Synthesis of sotne new heterocyclic compounds derived frotn 1,5- benzodiazepine derivatives

Abstract

The work presented deals with the synthesis of l-or 3- substituted-, fused and spiro(l ,5)benzodiazepines. Mannich bases 2-4 or sulfides 5 and 6 were obtained from the reaction of 1,3-dihydro-4-phenyl (1,5)benzodiazepin- 2-one 1 with the proper secondary amines or mercaptans. Treatment •of compound 1 with bromine in 1:1 molar ratio gave the corresponding 3-bromo derivative 8, which in turn reacted with different nucleophiles to get the corresponding 3-substituted derivatives 10, 12,14,16, 18, 20, 22, 24, 25, 26, 27 and 28. The cyclized compounds 11,13, 15, 17, 19, 21 and 23 were achieved on refluxing compounds 10, 12,14,16, 18, 20 and 22, respectively in diphenyl ether. Benzoylation of compound 1 with benzoyl chloride afforded the corresponding 1-benzoyl derivative 7, which reacted with bromine in 1:2 molar ratio to yield the corresponding 3,3- dibromo derivative 29. Spiro(1,5)benzodiazepinones 30-38 were obtained by reacting compound 29 with the proper bidentates. The reaction of compound 1 with phosphorus pentasulfide yielded the corresponding 2-thione derivative 9, which reacted with malononitrile to give compound 39. Fused (1,5)benzodiazepines 40-45 were synthesized by reacting compound 39 with formaldehyde and the proper primary amines, chloroacetonitrile or phenacyl bromide. While the spiro benzodiazepines 46-58 were obtained via the reaction of