Use of the thiomethyl group for activation in the synthesis of 8-hydroxy-1-(spiro-1'-indan)benzazepines

Article abstract of DOI:10.1016/0040-4039(96)01642-5

The utilization of the thiomethyl group to activate an aromatic ring system for closure to form the corresponding conformationally restrained 8-methoxy-7-(methylthio)-3-methyl-1-(spiro-1'-indan)2,3,4,5-tetrahydro -1H-3-benzazepine is described. Subsequent removal of the thiomethyl group with Raney nickel followed by electrophilic substitution allows for the synthesis of other benzazepines that have electron withdrawing groups that normally would be inaccessible.