Synthesis of 5, 6-, 5, 8- and 7, 8-Isoquinolinediones from the Corresponding Isoquinolinols and Dimethoxyisoquinolines

Yoshiyasu KITAHARA; Tatsuya NAKAI; Shinsuke NAKAHARA; Manabu AKAZAWA; Masaro SHIMIZU; Akinori KUBO

doi:10.1248/cpb.39.2256

Yoshiyasu KITAHARA, Tatsuya NAKAI, Shinsuke NAKAHARA, Manabu AKAZAWA, Masaro SHIMIZU, Akinori KUBO

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Keywords: synthesis, 5, 8-isoquinolinedione, 5, 6-isoquinolinedione, 7, 8-isoquinolinedione, oxidation, oxidative demethylation, cerium(IV) ammonium nitrate, silver(II) oxide, potassium nitrosodisulfonate

JOURNAL FREE ACCESS

1991 Volume 39 Issue 9 Pages 2256-2263

DOI https://doi.org/10.1248/cpb.39.2256

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Abstract

5, 8-Isopuinolinediones (12, 18, 25), 7, 8-isoquinolinediones (14, 19) and 5, 6-isoquinolinediones (26) were synthesized by oxidative demethylation of the corresponding dimethoxyisoquinolines with cerium(IV) ammonium nitrate or silver(II) oxide. 8-Dialkylamino-5, 6-isoquinolinediones (31) and 3, 5-bis(dialkylamino)-7, 8-isoquinolinediones (33) were prepared by copper(II)-catalyzed oxidation of the corresponding isoquinolinols with secondary amines. 5, 8-Isoquinolinediones (29, 34, 40) were also prepared.

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