Reaction of 2-(2-amino-4-nitroanilino)ethanol with 3- dimethylaminopropiophenones

Abstract

The reaction of 2-(2-amino-4-nitroanilino)ethanol 5 with 3-dimethylaminopropiophenones 6 is being investigated, aimed to obtain new 1,5-benzodiazepine derivatives. However, mixtures of unpredictable products are being obtained: 1-aryl-3-({2-[2-hydroxyethyl)amino]-5-nitrophenyl}amino)propan- 1-ones 7, hexahydroazeto[1,2-a][1,5]benzo-diazepines 8, dihidrobenzimidazoles 9, acetylated products 10 and tetrahydrobenzodiazepines 11. All structures of the new compounds were determined on the basis of nmr measurements, especially by 1H,1H-and 1H, 13C COSY, DEPT, HSQC, HMBC and NOESY.