Synthesis of N-7-Substituted Purines from Imidazole Precursors

Abstract

Synthesis of purines and purine mono-1-oxides from the respective 5-substituted 4-nitroimidazole derivatives is described. The commercially available 4-nitroimidazole, in a few simple steps (including Vicarious Nucleophilic Substitution of Hydrogen), was transformed into: 4-aminoimidazoyl-5-carboximes, N-[1-(4-amino-1H-imidazol-5-yl)methylidene]-N-(aryl)amine derivatives or into 4-amino-5-aminomethyl-imidazole. These intermediates were cyclized to the final products.

Keywords

• purines
• purine N-oxides
• nitroimidazoles
• oximes
• Schiff bases
• isocyanides
• Vicarious Nucleophilic Substitution