The consecutive [2+2] cycloaddition-ring expansion route to diastereomeric 1,4-diazepin-5-ones from imino-ketenimines. Alternative intramolecular transamidation of β-lactams |
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Authors: | Mateo Alajarín Angel Vidal Fulgencio Tovar |
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Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30100 Murcia, Spain |
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Abstract: | Azeto1,2-a]imidazoles are prepared by a formal intramolecular 2+2] cycloaddition of imino-ketenimines in which an ethylene chain is linking the nitrogen atoms of both functionalities, bearing a methyl and a phenyl group on the terminal carbon atom of the heterocumulene. By acid-catalyzed hydrolysis these azeto1,2-a]imidazoles are converted into 6,6,7-trisubstituted hexahydro-1,4-diazepin-5-ones, which have been alternatively prepared via intramolecular transamidation of N-(2-aminoethyl)-β-lactams. |
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Keywords: | Ketenimines Cycloadditions Diazepinones Azetidinones Transamidation |
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