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, Kenji Sasaki

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Substituted anilines reacted with methyl 1-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.

Original languageEnglish
Pages (from-to)43-46
Number of pages4
JournalHeterocycles
Volume50
Issue number1
Publication statusPublished - Jan 1 1999

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Chemiluminescence
Luminescence
hydrazine
Aniline Compounds
Ammonium Hydroxide
Luminol
Chlorination
Halogenation
Horseradish Peroxidase
Heating
Methanol
Buffers
Phosphates
Derivatives
quinoline
pyrroline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Tominaga, Y., Yoshioka, N., Kataoka, S., Shigemitsu, Y., Hirota, T., & Sasaki, K. (1999). Synthesis and chemiluminescence of 10-hydroxy- and 10- aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones. Heterocycles, 50(1), 43-46.

Synthesis and chemiluminescence of 10-hydroxy- and 10- aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones. / Tominaga, Yoshinori; Yoshioka, Noriko; Kataoka, Seigo; Shigemitsu, Yasuhiro; Hirota, Takashi; Sasaki, Kenji.

In: Heterocycles, Vol. 50, No. 1, 01.01.1999, p. 43-46.

Research output: Contribution to journalArticle

Tominaga, Y, Yoshioka, N, Kataoka, S, Shigemitsu, Y, Hirota, T & Sasaki, K 1999, 'Synthesis and chemiluminescence of 10-hydroxy- and 10- aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones', Heterocycles, vol. 50, no. 1, pp. 43-46.
Tominaga Y, Yoshioka N, Kataoka S, Shigemitsu Y, Hirota T, Sasaki K. Synthesis and chemiluminescence of 10-hydroxy- and 10- aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones. Heterocycles. 1999 Jan 1;50(1):43-46.
Tominaga, Yoshinori ; Yoshioka, Noriko ; Kataoka, Seigo ; Shigemitsu, Yasuhiro ; Hirota, Takashi ; Sasaki, Kenji. / Synthesis and chemiluminescence of 10-hydroxy- and 10- aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones. In: Heterocycles. 1999 ; Vol. 50, No. 1. pp. 43-46.
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