Synthesis of morphinans with diversely functionalized benzoxazole moieties

摘要

Three independent strategies have been established for the synthesis of morphinans with oxazole moieties derived from the aminophenol function of 2-am-inomorphine. All the procedures possess the ability to furnish diversely substituted 2'-oxazole moieties which are considered significant in view of the presented density functional studies on the spatial and electrostatic properties of the proximal functions of the 3-hydroxyl of the mor-phinan backbone. These data are considered important for neuropharmacological development of potential kappa antagonist morphinans. The second strategy was extended to the direct vinylation of oxazoles to form more complex benzoxazole-type morphinans.