Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Preparation of 4-chloro-3H-benzo[b][1,4]diazepine-2-carbaldehyde , which is used as a key intermediate in the synthesis of chalcones derivatives, via its condensation with some aromatic acetophenone derivatives under ethanol piperidine condition was described. Also illustrated was the reaction of such chalcones with available nucleophilics and reagents of active methylene group to afford new series of fused and isolated pyrazoles, isoxazolines pyrimidines, pyridines, triazolo[1,5-a]pyrimidines, benzo[1,4]oxa(thia)zepines, and pyrido[1,2-a]benzimidazoles incorporating 4-chloro-3H-benzo[b][1,4]diazepine moiety, which have a potential pharmaceutical interest. Furthermore, condensation reaction of 4-chloro-3H-benzo[b][1,4]diazepine-2-carbaldehyde with aromatic amine derivatives to afford the Schiff's bases was described. The CN double bond of the latter compounds has been reacted with chloroketene to give -lactams and with sulfanylacetic acid to give the 2-(4-oxo-1,3-thiazolidinyl)-substituted derivative. The structures of the newly prepared compounds were established by elemental analysis, IR, MS, and 1H NMR spectral analysis.