2. Academic Validation
  3. Methylene Blue as a Photosensitizer and Redox Agent: Synthesis of 5-Hydroxy-1H-pyrrol-2(5H)-ones from Furans

Methylene Blue as a Photosensitizer and Redox Agent: Synthesis of 5-Hydroxy-1H-pyrrol-2(5H)-ones from Furans

  • Angew Chem Int Ed Engl. 2015 May 18;54(21):6283-7. doi: 10.1002/anie.201500744.
Dimitris Kalaitzakis 1,  Antonia Kouridaki 1,  Dimitris Noutsias 1,  Tamsyn Montagnon 1,  Georgios Vassilikogiannakis 2
Affiliations

Affiliations

  • 1 Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete (Greece) http://www.chemistry.uoc.gr/vassilikogiannakis.
  • 2 Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete (Greece) http://www.chemistry.uoc.gr/vassilikogiannakis. vasil@chemistry.uoc.gr.
PMID: 25865698 DOI: 10.1002/anie.201500744
Abstract

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.

Keywords

furan oxidation; methylene blue; singlet oxygen; sustainable chemistry; α,β-unsaturated γ-lactams.

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