Vertaisarvioitu alkuperäisartikkeli tai data-artikkeli tieteellisessä aikakauslehdessä (A1)
Nucleophilic Substitution of Hydrogen Facilitated by Quinone Methide Moieties in Benzo[cd]azulen-3-ones
Julkaisun tekijät: Alexandros Kiriazis, Ingo B. Aumüller, Ralica Arnaudova, Vanessa Brito, Tobias Rüffer, Heinrich Lang, Samuel M. Silvestre, Päivi J. Koskinen, Jari Yli-Kauhaluoma
Kustantaja: AMER CHEMICAL SOC
Julkaisuvuosi: 2017
Journal: Organic Letters
Tietokannassa oleva lehden nimi: ORGANIC LETTERS
Lehden akronyymi: ORG LETT
Volyymi: 19
Julkaisunumero: 8
Aloitussivu: 2030
Lopetussivun numero: 2033
Sivujen määrä: 4
ISSN: 1523-7060
eISSN: 1523-7052
DOI: http://dx.doi.org/10.1021/acs.orglett.7b00588
Tiivistelmä
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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