A divergent domino condensation/biannulation reaction of β-(2-aminophenyl) α,β-ynones with 1,3-dicarbonyls to construct a polycyclic 4H-pyrano[3,4-c]quinoline core has been developed. Thep-TsOH·H2O catalyzed reaction of β-(2-aminophenyl) α,β-ynones with β-ketoesters in ethanol proceeds with good to excellent yields to provide a simple and effective method for the synthesis of functionalized 4H-pyrano[3,4-c]quinolinones. Further elaboration of these latter derivatives with an excess of 20% NH4OH in EtOH at 50 °C helps achieve the synthesis of the perlodinine analogues benzo[c][2,7]naphthyridin-4(3H)-one derivatives in high yields. Moreover, thep-TsOH·H2O mediated reaction of β-(2-aminophenyl) α,β-ynones with β-di-ketones leads to the formation of a variety of structurally diverse 4H-pyrano[3,4-c]quinoline polycyclic ketals by the incorporation of an alcohol solvent molecule in a cascade fashion.
Marsicano, V., Arcadi, A., Chiarini, M., Fabrizi, G., Goggiamani, A., Iazzetti, A., Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls, <<ORGANIC & BIOMOLECULAR CHEMISTRY>>, 2021; 19 (23): 5177-5190. [doi:10.1039/d1ob00795e] [http://hdl.handle.net/10807/198667]
Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls
Iazzetti, Antonia
2021
Abstract
A divergent domino condensation/biannulation reaction of β-(2-aminophenyl) α,β-ynones with 1,3-dicarbonyls to construct a polycyclic 4H-pyrano[3,4-c]quinoline core has been developed. Thep-TsOH·H2O catalyzed reaction of β-(2-aminophenyl) α,β-ynones with β-ketoesters in ethanol proceeds with good to excellent yields to provide a simple and effective method for the synthesis of functionalized 4H-pyrano[3,4-c]quinolinones. Further elaboration of these latter derivatives with an excess of 20% NH4OH in EtOH at 50 °C helps achieve the synthesis of the perlodinine analogues benzo[c][2,7]naphthyridin-4(3H)-one derivatives in high yields. Moreover, thep-TsOH·H2O mediated reaction of β-(2-aminophenyl) α,β-ynones with β-di-ketones leads to the formation of a variety of structurally diverse 4H-pyrano[3,4-c]quinoline polycyclic ketals by the incorporation of an alcohol solvent molecule in a cascade fashion.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.