One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids. Issue 15 (28th March 2022)

• Record Type: Journal Article
• Authors: Arcadi, Antonio; Calcaterra, Andrea; Fabrizi, Giancarlo; Fochetti, Andrea; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 15(2022)
• Page Start: 3160
• Page End: 3173
• Publication Date: 2022-03-28
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00289b
• Languages: English
• ISSNs: 1477-0520

Abstract

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 Meldrum's acid derivatives under mild basic conditions. 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(1 H )-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 .