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- Title
Activation/Cyclization of 2H‐Azirines and 3‐Amino‐2‐fluoropyridines Towards 2‐Aryl‐Pyrido[2,3‐b]pyrazines.
- Authors
Fortier, Tess; Belouin, Audrey; Vuillermet, Frédéric; Bourret, Joanick; Pelletier, Guillaume
- Abstract
The electrophilic activation of 2H‐azirines with triflic anhydride (Tf2O) for an addition/cyclization reaction producing 2‐aryl‐pyrido[2,3‐b]pyrazines regioselectively is described. This reaction proceeds via nucleophilic addition of 3‐amino‐2‐fluoropyridines onto 1‐trifloyl‐aziridin‐2‐yl triflates and subsequent cyclization via SNAr. Desulfonylation and oxidation provides a single regioisomer of the aza‐bicyclic heterocycle after treatment with Et3N. Optimization of the reaction conditions lead to a range of 2‐aryl‐pyrido[2,3‐b]pyrazines in isolated yields of 20 % to 60 %.
- Subjects
RING formation (Chemistry); PYRAZINES; OXIDATION; PYRIDINE
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 24, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400297