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

Abstract

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.

Synthesis and Photophysical Characterization of a pH‐Sensitive Quadracyclic Uridine (qU) Analogue

“…This is in line with literature precedence of haloselectivity on the isoquinoline ring, in which position 1 reacts much faster than position 3 (Figure 2). [27] Next, the tetracyclic fused heterocycle 4 was obtained through a 2‐step, 1‐pot process involving diazotization and copper‐catalyzed intramolecular cyclization, known as a Pschorr reaction [28] . The conversion of amine 2 to the corresponding diazonium salt 3 was straightforward with above 95 % conversion.…”