Organocatalyzed Thia-Michael Addition and Sequential Inverse Electron Demanding Diels-Alder Reaction to 3-Vinyl-1,2,4- triazine Platforms

Clément Berthonneau (1) , F. Buttard (2) , Marie-Aude Hiebel (2) , Franck Suzenet (2, 3) , Jean-François Brière (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ICOA - Institut de Chimie Organique et Analytique
3 UO - Université d'Orléans

This work highlights the use of 3‐vinyl‐1,2,4‐triazines as original thia‐Michael acceptors and inverse electron demanding Diels‐Alder platforms en route to new 7,8‐dihydro‐5H‐thiopyrano[4,3‐b ]pyridines. The required but rather unstable propargylthiol nucleophiles were successfully generated in‐situ upon an innovative DBU‐catalyzed methanolysis event of the corresponding propargyl thioacetate derivatives.

Domaines: Chimie

Clément Berthonneau, F. Buttard, Marie-Aude Hiebel, Franck Suzenet, Jean-François Brière. Organocatalyzed Thia-Michael Addition and Sequential Inverse Electron Demanding Diels-Alder Reaction to 3-Vinyl-1,2,4- triazine Platforms. Advanced Synthesis and Catalysis, 2017, 359 (23), pp.4106-4110. ⟨10.1002/adsc.201700831⟩. ⟨hal-02046260⟩