The functionalized 3,4-dihydroquinolin-2-one nucleus has been assembled in good to high yields through the sequential reaction of readily available N-Ts-o-aminobenzyl alcohols with 5-substituted Meldrum's acid derivatives under mild basic conditions. Highly diastereoselective synthesis of 3-substituted-4-phenyl-1-tosyl-3,4-dihydroquinolin-2(1H)-ones was accomplished from N-(2-(hydroxy(phenyl)methyl)phenyl)-4-methylbenzenesulfonamide under the same reaction conditions. Regarding the reaction mechanism, we hypothesized that the formation of dihydroquinolones proceeds through the in situ generation of aza-o-QMs followed by conjugate addition of enolate/cyclization/elimination of acetone and CO2

Arcadi, A., Calcaterra, A., Fabrizi, G., Fochetti, A., Goggiamani, A., Iazzetti, A., Marrone, F., Mazzoccanti, G., Serraiocco, A., One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids, <<ORGANIC &amp; BIOMOLECULAR CHEMISTRY>>, 2022; (20): 3160-3173. [doi:10.1039/d2ob00289b] [http://hdl.handle.net/10807/201681]

One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids

Iazzetti, Antonia
;
2022

Abstract

The functionalized 3,4-dihydroquinolin-2-one nucleus has been assembled in good to high yields through the sequential reaction of readily available N-Ts-o-aminobenzyl alcohols with 5-substituted Meldrum's acid derivatives under mild basic conditions. Highly diastereoselective synthesis of 3-substituted-4-phenyl-1-tosyl-3,4-dihydroquinolin-2(1H)-ones was accomplished from N-(2-(hydroxy(phenyl)methyl)phenyl)-4-methylbenzenesulfonamide under the same reaction conditions. Regarding the reaction mechanism, we hypothesized that the formation of dihydroquinolones proceeds through the in situ generation of aza-o-QMs followed by conjugate addition of enolate/cyclization/elimination of acetone and CO2
2022
Inglese
Arcadi, A., Calcaterra, A., Fabrizi, G., Fochetti, A., Goggiamani, A., Iazzetti, A., Marrone, F., Mazzoccanti, G., Serraiocco, A., One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids, <<ORGANIC &amp; BIOMOLECULAR CHEMISTRY>>, 2022; (20): 3160-3173. [doi:10.1039/d2ob00289b] [http://hdl.handle.net/10807/201681]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10807/201681
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