Synthesis of 3-Aryl-3-benzazepines via Aryne [1,2] Stevens Rearrangement of 1,2,3,4-Tetrahydroisoquinolines
Abstract
An efficient method for the synthesis of 3-aryl-3-benzazepines via aryne induced [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines is described. This approach provided a straightforward access to 3-aryl-3-benzazepines in moderate to good yields under transition-metal-free and strong-base-free conditions. Temperature-dependent α-arylated products of the carbonyl group were also obtained. Preliminary mechanistic studies suggest both 3-aryl-3-benzazpeines and α-arylated products of the carbonyl group were generated via the rearrangement of nitrogen ylide intermediates.