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Issue 40, 2019
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Construction of indeno[1,2-a]fluorene via domino reaction of 1,3-indanedione and 3-arylideneindolin-2-ones or chalcones

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Abstract

An efficient synthetic protocol for novel indeno[1,2-a]fluorene derivatives was successfully developed by the base promoted domino reaction of 1,3-indanedione with 3-arylideneindolin-2-ones. The domino reaction in different solvents selectively gave carbamato- or amino-substituted indeno[1,2-a]fluorene in satisfactory yields. Additionally, a similar domino reaction of 1,3-indanediones with chalcones also gave polysubstituted indeno[1,2-a]fluorenes in high yields. The reaction mechanism is believed to proceed with base-promoted dimerization of 1,3-indanedione, Michael condensation, annulation, ring-opening of indolin-2-one and aromatization process.

Graphical abstract: Construction of indeno[1,2-a]fluorene via domino reaction of 1,3-indanedione and 3-arylideneindolin-2-ones or chalcones

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Publication details

The article was received on 13 Aug 2019, accepted on 20 Sep 2019 and first published on 21 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01779H
Org. Biomol. Chem., 2019,17, 9008-9013

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    Construction of indeno[1,2-a]fluorene via domino reaction of 1,3-indanedione and 3-arylideneindolin-2-ones or chalcones

    J. Cao, J. Sun and C. Yan, Org. Biomol. Chem., 2019, 17, 9008
    DOI: 10.1039/C9OB01779H

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