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.