The conversion of an aziridine plus a phenyl-substituted amine oxide or aminoether to a benzodiazepine derivative

The conversion of an aziridine to a tetrahydrobenzodiazepine derivative using LiI, an iron carbonyl complex, and an amine oxide, or using LiI and a gem-aminoether is studied. The reaction of an aziridine with LiI and a phenyl-substituted iminium salt generates mainly a 1,2-diamine. The addition of t-butoxide to the iminium reaction changes the product ratio leading to a diamine as the minor product and a benzodiazepine as the major product. The structure proof of the tetrahydrobenzodiazepine derivative and the mechanism of these transformations are discussed.