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.
N1 - Funding Information:
Y. Wu, B. Tian, and C. Hu are grateful for a Ph.D. fellowship from the China Scholarship Council (CSC).
Publisher Copyright:
© 2019 The Royal Society of Chemistry.
PY - 2019
Y1 - 2019
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.
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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 -