Oxidative Dearomatization as a Strategy for a Facile, Metal-Free Synthesis of Vanillyl Benzodiazepines

摘要

isovanillin was conveniently dearomatized into synthetically usefulo-quinol acetate by treatment with phenyliodine(III) diacetate (PIDA) in methylene chloride at low temperature. Subsequent treatment witho-aryl diamines directly furnished vanillyl benzodiazepines in good yields. Vanillyl benzodiazepines, could be the prospective objects of investigation in medicinal chemistry considering the central nervous system depressant activity of benzodiazepines and potent antioxidant and anti-inflammatory activities of vanillyl moiety by being present in a single framework. Herein we propose a simple, metal-free, and efficient approach for the synthesis of vanillyl benzodiazepines via oxidative dearomatization. The regio-chemistry of product isomers were established by NOE studies.