Access to indole-fused benzannulated medium-sized rings through a gold(I)-catalyzed cascade cyclization of azido-alkynes
Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chemistry can play an important role in solving t...
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| Hauptverfasser: | , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
10 June 2021
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| In: |
Chemistry - a European journal
Year: 2021, Jahrgang: 27, Heft: 51, Pages: 12992-12997 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202101824 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.202101824 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202101824 
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| Verfasserangaben: | Luca C. Greiner, Shinsuke Inuki, Norihito Arichi, Shinya Oishi, Rikito Suzuki, Tomohiro Iwai, Masaya Sawamura, A. Stephen K. Hashmi, and Hiroaki Ohno |
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| 520 | |a Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chemistry can play an important role in solving the difficulty in the formation of medium-sized rings. Namely, phenylene-tethered azido-alkynes undergo arylative cyclization through the formation of a gold carbene intermediate to afford benzannulated indole-fused medium-sized tetracycles. The reactions allow a range of different aryl substitution patterns and efficient access to these otherwise difficult-to-obtain medium-sized rings. This study also demonstrates the feasibility of the semihollow-shaped C-dtbm ligand for the construction of a nine-membered ring. | ||
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| 650 | 4 | |a arylation | |
| 650 | 4 | |a gold catalysis | |
| 650 | 4 | |a heterocycles | |
| 650 | 4 | |a medium-sized rings | |
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