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Silver-Mediated Cascade Synthesis of Functionalized 1,4-dihydro-2H-Benzo-1,3-Oxazin-2-Ones from Carbon Dioxide.

Xuetong LiJordi Benet-BuchholzEduardo C Escudero-AdánArjan W Kleij
Published in: Angewandte Chemie (International ed. in English) (2023)
A conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4-dihydro-2H-1,3-benzoxazine-2-one derivatives. Key to the chemoselectivity is a proper design of the precursor to override thermodynamically favored parasitic cyclization processes and empower the formation of the desired product through Thorpe-Ingold effects. The synthetic diversity of these CO 2 -based heterocycles is further demonstrated, and the isolation of a reaction intermediate supports an unusual ring-expansion sequence from an α-alkylidene, five-membered cyclic carbonate to a six-membered cyclic carbamate by N-induced isomerization.
Keyphrases
  • carbon dioxide
  • gold nanoparticles
  • high glucose
  • diabetic rats
  • quantum dots
  • drug induced
  • silver nanoparticles
  • mass spectrometry
  • molecularly imprinted
  • high resolution
  • electron transfer