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Current Green Chemistry

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ISSN (Online): 2213-347X

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Research Article

Glycogen: A Novel Biopolymer Catalyst for the One-Pot Synthesis of Spirooxindoles, Spiro-Acenaphthylenes, and Spiro-2-Aminopyrans Derivatives under Mild Conditions

Author(s): Nahid Ahmadi*, Malek Taher Maghsoodlou, Mahmoud Nassiri and Forough Jalili Milani*

Volume 11, Issue 4, 2024

Published on: 21 March, 2024

Page: [369 - 378] Pages: 10

DOI: 10.2174/0122133461280455240305061938

Price: $65

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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.

Methods: 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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