One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels-Alder Cycloaddition.

A rapid and efficient one-pot synthesis of a series of four novel nuevamine aza-analogues is described based on the oxidative Ugi-type reaction and aza-Diels-Alder reaction as post-functionalization. A simple IBX-mediated oxidation of a secondary amine followed by isonitrile α-addition and finally an aza-Diels-Alder cycloaddition provides the desired compounds in excellent overall yields considering the short reaction time, atom economy, and the molecular complexity of the final products. This protocol presents a highly attractive procedure for the rapid generation of fused polyheterocycles. [ABSTRACT FROM AUTHOR]