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Issue 42, 2018
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An unexpected thermal-ring-rearrangement of benzochromenes to inden-3-yl-naphthols with pTsOH

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Abstract

Described here is the first report of an unexpected thermal-ring rearrangement (TRR) of benzochromenes to indene derivatives promoted by pTsOH. This cascade ring-rearrangement proceeds through the protonation of benzochromenes by an acid catalyst followed by ring-opening and ring-closure by an intramolecular Friedel–Crafts cyclization to provide a new bicyclic framework, inden-3-yl-naphthols bearing a quaternary center, which also exhibited atropisomerism. Regioselectivity, broad substrate scope, high yields, solvent-free conditions and atom economy are the additional high points of this ring-rearrangement.

Graphical abstract: An unexpected thermal-ring-rearrangement of benzochromenes to inden-3-yl-naphthols with pTsOH

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Publication details

The article was received on 13 Sep 2018, accepted on 03 Oct 2018 and first published on 04 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02264J
Citation: Org. Biomol. Chem., 2018,16, 7920-7925
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    An unexpected thermal-ring-rearrangement of benzochromenes to inden-3-yl-naphthols with pTsOH

    S. Yaragorla and T. Khan, Org. Biomol. Chem., 2018, 16, 7920
    DOI: 10.1039/C8OB02264J

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