ELECTROPHILIC AMINATION OF IMIDAZOLE MOIETIES OF 9-ETHYLGUANINE AND 1-METHYLBENZIMIDAZOLE DERIVATIVES AND REACTIVITIES OF N-AMINATED PRODUCTS

Electrophilic amination of four 9-ethylguanine derivatives and seven 1 -methylbenzimidazole derivatives with 2,4-dinitrophenoxyamine was carr ied out. N-amination proceeded at the imidazole moiety of these compou nds with pKa's of more than 3.2. Treatment of these N-aminated derivat ives with 0.1 N NaOH gave different results depending on their structu res. Reactivity of the imidazole moiety to electrophilic amination and the reaction pathways of N-aminated compounds with alkaline treatment are discussed.