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Synthesis of Pyrano[2,3-f]chromen-2-ones vs. Pyrano[3,2-g]chromen-2-ones through Site Controlled Gold-Catalyzed Annulations

Abstract

The regioselective access to 10-substituted-2H,8H-pyrano[2,3-f]chromen-2-ones through the gold-catalyzed intramolecular hydroarylation of readily available 7-(prop-2-yn-1-yloxy)-2H-chromen-2-one derivatives at their C-8 congested position was investigated by tuning the electronic and steric properties of the ligand on the gold complex. On the other hand the combination of the JohnPhosAu(MeCN)SbF6 catalyzed intramolecular hydroarylation of 8-iodo-7-(prop-2-yn-1-yloxy)-2H-chromen-2-one derivatives followed by the selective palladium/formate C-I reduction allows for the exclusive formation of the 2H,8H-pyrano[3,2-g]chromen-2-one regioisomers. The development of these two protocols provides versatile synthetic tools required for the biological activities exploration of these new pyranocoumarin derivatives.

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Publication details

The article was received on 31 Jul 2019, accepted on 08 Nov 2019 and first published on 09 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB01695C
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Synthesis of Pyrano[2,3-f]chromen-2-ones vs. Pyrano[3,2-g]chromen-2-ones through Site Controlled Gold-Catalyzed Annulations

    A. Iazzetti, A. Arcadi, A. Ciogli, G. Fabrizi, A. Fochetti, R. Franzini, F. Ghirga and A. Goggiamani, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB01695C

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