Tandem Michael addition–Fries rearrangement of sorbylanilides: a convenient one pot synthesis of novel benzo[b]azocin-6-ones

The Letter pertains to an unprecedented tandem Michael addition–Fries rearrangement of sorbyl anilides resulting in a convenient one pot synthesis of novel benzo[b]azocin-6-ones. The reaction is thought to proceed via a δ-lactam intermediate, earlier considered un-reactive for Fries rearrangement. The proposed mechanism was further supported by examining the reactions of α,β-unsaturated anilides. Their inability to undergo any transformation under similar reaction conditions, especially the Fries–Michael rearrangement, indirectly validated the mechanism.