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
  • 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. [email protected].
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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