Formation of furo[3,2-c]quinolone-2-carbonitriles and 4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides from reaction of quinoline-2,4-diones with 2-[bis(methylthio)methylene]malononitrile

Quinoline-2,4-diones reacted with 2-[bis(methylthio)methylene]malononitrile in DMF/Et 3 N to produce 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2- c ]quinolone-2-carbonitriles and 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2- c ]quinolone-2-carboxamides in state of 2-imino-substituted 4-(methylthio)-5,6-dih...

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Bibliographic Details
Published in:Monatshefte für Chemie 2020-02, Vol.151 (2), p.223-229
Main Authors: Aly, Ashraf A., Ishak, Esam A., Shwaky, Ahmed M., Mohamed, Asmaa H.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Malononitrile
Methylene
NMR
Nuclear magnetic resonance
Organic Chemistry
Original Paper
Physical Chemistry
Quinoline
Theoretical and Computational Chemistry
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Summary:Quinoline-2,4-diones reacted with 2-[bis(methylthio)methylene]malononitrile in DMF/Et 3 N to produce 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2- c ]quinolone-2-carbonitriles and 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2- c ]quinolone-2-carboxamides in state of 2-imino-substituted 4-(methylthio)-5,6-dihydro-2 H -pyrano[3,2- c ]quinolone-3-carbonitriles. The structures of all new products were proved using NMR, IR, and mass spectral data. The possible mechanism for the reaction is also discussed. Graphic abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-019-02541-0