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

Alexandros Kiriazis, Ingo B. Aumuller, Ralica Zhorova Arnaudova, Vanessa Brito, Tobias Rüffer, Heinrich Lang, Samuel Silvestre, Päivi J. Koskinen, Jari Tapani Yli-Kauhaluoma

Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

Sammanfattning

The built-in ortho-and para-QM (QM = quinone methide) moieties in benzo[cd]azulen-3-ones account foran 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 σH-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.
Originalspråkengelska
TidskriftOrganic Letters
Volym19
Utgåva8
Sidor (från-till)2030-2033
Antal sidor4
ISSN1523-7060
DOI
StatusPublicerad - 21 apr 2017
MoE-publikationstypA1 Tidskriftsartikel-refererad

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