One-pot cascade synthesis of N-methoxyisoquinolinediones via Rh(III)-catalyzed carbenoid insertion C-H activation/cyclization

Chem Commun (Camb). 2015 Jan 14;51(4):668-71. doi: 10.1039/c4cc08407a.

Abstract

Here a new, mild and versatile method for one-pot cascade synthesis of diverse N-methoxyisoquinolinediones via Rh(III)-catalyzed regioselective carbenoid insertion C-H activation/cyclization of N-methoxybenzamides with α-diazotized Meldrum's acid has been achieved. Extension of the developed Rh(III) catalysis for building new analogs of the marketed drug Edaravone has also been demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides / chemistry
  • Catalysis
  • Cyclization
  • Dioxanes / chemistry
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Benzamides
  • Dioxanes
  • Isoquinolines
  • Meldrum's acid
  • Rhodium
  • 3-methoxybenzamide