This study describes the synthesis of 2-amino-4-(substituted/hetero)aryl-5-oxo-4,5-dihydropyrano[3,2-c]chromene/quinolone-3-carbonitriles, with improved yields obtained in DMF at 90 °C, using sulfated polyborate as a catalyst. The catalyst provides excellent results and shows good functional group tolerance, with yields ranging from 82 to 93% for various aromatic and heteroaromatic (substituted/hetero)arylidene malononitriles. The key advantages of this method include shorter reaction times and higher product yields. This optimized reaction condition enabled the synthesis of valuable heterocyclic compounds from readily available reactants. In total, 32 substrates were successfully synthesized under optimized reaction conditions. The synthesized compounds were characterized using FTIR, 1H NMR, 13C{1H} NMR, high-resolution mass spectrometry, and elemental analysis.
Graphical abstract
Sulfated Polyborate was used as an acid catalyst in organic transformations. It efficiently catalyzed the 4-hydroxycoumarin, chloro substituted 4-hydroxycoumarin, 4-hydroxy-1-methylquinolin-2(1H)-one, bromo substituted 4-hydroxy-1-methylquinolin-2(1H)-one with (subs./het)arylidene malononitriles in DMF as a solvent producing 2-amino-4-(subs./het)aryl-5-oxo-4,5-dihydropyrano[3,2-c]chromene/ quinolone-3-carbonitriles with excellent yield.
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