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A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles

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Abstract

An efficient metal-free approach has been devised for the synthesis of novel β-carboline C-1 tethered 2,3-dihydropyrroles and pyrroles via one-pot assembly involving 1-formyl β-carbolines, aryl methyl ketones, and isonitriles. The reaction advances through the formation of β-carboline linked enones followed by [3+2] cycloaddition with isonitriles. This methodology features an operationally simple procedure, multicomponent character, high atom economy, a broad substrate scope, short reaction times, and high regioselectivity with excellent yields. The scope of the process was exemplified via the synthesis of a library of 34 novel compounds with significant diversity.

Graphical abstract: A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles

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Article information


Submitted
07 May 2020
Accepted
24 Jun 2020
First published
24 Jun 2020

New J. Chem., 2020, Advance Article
Article type
Paper

A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles

M. Singh, A. K. Paul and V. Singh, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ02315A

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