Synthesis of heterofunctional 1,3,7-triazapyrene derivatives by SNH and SNAr reactions

Abstract

1,3,7-Triazapyrene reacts with amino alcohols in aqueous medium in the presence of K3Fe(CN)6 or in the system DMSO–KOH–O2 via oxidative nucleophilic substitution of hydrogen to give the corresponding 6-hydroxyalkylamino derivatives. The reaction of 1,3,7-triazapyrene with sodium amide in DMSO at room temperature yields 1,3,7-triazapyren-6-amine. N-Alkyl-8-methoxy-1,3,7-triazapyren-6-amines or N,N'-dialkyl- 1,3,7-triazapyrene-6,8-diamines are formed in reactions of 6,8-dimethoxy-1,3,7-triazapyrene with alkylamines or amino alcohols in DMSO, depending on the conditions.