Benzotriazole-Assisted Preparations of 2-(Substituted amino)pyridines and Pyrid-2-ones

Base-promoted reactions of benzotriazolyl-containing acetic acid derivatives, 2-(benzotriazol-1-yl)acetonitrile ( 7a ), 2-(benzotriazol-1-yl)acetamide ( 7b ), and (±)-2-(benzotriazol-1-yl)propionamide ( 7c ), with α,β-unsaturated ketones 8 give efficient and regioselective access to previously difficult to attain 3-unsubstituted pyridine derivatives: the 2-(substituted amino)pyridines 14a−k and the 4,6-substituted pyrid-2-ones 15a−h . The pyridine rings result from tandem [3 + 3] annulations involving a Michael addition followed by cyclization.