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Controlling the regioselectivity of the ring opening of spiro-epoxyoxindoles for efficient synthesis of C(3)–N(1′)-bisindoles and C(3)–N(1′)-diindolylmethane

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Abstract

An efficient strategy for the construction of both C(3)–N(1′) bisindoles and C(3)–N(1′) diindolylmethane has been explored via proper tuning of the nucleophilicity of indoline/indole to spiro-epoxyoxindole. Lewis acid-catalyzed highly regio- as well as chemoselective coupling at the C-3 centre of spiro-epoxyoxindoles with indolines furnishes C(3)–N(1′) bisindoles whereas base mediated and Lewis acid-catalyzed regioselective coupling at the less hindered site of spiro-epoyoxindoles with indoles via the SN2 mechanism provides C(3)–N(1′) diindolylmethane.

Graphical abstract: Controlling the regioselectivity of the ring opening of spiro-epoxyoxindoles for efficient synthesis of C(3)–N(1′)-bisindoles and C(3)–N(1′)-diindolylmethane

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Publication details

The article was received on 30 May 2019, accepted on 23 Jul 2019 and first published on 24 Jul 2019


Article type: Paper
DOI: 10.1039/C9OB01249D
Org. Biomol. Chem., 2019, Advance Article

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    Controlling the regioselectivity of the ring opening of spiro-epoxyoxindoles for efficient synthesis of C(3)–N(1′)-bisindoles and C(3)–N(1′)-diindolylmethane

    S. Hajra, S. Maity, S. Roy and D. Das, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01249D

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