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Gold-catalyzed cascade reactions of 4H-furo[3,2-b]indoles with propargyl esters: synthesis of 2-alkenylidene-3-oxoindolines

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Abstract

2-Alkenyliden-indolin-3-ones were synthesised in high yields via a cascade reaction between 4H-furo[3,2-b]indoles and propargyl esters. The cascade sequence involves the initial formation of a gold-carbene species via cationic gold(I) catalysed 1,2-acyloxy migration of properly substituted propargyl esters followed by the addition of gold-carbene to furoindole and successive furan ring-opening affording the final products. The obtained compounds contain an extended π-system linked at the C2 of the indolin-3-ones; they show intense colouration (from yellow to purple) and are characterised by UV measurements.

Graphical abstract: Gold-catalyzed cascade reactions of 4H-furo[3,2-b]indoles with propargyl esters: synthesis of 2-alkenylidene-3-oxoindolines

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Publication details

The article was received on 15 May 2019, accepted on 09 Jul 2019 and first published on 10 Jul 2019


Article type: Research Article
DOI: 10.1039/C9QO00647H
Org. Chem. Front., 2019, Advance Article

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    Gold-catalyzed cascade reactions of 4H-furo[3,2-b]indoles with propargyl esters: synthesis of 2-alkenylidene-3-oxoindolines

    E. Brambilla, V. Pirovano, M. Giannangeli, G. Abbiati, A. Caselli and E. Rossi, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00647H

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