Acyclic analogues of purine and imidazole nucleosides

Abstract

Abstract Hydroxyl‐protected derivatives of 1‐ and 3‐(2‐hydroxyethoxymethyl)imidazoles ( 4,5,7‐10 ) have been prepared from 5‐amino‐4‐carbamoylimidazoles ( 2 ). The protected derivatives were converted to acyclic analogues of imidazole nucleosides ( 6 ) or subjected to various cyclisation reactions leading to 9‐(2‐hydroxy‐ethoxymethyl)‐substituted 2‐methyl‐, 2‐phenyl‐ and 2‐azahypoxanthines ( 18,13 and 20 , respectively) and 1‐methylguanine ( 28 ). For assignment of structures to isomeric imidazole and purine derivatives, 13 C chemical shifts have been used.