Water-Promoted Indole Migration of Bis(indol-3-yl)-ynamides Using Zn(OTf)2 as a Lewis Acid Catalyst
Zhanshuai Xiao1, Yin Wei1, Min Shi1
1State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China.
Abstract:
A zinc(II)-catalyzed cycloisomerization of bis(indol-3-yl)-ynamides in the presence of water has been established for constructing carbonyl-containing bisindole derivatives in moderate to good yields with good functional group tolerance and a broad substrate scope. The reaction proceeds through a 7-endo-dig cyclization followed by a pseudo-1,6-indole-migration, which is supported by isotope 18O-labeling experiments. Moreover, large-scale synthesis and further synthetic transformation of the obtained product have been also presented.
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