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

被引：0

作者：

Arcadi, Antonio ^{[1
]}

Calcaterra, Andrea ^{[2
]}

Fabrizi, Giancarlo ^{[2
]}

Fochetti, Andrea ^{[2
]}

Goggiamani, Antonella ^{[2
]}

Iazzetti, Antonia ^{[3
]}

Marrone, Federico ^{[2
]}

Mazzoccanti, Giulia ^{[2
]}

Serraiocco, Andrea ^{[2
]}

机构：

[1] Dipartimento di Ingegneria e Scienze dell'Informazione e Matematica, Università degli Studi di L'Aquila, Via Vetoio, AQ, Coppito,67100, Italy

[2] Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma, Sapienza, P.le A. Moro 5, Rome,00185, Italy

[3] Dipartimento di Scienze Biotecnologiche di base, Università Cattolica del Sacro Cuore, Cliniche Intensivologiche e Perioperatorie, L.go Francesco Vito 1, Rome,00168, Italy

来源：

Organic and Biomolecular Chemistry | 2022年 / 20卷 / 15期

关键词：

Positive ions;

D O I：

暂无

中图分类号：

O62 [有机化学]; TQ [化学工业];

学科分类号：

070303 ; 0817 ; 081704 ;

摘要：

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 The Royal Society of Chemistry.

引用

页码：3160 / 3173

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[1] 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
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (15) : 3160 - 3173
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