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.

One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids / Arcadi, Antonio; Calcaterra, Andrea; Fabrizi, Giancarlo; Fochetti, Andrea; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 20:15(2022), pp. 3160-3173. [10.1039/D2OB00289B]

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

Arcadi, Antonio;Calcaterra, Andrea;Fabrizi, Giancarlo;Fochetti, Andrea;Goggiamani, Antonella;Iazzetti, Antonia
;
Marrone, Federico;Mazzoccanti, Giulia;Serraiocco, Andrea
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.
Cyclization; Dioxanes, Dihydroquinolones
01 Pubblicazione su rivista::01a Articolo in rivista
One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids / Arcadi, Antonio; Calcaterra, Andrea; Fabrizi, Giancarlo; Fochetti, Andrea; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 20:15(2022), pp. 3160-3173. [10.1039/D2OB00289B]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1654400
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