Interaction of 2,3-dihydro-1H-benzodiazepinone-2 with epichlorhydrine

Abstract

Derivatives of 1,5-benzodiazepines show various pharmacological activity. The presence of several reactive centers predetermines the possibility of reactions of 1,5-benzodiazepines both with electrophilic and nucleophilic reagents of various types. In addition, these compounds are suitable objects for the synthesis of new tricyclic systems containing a diazepinic cycle. In the article, the interaction of 4-phenyl- and 4-methyl-2,3-dihydro-1Н-1,5-benzodiazepine-2-ones with epichlorhydrin under various conditions is reported. It has been shown that under strongly basic conditions the reactions proceed at the nitrogen atom N 1 and N 1 -glycidyl-1,5- benzodiazepine-2-ones are obtained. The yields of products were 71-79%. Under soft basic conditions the reactions either did not proceed at all or were accompanied by the formation of side-products.