Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

Nina A. Larina, Vladimir Lokshin, Jerome Berthet, Stephanie Delbaere, Gaston Vermeersch, Vladimir Khodorkovsky

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air.

Original languageEnglish
Pages (from-to)8291-8299
Number of pages9
JournalTetrahedron
Volume66
Issue number42
DOIs
StatePublished - 16 Oct 2010
Externally publishedYes

Keywords

  • Acridine
  • Fluorescence
  • Hydrogen bonding
  • Photochromism
  • Quinolin-4(1H)-one

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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