Fused quinoline heterocycles VIII. Synthesis of polyfunctionally substituted pyrazolo[4,3-c]quinol in-4(5H)-ones

Reaction of 2,4-dichloroquinoline-3-carbonitrile (1) with 4-methylpiperidine gave 2-chloro-4-(4-methylpiperidin-1-yl)quinoline-3-carbonitrile (2). Acid hydrolysis of 2 afforded the corresponding 2-quinolinones 3, which were N-alkylated in DMF to form the 1-methyl, -ethyl and -phenacyl quinolinones 6...

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Bibliographic Details
Published in:Journal of chemical research 2008-12, Vol.2008 (12), p.735-737
Main Authors: Mekheimer, Ramadan Ahmed, Refaey, Saeed M, Sadek, Kamal Usef, Hameed, Afaf Mohamed Abdel, Ibrahim, Mohamed Ashry, Shah, Anamik
Format: Article
Language:English
Subjects:
Hydrates
Hydrazines
Hydrolysis
Quinoline
Sodium azides
Synthesis
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Summary:Reaction of 2,4-dichloroquinoline-3-carbonitrile (1) with 4-methylpiperidine gave 2-chloro-4-(4-methylpiperidin-1-yl)quinoline-3-carbonitrile (2). Acid hydrolysis of 2 afforded the corresponding 2-quinolinones 3, which were N-alkylated in DMF to form the 1-methyl, -ethyl and -phenacyl quinolinones 6a-c. Fusion of 6a-c with hydrazine hydrate gave the 3-aminopyrazolo[4,3-c]quinolin-4-ones 8a-c. Diazotisation of 8a,b followed by reaction with sodium azide afforded the novel 3-azidopyrazolo[4,3-c]quinolin-4-ones 9a,b.
ISSN:1747-5198
2047-6507
DOI:10.3184/030823408X392198