Synthesis of phosphaisocoumarin amidates via DIBAL-H-mediated selective amidation of phosphaisocoumarin esters

Org Biomol Chem. 2014 Aug 7;12(29):5458-63. doi: 10.1039/c4ob00663a.

Abstract

A series of phosphaisocoumarin amidates were synthesized for the first time via DIBAL-H-mediated direct amidation of phosphaisocoumarin esters under mild conditions in good to excellent yields. The present reaction showed high selectivity. In each case, the phostone ring was intact and only the exocyclic ethoxy group was amidated. A plausible mechanism of the reaction was provided.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amines / chemistry
  • Esters / chemistry*
  • Isocoumarins / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Organometallic Compounds / chemistry*
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry

Substances

  • Amides
  • Amines
  • Esters
  • Isocoumarins
  • Organometallic Compounds
  • Organophosphonates
  • diisobutylaluminum