Synthesis and cyclization reactions of 2-(6-methylquinolin-4-yl)malononitriles and ethyl 2-cyano-2-(6-methylquinolin-4-yl)acetates

The nucleophilic substitution reactions of 2,4-dichloro-6-methylquinoline (1) and 4-chloro-6-methylquinolin-2(1H)-one (7) with malononitrile and ethyl cyanoacetate are described. The quinolinylmalononitrile 8a and cyanoacetate 8b were utilized to prepare the novel polyfunctionalized benzoquinolinone...

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Bibliographic Details
Published in:Journal of the Serbian Chemical Society 2006-01, Vol.71 (7), p.721-732
Main Author: Ismail, Mostafa
Format: Article
Language:English
Subjects:
azinylquinolinone
azolylquinolinone
benzoquinolinone
quinolinone
thienoquinolinone
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Summary:The nucleophilic substitution reactions of 2,4-dichloro-6-methylquinoline (1) and 4-chloro-6-methylquinolin-2(1H)-one (7) with malononitrile and ethyl cyanoacetate are described. The quinolinylmalononitrile 8a and cyanoacetate 8b were utilized to prepare the novel polyfunctionalized benzoquinolinones 10a,b, pyridylquinolinones 11a,b, pyrazolylquinolinones 12a-e isoxazolylquinolinone 13, pyrimidylquinolinones 14a-c, thienoquinolinones 15, 16a,b, and pyridothienoquinolinones 17a,b. The structures of the new compounds were based on analytical and spectral results. Opisana je reakcija nukleofilne supstitucije 2,4-dihlor-6-metilhinolina (1) i 4-hlor-6-metilhinolin-2(1H)-ona (7) sa malononitrilom i etil-cijanoacetatom. Hinolinilmalononitril 8a i cijanoacetat 8b, upotrebljeni su za dobivanje novih polifunkcionalizovanih benzohinolinona 10a,b, piridilhinolinona 11a,b pirazolilhinolinona 12a-e, izoksazolilhinolinona 13, pirimidinilhinolinona 14a-c, tijenohinolinona 15, 16a,b i piridotijenohinolinona 17a,b. Strukture novih jedinjenja odredjene su na osnovu analitickih i spektralnih rezultata.
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC0607721I