Gold(I)-Catalyzed Pathway-Switchable Syntheses of Azocine[4,5-b]indole and (1H-indol-3-yl)-Azepino[4,5-b]indole
Jiaji Li1,2, Zhibin Zhao1,3,2, Ziqiang Xu1,3,2
1Key Laboratory of Structure-Based Drug Design and Discovery, (Shenyang Pharmaceutical University), Ministry of Education, Shenyang 110016, P. R. China.
Abstract:
A pathway-switchable gold(I)-catalyzed N-propargyl tryptamine cycloisomerization strategy was developed and successfully used for the syntheses of azocine[4,5-b]indole and (1H-indol-3-yl)-azepino[4,5-b]indole derivatives. The optimal reaction conditions for the two pathways were determined through detailed studies, and the scope of this pathway-switchable approach was explored using a series of N-propargyl tryptamine substrates. A gold(I)-catalyzed 8-endo-dig or 7-exo-dig cycloisomerization mechanism regulated by substituents and nucleophiles was proposed.
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