Abstract
The metal-free reactions of 2H-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.
| Original language | English |
|---|---|
| Pages (from-to) | 5505-5508 |
| Number of pages | 4 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 17 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - Jan 1 2019 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Chemodivergent reaction of azomethine imines and 2 : H -azirines for the synthesis of nitrogen-containing scaffolds. / Wu, Yufeng; Tian, Bing; Hu, Chao; Sekine, Kohei; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.
In: Organic and Biomolecular Chemistry, Vol. 17, No. 22, 01.01.2019, p. 5505-5508.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chemodivergent reaction of azomethine imines and 2
T2 - H -azirines for the synthesis of nitrogen-containing scaffolds
AU - Wu, Yufeng
AU - Tian, Bing
AU - Hu, Chao
AU - Sekine, Kohei
AU - Rudolph, Matthias
AU - Rominger, Frank
AU - Hashmi, A. Stephen K.
PY - 2019/1/1
Y1 - 2019/1/1
N2 - The metal-free reactions of 2H-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.
AB - The metal-free reactions of 2H-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.
UR - http://www.scopus.com/inward/record.url?scp=85066929124&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85066929124&partnerID=8YFLogxK
U2 - 10.1039/c9ob00740g
DO - 10.1039/c9ob00740g
M3 - Article
C2 - 31115432
AN - SCOPUS:85066929124
VL - 17
SP - 5505
EP - 5508
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 22
ER -