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Copper-assisted synthesis of dihydropyrano[2.3-b]indole-4-ones by domino cascade reaction
Yang Luo1, Xue Zhong, Jiang-Kun Huang
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan 610041, P. R. China. heling2012@scu.edu.cn.
Abstract:
A novel copper-catalyzed cascade intermolecular and intramolecular oxidation/cyclization domino one-pot reaction process for the regioselective synthesis of dihydropyrano[2.3-b]indol-4(9H)-ones has been successfully developed. In this methodology, it is proposed for the first time that the 4-benzyloxy group of indole substrates can be used as a guiding group to promote cyclization under mild conditions. Meanwhile, reaction mechanism studies indicate that carbonyl oxygen in pyranoindole-4-ones came from water and the guiding group is critical to the progress of the reaction.
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