6-Azapurines. Part 3. Covalent σ-adducts of the imidazo[4,5-e]-as-triazine ring system
Abstract
7-Methylimidazo[4.5-e]-as-triazin-3(2H)-one, imidazo[4,5-e]-as-triazin-3(2H)-one, and 5-methyl-imidazo[4,5-e]-as-triazin-3(2H)-one have been synthesized from their respective 5,6-diamino-as-triazin-3-ones and selected one-carbon delivering reagents. These 6-azapurines undergo covalent hydration across the azomethine bond located in the imidazole portion of the ring. In water, the σ-adducts ring open to certain as-triazin-3-ones whose structures were identified by NMR (1H and 13C) spectroscopy. These as-triazin-3-ones provided evidence for the described mode of cleavage.