Abstract

AbstractLow temperature 1H NMR spectra of pteridine dissolved in liquid ammonia, indicate that at −60°C a 1: 1 σ‐adduct is formed by addition of ammonia to the C4‐N3 bond in the pyrimidine ring and that at room temperature a stable 2:1 σ‐adduct is obtained by addition of ammonia to the pyrazine ring. The influence of substituents in the pyrimidine and in the pyrazine ring on adduct formation has been investigated. By reaction of pteridine with 15N‐labelled ammonia it was proved that no ring opening ‐ ring closure mechanism in the formation of the adducts is involved.

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