Site-Selective Synthesis of Antitumor C5-Aminated Indoles via Neighboring Aldehyde Group Assisted Catellani Reaction
Guangyuan Liu1, Mengzhu Zheng1, Rong Tian2
1Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
Abstract:
A palladium/norbornene (NBE) cooperative catalytic system was developed to access C5-aminated indoles, starting from readily available C4-idonated indoles. Good yields and exclusive site selectivity were achieved for a broad substrate scope, including drug molecule core architectures. Control experiments found that both aldehyde on the C3 position and sulfonyl protecting group on the N1 position were vital for the transformation. Preliminary bioactivity evaluation identified a promising leading compound 3af with potent antitumor proliferative activity against several cancer cells.
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