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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)5505-5508
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number22
DOIs
Publication statusPublished - Jan 1 2019

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Azirines
Imines
Scaffolds
imines
Nitrogen
Sulfinic Acids
Polycyclic Compounds
Derivatives
nitrogen
Triazoles
rings
synthesis
activity (biology)
Ketones
Oxidants
ketones
elimination
Metals
Air
dipoles

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 journalArticle

Wu, Yufeng ; Tian, Bing ; Hu, Chao ; Sekine, Kohei ; Rudolph, Matthias ; Rominger, Frank ; Hashmi, A. Stephen K. / Chemodivergent reaction of azomethine imines and 2 : H -azirines for the synthesis of nitrogen-containing scaffolds. In: Organic and Biomolecular Chemistry. 2019 ; Vol. 17, No. 22. pp. 5505-5508.
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