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Methylene Blue as a Photosensitizer and Redox Agent: Synthesis of 5-Hydroxy-1H-pyrrol-2(5H)-ones from Furans. 2015
Dimitris Kalaitzakis, and
Antonia Kouridaki, and
Dimitris Noutsias, and
Tamsyn Montagnon, and
Georgios Vassilikogiannakis
Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete (Greece) http://www.chemistry.uoc.gr/vassilikogiannakis.
A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessible furans into 5-hydroxy-1H-pyrrol-2(5H)-ones has been developed. The methodology was extended to the synthesis of other high-value α,β-unsaturated γ-lactams. This useful set of transformations relies not only on the photosensitizing ability of methylene blue, but also on its redox properties: properties that have until now been virtually ignored in a synthetic context.
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