Solvent-free synthesis of novel steroidal 2-aminopyridines

Steroids. 2016 Nov:115:147-153. doi: 10.1016/j.steroids.2016.09.005. Epub 2016 Sep 14.

Abstract

The synthesis of novel steroidal 3-cyano-2-aminopyridines using enaminonitrile and various primary amines was established under solvent-free condition. Structures of the new compounds were characterized by MS, 1H and 13C NMR data and the structure of 2-aminopyridine of the product 5b was further confirmed by X-ray analysis. The reaction mechanism was proposed on the basis of the key intermediate obtained. The adjacent amine and nitrile groups existed in the final products have the potential for late stage functionalization, which would provide efficient access to steroidal compound collections with structural diversity and complexity.

Keywords: Enaminonitrile; Solvent-free; Steroidal pyridines; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminopyridines / chemical synthesis*
  • Aminopyridines / chemistry*
  • Crystallography, X-Ray
  • Heterocyclic Compounds, 2-Ring / chemical synthesis
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Molecular Structure
  • Nitriles / chemical synthesis
  • Nitriles / chemistry
  • Solvents / chemistry*
  • Steroids / chemical synthesis*
  • Steroids / chemistry*

Substances

  • Aminopyridines
  • Heterocyclic Compounds, 2-Ring
  • Nitriles
  • Solvents
  • Steroids
  • enaminonitrile
  • alpha-aminopyridine