Molecules (Mar 2021)

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

  • Alisa D. Kharlamova,
  • Anton S. Abel,
  • Alexei D. Averin,
  • Olga A. Maloshitskaya,
  • Vitaly A. Roznyatovskiy,
  • Evgenii N. Savelyev,
  • Boris S. Orlinson,
  • Ivan A. Novakov,
  • Irina P. Beletskaya

DOI
https://doi.org/10.3390/molecules26071910
Journal volume & issue
Vol. 26, no. 7
p. 1910

Abstract

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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.

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