Selective reduction of condensed N-heterocycles using water as a solvent and a hydrogen source

Org Biomol Chem. 2013 Feb 21;11(7):1209-15. doi: 10.1039/c2ob26903a.

Abstract

The reduction of unprotected indoles and quinolines is described using water as a hydrogen source. The method is based on the application of a RANEY® type Ni-Al alloy in an aqueous medium. During the reaction the Al content of the alloy, used as reductants, reacts with water in situ providing hydrogen and a RANEY® Ni catalyst, thus the alloy serves as a hydrogen generator as well as a hydrogenation catalyst. The simplicity and efficacy of the method are illustrated by the selective reduction of a variety of substituted indoles and quinolines to indolines and tetrahydroquinolines, respectively.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrogen / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Solvents / chemistry
  • Water / chemistry*

Substances

  • Heterocyclic Compounds
  • Solvents
  • Water
  • Hydrogen