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

• Verfasst von: Wu, Yufeng [VerfasserIn]
• Verfasst von: Tian, Bing [VerfasserIn]
• Verfasst von: Hu, Chao [VerfasserIn]
• Verfasst von: Sekine, Kohei [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Chemodivergent reaction of azomethine imines and 2H-azirines for the synthesis of nitrogen-containing scaffolds
• Verf.angabe: Yufeng Wu, Bing Tian, Chao Hu, Kohei Sekine, Matthias Rudolph, Frank Rominger and A. Stephen K. Hashmi
• E-Jahr: 2019
• Jahr: 10 May 2019
• Umfang: 4 S.
• Teil: volume:17
• Teil: year:2019
• Teil: number:22
• Teil: pages:5505-5508
• Teil: extent:4
• Fussnoten: Gesehen am 21.10.2019
• Titel Quelle: Enthalten in: Organic & biomolecular chemistry
• Ort Quelle: Cambridge : Royal Society of Chemistry, 2003
• Jahr Quelle: 2019
• Band/Heft Quelle: 17(2019), 22, Seite 5505-5508
• ISSN Quelle: 1477-0539
• DOI: doi:10.1039/C9OB00740G
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1679249681

Abstract

Metal-free reactions of 2-H-azirines with C-, N-cyclic azomethine imines were investigated. The metal-free reactions of 2-H-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.