Dual Behavior of Ammonium Acetate for the Synthesis of Diverse Symmetrical/Unsymmetrical Bis[1,3]oxazines Possessing Anticancer Activity

摘要

A simple and efficient approach was developed to synthesize symmetrical/unsymmetrical bis[1,3]oxazines using ammonium acetate with controllable substitution patterns in a one-pot fashion. In a representative crystal structure, the [1,3]oxazine ring is in a distorted semichair conformation with C2-carbon and nitrogen atoms residing above and below the naphthalene plane, leading to strain in the ring that allows ring-opening polymerization to take place. A few of the derivatives were found to possess anticancer activity. This current modest protocol affords numerous advantages such as mild reaction condition, shorter reaction time, operational simplicity, and excellent yield.