Synthesis of 1,5-Benzodiazepine Nucleosides

Abstract

The phenolic beta -diketones I prepared by modified Baker-Venkataraman rearrangement were converted to benzodiazepine derivatives II by treatment with o-phenylenediamine. Coupling of benzodiazepine derivatives II with acetobromo sugars in presence of mercuric cyanide and nitromethane gave acetylated sugar derivatives of benzodiazepines III. The nucleosides IV were obtained by the deacetylation of compounds III. Structures of all intermediates and final products were confirmed with the help of modern spectroscopic methods.