Three-Component Mannich Couplings En Route to Substituted Aminophenol and Benzoxazine Derivatives
19 August 2010 (eFirst)
The three-component Mannich coupling of phenols, primary amines, and aldehydes was investigated. Unexpectedly, benzoxazine products were obtained in most cases, even in instances where steric hindrance would seem to militate against benzoxazine formation. The stereoselective synthesis of such benzoxazines, their hydrolysis to aminophenol derivatives, and the mechanisms involved are presented and discussed.
benzoxazines - phenols - aldehydes - multicomponent reaction - Mannich bases