Abstract

A unique and efficient method has been developed for the one-pot synthesis of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines (4aa–4fa) in good yields using o-phenylenediamine, aromatic aldehyde and 3-butyn-2-one in the presence of a catalytic amount of CeCl3·7H2O in ethanol at ambient temperature. An exclusive chemo-/regio-selective formation of substituted isomers of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines was achieved from the different reaction process, by exploiting the strategy based on the variation of electrophilicity of the two electrophilic centers of aromatic aldehyde, 3-butyn-2-one and nucleophilic profiles of substituted o-phenylenediamines. This process offers an easy and efficient synthesis of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines in high yields.

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