Successive Promotion of Formal [3+2] Cycloaddition of Aryl Methyl Ketones by I2 and Zn: Access to 2-Hydroxy-4-morpholin-2,5-diarylfuran-3(2 H)-ones with a Quaternary Carbon Center

J Org Chem. 2023 Jul 7;88(13):9321-9331. doi: 10.1021/acs.joc.3c00885. Epub 2023 Jun 15.

Abstract

2-Hydroxy-4-morpholin-2,5-diarylfuran-3(2H)-one derivatives were constructed sequentially using iodine and zinc dust from simple and readily available methyl ketone and morpholine as the starting materials. Under mild conditions, C-C, C-N, and C-O bonds formed in a one-pot synthesis. A quaternary carbon center was successfully constructed, and the active drug fragment morpholine was introduced into the molecule.

MeSH terms

  • Acetone
  • Carbon*
  • Cycloaddition Reaction
  • Iodine* / chemistry
  • Ketones / chemistry
  • Morpholines

Substances

  • Carbon
  • Acetone
  • Iodine
  • Morpholines
  • Ketones