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Communication | Special issue | Vol 50, No. 1, 1999, pp.43-46
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)20
Synthesis and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones

Yoshinori Tominaga,* Noriko Yoshioka, Seigo Kataoka, Yasuhiro Shigemitsu, Takashi Hirota, and Kenji Sasaki

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Substituted anilines reacted with methyl1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate (1) in refluxing methanol 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-methylpyrrolo[3,4-b]quinoline derivatives (4a-e) by heating in diphenyl ether. Reaction of 4a-e with hydrazine hydrate gave 10-hydroxypyridazino[4,5-b]quinoline-1,4(2H,3H)-diones (5a-e) in good yields. The desired 10-aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones (8a-e) were obtained by the chlorination of 4a-e with phosphorus 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 H2O2 and horseradish peroxidase in a solution of a phosphate buffer pH 8.0.