Chemodivergent reaction of azomethine imines and 2H-azirines for the synthesis of nitrogen-containing scaffolds
Metal-free reactions of 2-H-azirines with C-, N-cyclic azomethine imines were investigated. The metal-free reactions of 2-H-azirines with C-, N-cyclic azomethine imines were investigated. N-Bridged strained ring-fused triazole derivatives or 1,2,4-triazine derivatives are obtained, and the chemosele...
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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
10 May 2019
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| In: |
Organic & biomolecular chemistry
Year: 2019, Volume: 17, Issue: 22, Pages: 5505-5508 |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/C9OB00740G |
| Online Access: | Verlag, Volltext: https://doi.org/10.1039/C9OB00740G Verlag: http://xlink.rsc.org/?DOI=C9OB00740G 
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| Author Notes: | Yufeng Wu, Bing Tian, Chao Hu, Kohei Sekine, Matthias Rudolph, Frank Rominger and A. Stephen K. Hashmi |
| Summary: | Metal-free reactions of 2-H-azirines with C-, N-cyclic azomethine imines were investigated. The metal-free reactions of 2-H-azirines with C-, N-cyclic azomethine imines were investigated. N-Bridged strained ring-fused triazole derivatives or 1,2,4-triazine derivatives are obtained, and the chemoselectivity is dependent on the protecting group on the azomethine dipole. Although benzoyl-protected starting materials give access to strained polycyclic compounds, a ring-opening occurs in the case of a tosyl protecting group that is cleaved during the process with elimination of sulfinic acid. 1,2,4-Triazine can be prepared on a mmol-scale and concomitantly oxidized with air as an oxidant to form the corresponding ketone, which is an interesting structural motif that can be found in bioactive scaffolds. |
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| Item Description: | Gesehen am 21.10.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/C9OB00740G |