Direct Synthesis of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Diynes
The Journal of Organic Chemistry2011Vol. 76(5), pp. 1212–1227
Citations Over TimeTop 10% of 2011 papers
Kimio Hirano, Yusuke Inaba, N. Takahashi, Masanao Shimano, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno
Abstract
A direct, concise, and atom-economical synthetic method for the generation of fused indoles, using a gold-catalyzed cascade cyclization of diynes, has been developed. The reaction gave various fused indoles, such as aryl-annulated[a]carbazoles, dihydrobenzo[g]indoles, and azepino- or oxepinoindole derivatives in good to excellent yields, through an intramolecular cascade 5-endo-dig hydroamination followed by a 6- or 7-endo-dig cycloisomerization, without producing theoretical byproduct. Three of the resulting indoles exhibited potent antifungal activities against T. mentagrophytes and T. rubrum, demonstrating the practical application of the described cascade reaction for drug discovery.
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