Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KOtBu promoted intramolecular C-H arylation

Org Biomol Chem. 2016 Sep 28;14(36):8536-44. doi: 10.1039/c6ob01362g. Epub 2016 Aug 22.

Abstract

A simple, efficient, rapid and transition metal-free methodology has been developed by utilizing vasicine (a natural product), as a catalyst for the synthesis of phenanthridinones and dihydrophenanthridines. The reaction proceeds through intramolecular C-H arylation with aryl halides in the presence of KOtBu as a base under microwave irradiation in sulfolane as a solvent. The reaction proceeds well with various aryl iodides, bromides and more remarkably with less reactive aryl chlorides for 15 minutes, providing the corresponding products in 45-90% yields.

MeSH terms

  • Alkaloids / chemistry*
  • Butanols / chemistry*
  • Microwaves*
  • Molecular Structure
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / chemistry
  • Quinazolines / chemistry*

Substances

  • Alkaloids
  • Butanols
  • Phenanthrenes
  • Phenanthridines
  • Quinazolines
  • vasicine
  • tert-butoxide, potassium
  • phenanthridone