The conversion of an aziridine plus a phenyl-substituted amine oxide or aminoether to a benzodiazepine derivative |
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Authors: | Matthew T HancockRobert E Minto Allan R Pinhas |
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Institution: | a Department of Chemistry, University of Cincinnati, PO Box 210172, Cincinnati, OH 45221, USA b Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA |
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Abstract: | 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. |
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