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Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif

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Abstract

We developed a facile synthetic method to access cyclopenta[b]naphthalene derivatives via the Lewis or Brønsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.

Graphical abstract: Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif

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Publication details

The article was received on 12 Oct 2019, accepted on 21 Nov 2019 and first published on 22 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02211B
Org. Biomol. Chem., 2020, Advance Article

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    Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif

    H. Wei, L. Yu and M. Shi, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02211B

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