Reaction of 9-substituted adenines with chloroacetic anhydride. Formation of novel mesoionic imidazopyrines
Abstract
Reaction of the 9-substituted adenines (1) with chloroacetic anhydride in boiling toluene has resulted in the formation of the novel mesoionic imidazopurines (3) in moderate to good yields. The reaction apparently involves an intramolecular alkylation of the initially formed 9-substituted N6-chloroacetyladenines (2) at N-1, which is in contrast with the exclusive N7-alkylation in the reaction of 9-substituted N6-acyladenines with alkyl halides.