Synthesis of 2-dialkylamino-6- and -7-hydroxy-5,8-dioxoquinolines

Wayne C. Fleming, George Pettit

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A synthetic route to 2-substituted 6- and -7-hydroxy-5,8-dioxoquinolines has been evaluated. Reaction of 5,7-dinitro-8-hydroxycarbostyril (4) with phosphorus oxychloride followed by reaction with piperidine or morpholine gave the 2-substituted 5,7-dinitro-8-quinolinols 5d and 5e. Catalytic hydrogenation, oxidation, and acid hydrolysis gave the corresponding 7-hydroxy-5,8-dioxoquinolines 9a and 9b. A similar sequence was used to proceed from 5-hydroxy-6,8-dinitrocarbostyril (12) via 2-chloro-6,8-dinitro-5-quinolinol (13a) and 2-piperidino-6,8-dinitro-5-quinolinol (13b) to 2-piperidino-6-hydroxy-5,8-dioxoquinoline (14a).

Original languageEnglish (US)
Pages (from-to)3490-3493
Number of pages4
JournalJournal of Organic Chemistry
Volume36
Issue number23
StatePublished - 1971

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Hydroxyquinolines
Oxyquinoline
Hydrogenation
Hydrolysis
Oxidation
Acids

ASJC Scopus subject areas

  • Organic Chemistry

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Synthesis of 2-dialkylamino-6- and -7-hydroxy-5,8-dioxoquinolines. / Fleming, Wayne C.; Pettit, George.

In: Journal of Organic Chemistry, Vol. 36, No. 23, 1971, p. 3490-3493.

Research output: Contribution to journalArticle

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abstract = "A synthetic route to 2-substituted 6- and -7-hydroxy-5,8-dioxoquinolines has been evaluated. Reaction of 5,7-dinitro-8-hydroxycarbostyril (4) with phosphorus oxychloride followed by reaction with piperidine or morpholine gave the 2-substituted 5,7-dinitro-8-quinolinols 5d and 5e. Catalytic hydrogenation, oxidation, and acid hydrolysis gave the corresponding 7-hydroxy-5,8-dioxoquinolines 9a and 9b. A similar sequence was used to proceed from 5-hydroxy-6,8-dinitrocarbostyril (12) via 2-chloro-6,8-dinitro-5-quinolinol (13a) and 2-piperidino-6,8-dinitro-5-quinolinol (13b) to 2-piperidino-6-hydroxy-5,8-dioxoquinoline (14a).",
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T1 - Synthesis of 2-dialkylamino-6- and -7-hydroxy-5,8-dioxoquinolines

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N2 - A synthetic route to 2-substituted 6- and -7-hydroxy-5,8-dioxoquinolines has been evaluated. Reaction of 5,7-dinitro-8-hydroxycarbostyril (4) with phosphorus oxychloride followed by reaction with piperidine or morpholine gave the 2-substituted 5,7-dinitro-8-quinolinols 5d and 5e. Catalytic hydrogenation, oxidation, and acid hydrolysis gave the corresponding 7-hydroxy-5,8-dioxoquinolines 9a and 9b. A similar sequence was used to proceed from 5-hydroxy-6,8-dinitrocarbostyril (12) via 2-chloro-6,8-dinitro-5-quinolinol (13a) and 2-piperidino-6,8-dinitro-5-quinolinol (13b) to 2-piperidino-6-hydroxy-5,8-dioxoquinoline (14a).

AB - A synthetic route to 2-substituted 6- and -7-hydroxy-5,8-dioxoquinolines has been evaluated. Reaction of 5,7-dinitro-8-hydroxycarbostyril (4) with phosphorus oxychloride followed by reaction with piperidine or morpholine gave the 2-substituted 5,7-dinitro-8-quinolinols 5d and 5e. Catalytic hydrogenation, oxidation, and acid hydrolysis gave the corresponding 7-hydroxy-5,8-dioxoquinolines 9a and 9b. A similar sequence was used to proceed from 5-hydroxy-6,8-dinitrocarbostyril (12) via 2-chloro-6,8-dinitro-5-quinolinol (13a) and 2-piperidino-6,8-dinitro-5-quinolinol (13b) to 2-piperidino-6-hydroxy-5,8-dioxoquinoline (14a).

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