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: Contribution to journalArticle査読

9 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)5505-5508
ページ数4
ジャーナルOrganic and Biomolecular Chemistry
17
22
DOI
出版ステータス出版済み - 2019
外部発表はい

All Science Journal Classification (ASJC) codes

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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