Ru(II)-Catalyzed C-H Amidation of Indoline at the C7-Position Using Dioxazolone as an Amidating Agent: Synthesis of 7-Amino Indoline Scaffold

J Org Chem. 2017 Dec 15;82(24):13405-13413. doi: 10.1021/acs.joc.7b02500. Epub 2017 Nov 28.

Abstract

The Ru(II)-catalyzed C-H amidation of indoline at the C7-position en route for synthesizing the 7-amino indole scaffold has been achieved by using dioxazolone, which is an environmentally benign amidating reagent. This protocol paves the way for synthesizing a variety of 7-amino indole derivatives in excellent yields at ambient reaction conditions. The readily cleavable amide group has been utilized as a directing group for the amidation. The derivatives of 7-amino indole are synthetically useful for accessing a variety of natural products, drug molecules, and biologically active compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Ruthenium / chemistry*

Substances

  • Amides
  • Indoles
  • indoline
  • Ruthenium