TY - JOUR
T1 - Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls
AU - Marsicano, Vincenzo
AU - Arcadi, Antonio
AU - Chiarini, Marco
AU - Fabrizi, Giancarlo
AU - Goggiamani, Antonella
AU - Iazzetti, Antonia
PY - 2021
Y1 - 2021
N2 - 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.
AB - 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.
KW - 4H-pyrano[3,4-c]quinoline core
KW - Sequential reactions
KW - 4H-pyrano[3,4-c]quinoline core
KW - Sequential reactions
UR - http://hdl.handle.net/10807/198667
U2 - 10.1039/d1ob00795e
DO - 10.1039/d1ob00795e
M3 - Article
SN - 1477-0520
VL - 19
SP - 5177
EP - 5190
JO - ORGANIC & BIOMOLECULAR CHEMISTRY
JF - ORGANIC & BIOMOLECULAR CHEMISTRY
ER -