Organocatalytic aza-Michael Reaction to 3-Vinyl-1,2,4-triazines as a Valuable Bifunctional Platform

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

1 ICOA - Institut de Chimie Organique et Analytique
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

An unprecedented catalytic aza-Michael addition to substituted 3-vinyl-1,2,4-triazines, as original bifunctional platforms for the domino conjugate addition inverse-electron-demand hetero-Diels–Alder/retro-Diels–Alder (ihDA/rDA) reaction, was achieved using the highly acidic triflimide as an organocatalyst. Based on the use of alkoxyamine nucleophiles, this sequence not only highlights a rare example of the catalytic aza-Michael reaction to alkenylazaarenes but also proves to be useful for the elaboration of an array of biorelevant tetrahydro-[1,6]-naphthyridines.

Domains: Organic chemistry; Catalysis

Floris Buttard, Clément Berthonneau, Marie-Aude Hiebel, Jean-François Brière, Franck Suzenet. Organocatalytic aza-Michael Reaction to 3-Vinyl-1,2,4-triazines as a Valuable Bifunctional Platform. Journal of Organic Chemistry, 2019, 84 (6), pp.3702-3714. ⟨10.1021/acs.joc.9b00141⟩. ⟨hal-02197289⟩