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Rhodium(III)‐Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds |
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| Authors: | Miho Fukui Dr Yu Shibata Yuki Hoshino Haruki Sugiyama Kota Teraoka Prof?Dr Hidehiro Uekusa Prof?Dr Keiichi Noguchi Prof?Dr Ken Tanaka |
| Institution: | 1. http://www.tuat.ac.jp/～tanaka‐k/;2. Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan;3. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, Japan;4. Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan;5. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo, Japan |
| Abstract: | An electron‐deficient CpE rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem 2+2+2] annulation–lactamization of acetanilides with two alkynoates via cleavage of adjacent two C?H bonds to give densely substituted benzocd]indolones. The reactions of meta‐methoxy‐substituted acetanilides with two alkynoates also provided benzocd]indolones via cleavage of adjacent C?H/C?O bonds. Furthermore, 3,5‐dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds. |
| Keywords: | alkynes anilides annulation benzo[cd]indolones rhodium |