Sequential Michael Addition and Enamine-Promoted Inverse Electron Demanding Diels–Alder Reaction upon 3-Vinyl-1,2,4-triazine Platforms

Magali Lorion (1) , Gerald Guillaumet (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 original one-pot Michael addition-ihDA/rDA sequence was achieved from 3-vinyl-1,2,4-triazine platforms used as unprecedented Michael acceptors. This sequence provides a novel access to functionalized [2,3]-fused pyridine derivatives via a unique enamine promoted intramolecular ihDA reaction of 1,2,4-triazine intermediates.

Domaines: Chimie organique; Catalyse

Magali Lorion, Gerald Guillaumet, Jean-François Brière, Franck Suzenet. Sequential Michael Addition and Enamine-Promoted Inverse Electron Demanding Diels–Alder Reaction upon 3-Vinyl-1,2,4-triazine Platforms. Organic Letters, 2015, 17 (12), pp.3154-3157. ⟨10.1021/acs.orglett.5b01487⟩. ⟨hal-01167194⟩