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Chemodivergent reaction of azomethine imines and 2H-azirines for the synthesis of nitrogen-containing scaffolds

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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.

Graphical abstract: Chemodivergent reaction of azomethine imines and 2H-azirines for the synthesis of nitrogen-containing scaffolds

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Publication details

The article was received on 01 Apr 2019, accepted on 07 May 2019 and first published on 10 May 2019


Article type: Communication
DOI: 10.1039/C9OB00740G
Org. Biomol. Chem., 2019, Advance Article

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    Chemodivergent reaction of azomethine imines and 2H-azirines for the synthesis of nitrogen-containing scaffolds

    Y. Wu, B. Tian, C. Hu, K. Sekine, M. Rudolph, F. Rominger and A. S. K. Hashmi, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00740G

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