Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines

Abstract

A Chan–Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reaction pathway involving oxygen transfer followed by cyclization.

Keywords

• Chan–Lam
• copper
• nitrone
• oxygen transfer
• pyridine