Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes

J Org Chem. 2013 Feb 1;78(3):1311-6. doi: 10.1021/jo3027033. Epub 2013 Jan 23.

Abstract

A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Cycloparaffins / chemistry*
  • Furans / chemistry*
  • Microwaves
  • Molecular Structure
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / chemistry
  • Stereoisomerism

Substances

  • Aza Compounds
  • Cycloparaffins
  • Furans
  • Phenanthridines