Synthesis of bridged benzodiazepines by reaction of amines and hydrazine derivatives with 4,6-dibromormethyl-5,2,8-ethanylylidene-5H-1,9-benzodiazacycloundecine

Abstract

Bromination of 4,6-dimethyl-5,2,8-ethanylylidene-5H-1,9-benzodiazacycloundecine with N-bromo-succinimide gives a number of brominated products. Reaction of the dibromo and tribromo derivatives with amines and hydrazine derivatives are described. Amines give dihydro derivatives of bridged 14π annulenes, while the hydrazine derivatives give tetrahydro analogues of bridged 14π annulenes. Oxidation studies with the dihydro- and tetrahydro-annulenes are reported.