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

Yufeng Wu, Bing Tian, Chao Hu, Kohei Sekine, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi

研究成果: ジャーナルへの寄稿記事

抜粋

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.

元の言語英語
ページ(範囲)5505-5508
ページ数4
ジャーナルOrganic and Biomolecular Chemistry
17
発行部数22
DOI
出版物ステータス出版済み - 1 1 2019
外部発表Yes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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