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Issue 7, 2016
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Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles

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Abstract

A novel and metal-free I2-mediated intramolecular C2 amidation of indoles under mild reaction conditions is developed. This methodology affords various indole fused tetracyclic compounds, such as benzo[4,5]imidazo[1,2-a]indoles by intramolecular C2 amidation of N-aryl substituted indoles. This C2 sulfonamidative cyclization also offers convenient access to indolo[2,3-b]indoles and dihydroindolo[2,3-b]quinoline from C3 aryl substituted indoles in good to excellent yields. Indolo[2,3-b]quinolines are also synthesized by the domino cyclization–detosylation–aromatization reaction sequence.

Graphical abstract: Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles

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Article information


Submitted
30 Nov 2015
Accepted
08 Jan 2016
First published
08 Jan 2016

Org. Biomol. Chem., 2016,14, 2297-2305
Article type
Paper
Author version available

Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles

S. Badigenchala, V. Rajeshkumar and G. Sekar, Org. Biomol. Chem., 2016, 14, 2297
DOI: 10.1039/C5OB02449H

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