Chemodivergent reaction of azomethine imines and 2H-azirines for the synthesis of nitrogen-containing scaffolds. Issue 22 (22nd May 2019)

• Record Type: Journal Article
• Authors: Wu, Yufeng; Tian, Bing; Hu, Chao; Sekine, Kohei; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 22(2019)
• Page Start: 5505
• Page End: 5508
• Publication Date: 2019-05-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00740g
• Languages: English
• ISSNs: 1477-0520

Abstract

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