Abstract
Background: Glycogen, a naturally occurring macromolecule, in its granular form and without any post-modification was found to be an efficient and eco-friendly bifunctional heterogeneous organocatalyst.
Objective: This catalyst can be useful for the domino synthesis of various spiropyren annulated derivatives through three-component condensation of isathin, malononitrile, and diverse 1,3-dicarbonyl compounds, activated CH-acids, through Knoevenagel-Michael-annulation sequence under mild conditions.
Method: Corresponding spiro derivatives were obtained in high to excellent yields after 5-15 min stirring in 2 mL EtOH and 60°C in the presence of 0.01 g of glycogen, equimolar amounts of isatin/ acenaphthoquinone/ninhydrin, malononitrile, and 1,3-dicarbonyl compounds.
Results: FTIR and 1H NMR spectroscopic showed there isn't any catalyst in the media and desired products were obtained in excellent purity.
Conclusion: Avoiding any transition metal, one-pot, and multicomponent procedure catalyzed by a biopolymer, broad substrate scope, and operational simplicity are essential features of this methodology for the preparation of medicinally important compounds.
Keywords: Spiro heterocyclic compounds, spiroacenaphthylene, spirooxindole, spiro-2-aminopyran, biopolymer, glycogen, malononitrile, 1, 3-dicarbonyl compounds, three-component reaction.
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