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 selective palladium/formate C-I reduction allows for the exclusive formation of 2H,8H-pyrano[3,2-g]chromen-2-one regioisomers. The development of these two protocols provides versatile synthetic tools required for exploring the biological activities of these new pyranocoumarin derivatives.

Arcadi, A., Ciogli, A., Fabrizi, G., Fochetti, A., Franzini, R., Ghirga, F., Goggiamani, A., Iazzetti, A., Synthesis of pyrano[2,3-: f] chromen-2-ones vs. pyrano[3,2-g] chromen-2-ones through site controlled gold-catalyzed annulations, <<ORGANIC & BIOMOLECULAR CHEMISTRY>>, 2019; 17 (47): 10065-10072. [doi:10.1039/c9ob01695c] [http://hdl.handle.net/10807/198666]

Synthesis of pyrano[2,3-: f] chromen-2-ones vs. pyrano[3,2-g] chromen-2-ones through site controlled gold-catalyzed annulations

Iazzetti, Antonia
2019

Abstract

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 selective palladium/formate C-I reduction allows for the exclusive formation of 2H,8H-pyrano[3,2-g]chromen-2-one regioisomers. The development of these two protocols provides versatile synthetic tools required for exploring the biological activities of these new pyranocoumarin derivatives.
2019
Inglese
Arcadi, A., Ciogli, A., Fabrizi, G., Fochetti, A., Franzini, R., Ghirga, F., Goggiamani, A., Iazzetti, A., Synthesis of pyrano[2,3-: f] chromen-2-ones vs. pyrano[3,2-g] chromen-2-ones through site controlled gold-catalyzed annulations, <<ORGANIC & BIOMOLECULAR CHEMISTRY>>, 2019; 17 (47): 10065-10072. [doi:10.1039/c9ob01695c] [http://hdl.handle.net/10807/198666]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10807/198666
Citazioni
  • ???jsp.display-item.citation.pmc??? 2
  • Scopus 10
  • ???jsp.display-item.citation.isi??? 8
social impact