Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines

Molecules. 2021 Mar 29;26(7):1910. doi: 10.3390/molecules26071910.


N-heteroaryl substituted adamantane-containing amines are of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of N-heterocycles has been substituted by the amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of the second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine, and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis.

Keywords: Pd catalysis; adamantane; amination; amines; isoquinoline; pyrazine; pyrimidine.

MeSH terms

  • Adamantane / chemistry
  • Amination
  • Amines / chemistry*
  • Catalysis
  • Molecular Structure
  • Pyrazines / chemistry


  • 2,6-dichloropyrazine
  • Amines
  • Pyrazines
  • Adamantane