Hetaryl-1,5 benzodiazepines Part I: Synthesis of 3-pyrimidyl- and imidazolyl-1,5-benzodiazepines
Nucleophilic substitution of 3-bromo-4-phenyl-1H-[1,5]benzodiazepin-2-one (1) with thiourea or guanidine in presence of potassium carbonate afforded 1,5-benzodiazepin-3-ylimidothiocarbamate 2 or 1,5- benzodiazepin-3-ylguanidine 3, respectively. Pyrimidylthiobenzodiazepines 5–13 were obtained via the reaction of compound 2 with malononitrile dimer, diethyl malonate, methylenemalononitriles, or a mixture of an aldehyde and β-keto esters or acetylacetone, catalyzed using ceric ammonium nitrate. Reaction of compound 2 or 3 ... Read more