Domino Aza-Michael-ih-Diels-Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

Jabrane Jouha (1) , Floris Buttard (1) , Magali Lorion (1) , Clément Berthonneau (2) , Mostafa Khouili , Marie-Aude Hiebel (1) , Gérald Guillaumet (1, 3) , Jean-François Brière (2) , Franck Suzenet (1, 3)

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

A straightforward domino aza-Michael-inverse-electron-demand-hetero-Diels–Alder/retro-Diels–Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-heterocyclic platform but also a novel and unprecedented path to polysubstituted tetrahydro-1,6-naphthyridine scaffolds.

Domains: Chemical Sciences

Jabrane Jouha, Floris Buttard, Magali Lorion, Clément Berthonneau, Mostafa Khouili, et al.. Domino Aza-Michael-ih-Diels-Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines. Organic Letters, 2017, 19 (18), pp.4770-4773. ⟨10.1021/acs.orglett.7b02132⟩. ⟨hal-02046286⟩