S. Fukamachi, Akihiro Kobayashi, H. Konishi
2010
Citations
0
Influential Citations
4
Citations
Journal
Synthesis
Abstract
An efficient method for preparing 2-alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepin-4-ones and 2-alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepine-4-thiones under mild conditions has been developed. Thus, 2-(2-isocyanophenyl)acetamides and 2-(2-isocyanophenyl)thioacetamides, easily available from respective 1-isocyano-2-methylbenzenes, were converted into the corresponding isothiocyanates on treatment with sulfur in the presence of a catalytic amount of selenium, which were then reacted with an equimolar amount to sodium hydride to give 2-(sodiosulfanyl)-3H-4,5-dihydro-1,3-benzodiazepin-4-one and 2-(sodiosulfanyl)-3H-4,5-dihydro-1,3-benzodiazepine-4-thione intermediates, respectively. These intermediates were allowed to react with various alkyl halides to afford the desired benzodiazepinone or benzodiazepinethione derivatives in a one-pot reaction.