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Issue 27, 2016
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A highly efficient one-pot synthesis of indenopyridine-fused spirocyclic systems

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Abstract

Structurally diverse spirooxindoles incorporating a medicinally privileged indenopyridine moiety have been synthesized regioselectively via multi-component reaction of 1,1-dicyanomethylene-3-indanone, isatins, and malononitrile in the presence of amines in ethanol as an environmentally friendly medium under mild conditions. This domino process includes a [5 + 1] hetrocyclization that occurs under metal-free conditions. The product is a spirooxindole-fused indenopyridine salt that was successfully neutralized by dilute hydrochloric acid. Replacement of isatins with indenoquinoxalines led to the production of dihydrospiro[indeno[1,2-b]quinoxaline-indenopyridine salts in good yields.

Graphical abstract: A highly efficient one-pot synthesis of indenopyridine-fused spirocyclic systems

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Publication details

The article was received on 11 Jan 2016, accepted on 16 Feb 2016 and first published on 16 Feb 2016


Article type: Paper
DOI: 10.1039/C6RA00869K
Citation: RSC Adv., 2016,6, 22306-22311
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    A highly efficient one-pot synthesis of indenopyridine-fused spirocyclic systems

    G. I. Shakibaei and A. Bazgir, RSC Adv., 2016, 6, 22306
    DOI: 10.1039/C6RA00869K

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