Carbon protonation of 2, 4, 6-triaminopyrimidines: Synthesis, NMR studies, and theoretical calculations

…, T Veszprémi, T Gáti, Á Demeter

Index: Nemeth, Balazs; Weber, Csaba; Veszpremi, Tamas; Gati, Tamas; Demeter, Adam Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4910 - 4918

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Citation Number: 7

Abstract

Several C (5)-substituted 2, 4, 6-triaminopyrimidine derivatives and their HBF4 salts were synthesized to study the carbon protonation of the pyrimidine ring. NMR investigations in DMSO-d 6 prove experimentally that, in addition to the usual protonation at N (1), the compounds can be protonated at C (5) as well. We present several new stable cationic σ- complexes in the pyrimidine series, where C (5) protonation predominates over N (1) ...