Substituted 1,4-Benzoxazepines, 1,5-Benzoxazocines, and N- and S-Variants

Nucleophilic cleavage of enantiomerically pure 1,2-cyclic sulfamidates with phenol, aniline, and thiophenol nucleophiles, followed by a Mitsunobu reaction, including use of a o-quinomethide variant of this process, provides an entry to substituted 1,4-tetrahydrobenzoxazepines, benzothiazepines, and benzodiazepines. Application of this methodology to 1,3-cyclic sulfamidates affords a parallel entry to the analogous substituted 1,5-benzoxazocines and 1,5-benzodiazocines.