Molecular Transformation to Pyrroles,Pentafulvenes, and Pyrrolopyridines by [2+2] Cycloaddition of Propargylamines with Tetracyanoethylene |
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| Authors: | Prof?Dr Taku Shoji Sho Takagaki Yukino Ariga Akari Yamazaki Mutsumi Takeuchi Prof?Dr Akira Ohta Dr Ryuta Sekiguchi Dr Shigeki Mori Prof?Dr Tetsuo Okujima Prof?Dr Shunji Ito |
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| Institution: | 1. Department of Material Science, Graduate School of, Science and Technology, Shinshu University, Matsumoto, 390-8621 Nagano, Japan;2. Advanced Research Support Center, Ehime University, Matsuyama, 790-8577 Ehime, Japan;3. Department of Chemistry and Biology, Graduate School of, Science and Engineering, Ehime University, Matsuyama, 790-8577 Ehime, Japan;4. Graduate School of Science and Technology, Hirosaki University, Hirosaki, 036-8561 Aomori, Japan |
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| Abstract: | In this paper, we describe an efficient and atom-economical synthesis of highly functionalized pyrroles, pentafulvenes, and pyrrolopyridines by 2+2] cycloaddition–retroelectrocyclization of N-substituted propargylamines with tetracyanoethylene, followed by the treatment of the resulting tetracyanobutadiene derivatives with silica gel. In this reaction, silica gel plays an important role to promote the intramolecular cyclization to afford the heterocyclic products from the tetracyanobutadiene intermediates. The products were obtained selectively depending on the substituent on the nitrogen atom of the starting propargylamines. |
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| Keywords: | cycloaddition intramolecular cyclization pentafulvenes pyrroles pyrrolopyridines |
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