Characteristics of the oxidative hydroxylation reaction of 7-alkyl-1,3,7-triazapyrenium salts

Abstract

The oxidative hydroxylation of 7-alkyl-1,3,7-triazapyrenium salts depends on the pH of the medium and the oxidant used. The products of monohydroxylation and dihydroxylation have been synthesized.

Oxidative amination and hydroxylation of 1,3,7-triazapyrenes in aqueous medium

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We have already reported the unusual capacity of 1,3,7-triazapyrenes 1a and 1b [1] and 7-alkyl-1,3,7-triazapyrenium salts [2][3][4][5] to react readily in aqueous solution with O-nucleophilic reagents to give mono-and disubstitution products. This is the result clearly not only of the -electron deficiency of these compounds but also the specific peri-fusion structure of this heterocyclic system.

The oxidative amination of the most electrophilic heterocycles such as naphthyridines [6] or 1,2,4-triazine [7] is carried out by action of a solution of KMnO 4 in liquid ammonia.

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