A Convenient Method for the Synthesis of 1,5-benzodiazepin-2-one

Abstract

New 3-hydroxy-1,5-benzodiazepin-2-ones were synthesized through condensation between ophenylenediamines with glycidic ester. Alkylation and oxidation of some of the obtained compounds were also explored in different conditions yielding various oxidized and alkylated benzodiazepines. The structural elucidation of the synthesized compounds was achieved by MS, NMR spectroscopy and also through X-ray diffraction analysis. The glycidic ester was thus shown to be an interesting synthon in the synthesis of new 1,5-benzodiazepines used in alkylation and oxidation reactions.

Enantioselective Synthesis of 4-Substituted 4,5-Dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis Base-Catalyzed Hydrosilylation

“…Solid-phase synthetic strategies have been applied to prepare 4,5-dihydro-1 H -[1,5]­benzodiazepin-2-one derivatives. , Xiaoxia Wang and co-workers have demonstrated that o -phenylenediamine reacted with N -cinnamoylbenzotriazoles via 1,4-addition to afford 1,3,4,5-tetrahydro-1,5-benzodiazepin-2-ones . In addition, several other groups also reported their studies on this subject . However, to the best of our knowledge, only one example of enantioselective synthesis of these compounds has been described.…”