Nucleophilic Substitution of Hydrogen Facilitated by Quinone Methide Moieties in Benzo[cd]azulen-3-ones

This is the authors' abstract. We don't add key points for this paper.

The built-in o - and p -QM (QM = quinone methide) moieties in benzo[ cd ]azulen-3-ones account for an easy switch between the bridged 10π- and 6π-aromatic systems in organic synthesis. We report conjugate additions, oxidative nucleophilic substitutions of hydrogen, and reversible Michael additions under very mild conditions. In the presence of thiol nucleophiles, the protonated σ H -adducts could be isolated and characterized. The typical preference for either the o - or p -QM moiety led to high regioselectivity. Furthermore, the inhibitory potency of the novel benzo[ cd ]azulenes against the human Pim-1 kinase was evaluated.