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. Issue 33 (6th August 2019)

• Record Type: Journal Article
• Authors: Hajra, Saumen; Maity, Subrata; Roy, Sayan; Das, Dhiraj
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 33(2019)
• Page Start: 7747
• Page End: 7759
• Publication Date: 2019-08-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01249d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A strategy for the construction of both C(3)–N(1′) bisindoles and C(3)–N(1′) diindolylmethane has been explored via tuning of the nucleophilicity of indoline/indole to spiro-epoxyoxindole. 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 SN 2 mechanism provides C(3)–N(1′) diindolylmethane.