Cycloaddition of benzoheteroazepine II Reactions and conformations of cycloadducts on 1, 5‐benzothiazepines and 1,5‐benzodiazepines with nitrile imine and nitrile oxides

Abstract

Abstract Benzodiazepine and benzothiazepine derivatives have been well known as therapeutically important compounds. Four new tricyclic heterocyclic compounds, 3a, 4, 5, 11‐tetrahydro‐3 H ‐l,2, 4‐triazalo [4, 3‐ d ] [1, 5] benzothiazepines (3), 3a, 4, 5, 11‐tetrahydro‐3 H ,6 H ‐1, 2, 4‐triazolo[4, 3‐ d ] [1, 5]benzodiazepine (4), 3a, 4, 5, 11‐tetrahydro‐1, 2, 4‐oxadiazolo [4, 5‐ d ] [1, 5]benzothiazepines (5, 6) and 3a,4, 5, 11‐tetrahydro‐6 H ‐1, 2, 4‐oxadiazolo[4, 5 ‐d ] [1, 5] benzodiazepines (7, 8), have been synthesized by 1, 3‐dipolar cycloaddition reactions of 2, 3‐dihydro‐1, 5‐benzothiazepines and 2, 3‐dihydro‐1 H ‐1, 5‐benzodiazepine with benzonitrile N‐ phenylimine and benzonitrile oxides, receptively. The conformations of some cycloadducts and cycloaddition mechanism are described.