Refereed journal article or data article (A1)

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

List of AuthorsAlexandros Kiriazis, Ingo B. Aumüller, Ralica Arnaudova, Vanessa Brito, Tobias Rüffer, Heinrich Lang, Samuel M. Silvestre, Päivi J. Koskinen, Jari Yli-Kauhaluoma


Publication year2017

JournalOrganic Letters

Journal name in sourceORGANIC LETTERS

Journal acronymORG LETT

Volume number19

Issue number8

Start page2030

End page2033

Number of pages4




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 10 pi- and 6 pi-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 sigma(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.

Last updated on 2021-24-06 at 09:39