Refereed journal article or data article (A1)
Nucleophilic Substitution of Hydrogen Facilitated by Quinone Methide Moieties in Benzo[cd]azulen-3-ones
List of Authors: Alexandros Kiriazis, Ingo B. Aumüller, Ralica Arnaudova, Vanessa Brito, Tobias Rüffer, Heinrich Lang, Samuel M. Silvestre, Päivi J. Koskinen, Jari Yli-Kauhaluoma
Publisher: AMER CHEMICAL SOC
Publication year: 2017
Journal: Organic Letters
Journal name in source: ORGANIC LETTERS
Journal acronym: ORG LETT
Volume number: 19
Issue number: 8
Start page: 2030
End page: 2033
Number of pages: 4
ISSN: 1523-7060
eISSN: 1523-7052
DOI: http://dx.doi.org/10.1021/acs.orglett.7b00588
Abstract
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.
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.
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