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A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles

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Abstract

An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.

Graphical abstract: A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles

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Article information


Submitted
25 Oct 2019
Accepted
16 Dec 2019
First published
17 Dec 2019

Chem. Commun., 2020, Advance Article
Article type
Communication

A rhodium(II) catalysed domino synthesis of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles

N. Kahar, P. Jadhav, R. V. R. Reddy and S. Dawande, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08377D

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