Domino Transformations of 3‐Fluoro‐1,2,4‐Triazine Derivatives towards Spirocyclic and Fused Pyridines - Normandie Université Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2023

Domino Transformations of 3‐Fluoro‐1,2,4‐Triazine Derivatives towards Spirocyclic and Fused Pyridines

Résumé

Abstract A domino S N Ar‐ ih DA/ r DA reaction was developed from rarely exploited 3‐fluoro‐1,2,4‐triazines with bifunctional alkyne tethered nucleophiles to construct various fused non‐aromatic/heteroaromatic bicycles in yields ranging from 56 to 99%, notably within the family of valuable spirooxindole derivatives. In this study, the challenging enantioselective phase‐transfer catalyzed arylation of a sulfonyl‐triazine was also demonstrated with up to 66% ee. In both racemic and asymmetric processes, the nature of the leaving group at C3 was key to successfully achieve these sequences.
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hal-04373094 , version 1 (07-01-2024)

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Anthony Lapray, Thomas Martzel, Marie‐aude Hiebel, Sylvain Oudeyer, Franck Suzenet, et al.. Domino Transformations of 3‐Fluoro‐1,2,4‐Triazine Derivatives towards Spirocyclic and Fused Pyridines. Advanced Synthesis and Catalysis, 2023, ⟨10.1002/adsc.202301307⟩. ⟨hal-04373094⟩
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