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Synthesis of spirooxindoles fused with pyrazolo-tetrahydropyridinone and coumarin-dihydropyridine-pyrazole tetracycles by reaction medium dependent isatin-based multicomponent reactions

Abstract

A reaction medium dependent three-component reaction of isatin, 4-hydroxycoumarin and aminopyrazole/aminoisoxazole has been reported under microwave heating conditions for the synthesis of two different types of fused spirooxindoles. The reactions of isatin, aminopyrazole and 4-hydroxycoumarins under microwave irradiations in acetonitrile medium provided spirooxindoles fused with pyrazolo-tetrahydropyridinones by ring opening of the hydroxycoumarin moiety. Similarly, when the same combination was treated in acetic acid as reaction medium, corresponding fused spirooxindoles having a tetracyclic coumarin-dihydropyridine-pyrazole /isoxazole moiety spiro fused with oxindoles were observed. Using this switchable multicomponent reaction, series of medicinally important spiroxindole fused pyrazolo-tetrahydropyridinones and spirooxindole fused coumarin-dihydropyridine-pyrazole/isooxazole tetracycles have been synthesized under metal-free conditions. The salient feature of this methodology are: medium dependent reaction path switching properties, possible to generate two types of products from the same starting materials, metal-free reaction conditions, wide substrate scope, good yields and all the molecules have more than one bioactive moieties.

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Publication details

The article was received on 27 Oct 2018, accepted on 27 Dec 2018 and first published on 28 Dec 2018


Article type: Paper
DOI: 10.1039/C8NJ05465G
Citation: New J. Chem., 2018, Accepted Manuscript
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    Synthesis of spirooxindoles fused with pyrazolo-tetrahydropyridinone and coumarin-dihydropyridine-pyrazole tetracycles by reaction medium dependent isatin-based multicomponent reactions

    R. Mishra, A. Jana, A. Panday and M. L. H. Choudhury, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ05465G

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