Academic Journal
One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids
| العنوان: | One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids |
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| المؤلفون: | Arcadi, Antonio, Calcaterra, Andrea, Fabrizi, Giancarlo, Fochetti, Andrea, Goggiamani, Antonella, Iazzetti, Antonia, Marrone, Federico, Mazzoccanti, Giulia, Serraiocco, Andrea |
| المساهمون: | Arcadi, Antonio, Calcaterra, Andrea, Fabrizi, Giancarlo, Fochetti, Andrea, Goggiamani, Antonella, Iazzetti, Antonia, Marrone, Federico, Mazzoccanti, Giulia, Serraiocco, Andrea |
| سنة النشر: | 2022 |
| المجموعة: | Sapienza Università di Roma: CINECA IRIS |
| مصطلحات موضوعية: | Cyclization, Dioxanes, Dihydroquinolones |
| الوصف: | 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. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| Relation: | info:eu-repo/semantics/altIdentifier/wos/WOS:000773645900001; volume:20; issue:15; firstpage:3160; lastpage:3173; numberofpages:14; journal:ORGANIC & BIOMOLECULAR CHEMISTRY; http://hdl.handle.net/11573/1654400; info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85128383867 |
| DOI: | 10.1039/D2OB00289B |
| الاتاحة: | http://hdl.handle.net/11573/1654400 https://doi.org/10.1039/D2OB00289B |
| رقم الانضمام: | edsbas.545E90C6 |
| قاعدة البيانات: | BASE |
| DOI: | 10.1039/D2OB00289B |
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