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

Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti*, Federico Marrone, Giulia Mazzoccanti, Andrea Serraiocco

*Autore corrispondente per questo lavoro

Risultato della ricerca: Contributo in rivistaArticolo in rivista

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
Lingua originaleEnglish
pagine (da-a)3160-3173
Numero di pagine14
RivistaORGANIC & BIOMOLECULAR CHEMISTRY
DOI
Stato di pubblicazionePubblicato - 2022

Keywords

  • Cyclization
  • Dihydroquinolones
  • Dioxanes

Fingerprint

Entra nei temi di ricerca di 'One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids'. Insieme formano una fingerprint unica.

Cita questo