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A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet–Spengler reaction of aziridines and epoxides with indoles/aldehydes

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Abstract

A simple and efficient synthetic route to various 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyrano[3,4-b]indoles in high yields and stereoselectivity via LiClO4-catalyzed SN2-type ring opening of aziridines and epoxides with indoles followed by p-toluenesulfonic acid (PTSA) catalyzed Pictet–Spengler reaction is described.

Graphical abstract: A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet–Spengler reaction of aziridines and epoxides with indoles/aldehydes

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Publication details

The article was received on 27 Sep 2019, accepted on 03 Dec 2019 and first published on 04 Dec 2019


Article type: Paper
DOI: 10.1039/C9OB02098E
Org. Biomol. Chem., 2020, Advance Article

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    A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet–Spengler reaction of aziridines and epoxides with indoles/aldehydes

    I. A. Wani, G. Goswami, S. Sk, A. Mal, M. Sayyad and M. K. Ghorai, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02098E

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