters. ,vol. 8, pp. 4975- 4977 ,(2006) , 10.1021/OL0621203
Manabu Nakazono, Shinkoh Nanbu, Akihiro Uesaki, Ryoichi Kuwano, Manabu Kashiwabara, Kiyoshi Zaitsu, Bisindolylmaleimides with large Stokes shift and long-lasting chemiluminescence properties. Organic Letters. ,vol. 9, pp. 3583- 3586 ,(2007) , 10.1021/OL701431G
Hendra Gunosewoyo, Andrew Midzak, Irina N. Gaisina, Emily V. Sabath, Allison Fedolak, Taleen Hanania, Dani Brunner, Vassilios Papadopoulos, Alan P. Kozikowski, Characterization of Maleimide-Based Glycogen Synthase Kinase-3 (GSK-3) Inhibitors as Stimulators of Steroidogenesis Journal of Medicinal Chemistry. ,vol. 56, pp. 5115- 5129 ,(2013) , 10.1021/JM400511S
J. P. Haelters, B. Corbel, G. Sturtz, SYNTHESE D'INDOLE PHOSPHONATES PAR CYCLISATION SELON FISCHER D'ARYLHYDRAZONES PHOSPHONATES Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 37, pp. 41- 63 ,(1988) , 10.1080/03086648808074351
Ming-Der Wu, Ming-Jen Cheng, Bor-Cheh Wang, Yi-Jen Yech, Jinn-Tsyy Lai, Yao-Haur Kuo, Gwo-Fang Yuan, Ih-Sheng Chen, Maleimide and maleic anhydride derivatives from the mycelia of Antrodia cinnamomea and their nitric oxide inhibitory activities in macrophages. Journal of Natural Products. ,vol. 71, pp. 1258- 1261 ,(2008) , 10.1021/NP070634K