REARRANGEMENT OF 4Z-(2-OXO-PROPYLIDENE)-1,5-BENZODIAZEPIN-2- ONES TO 2-ISOXAZOLYLMETHYL-BENZIMIDAZOLE DERIVATIVES

The reaction of hydroxylamine hydrochloride with 4Z-(2-oxo-propylidene)-1,5- benzodiazepin-2-ones 1-12 leads to 2-[(5-methyl-3-isoxazolyl)methyl]benzimidazoles 13- 24. The structures of these biheterocyclic compounds have been unambiguously established by spectral data (NMR, mass spectrometry and single crystal X-Ray diffraction study). Plausible mechanism has been proposed explaining the original rearrangement of the seven membered ring of the 1,5-benzodiazepinones.The compounds obtained have been alkylated by several alkylating reagents in phase transfer catalysis conditions. During the alkylation reactions using ethyl bromide or allyl bromide an interesting oxydation reaction has been highlighted involving the methylene group of the biheterocyclic system. A mechanism of the oxydation reaction has been described.