SYNTHESIS AND CHEMILUMINESCENCE OF 10-HYDRODXY-AND 10-AMINOPYRIDAZINO4,5-bQUINOLINE-1,4(2H,3H)-DIONES

摘要

Abstract-Substituted anilines reacted with methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate (1) in refluxing methanlo to give the corresponding methyl 1-methyl-2,5-dioxo-4-phenylamino-3-pyrroline-3-carboxylates (3a-e) which were converted in good yields to 2-methylpyrrolo3,4-bquinoline derivative (4a-e)by heating in diphenyl ether.Reaction of 4a-e with hydrazine hydrate gave 10-hydroxypyridazino4,5-bquinoline-1,4(2H,3H)-diones (5a-e) in good yields.The desired 10-aminopyridazino4,5-bquinoline-1,4(2H,3H)-diones(8a-e)were obtained by the chlorination of 4a-e with phosphours oxychloride followed by ammonolysis with 28 ammonium hydroxide in good yields.Compounds (5) and (8) were found to be efficiently chemiluminescent in a similarly to luminol in the presence of H_2 O_2 and horseradish peroxidase in a solution of a phosphate buffer pH 8.0.