A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions
Quinoline-2-carboxylates are an important subclass of quinoline derivatives largely present in a variety of biologically active molecules, as well as useful ligands in metal-catalyzed reactions. Herein, we present a new one-pot protocol for synthesizing this class of derivatives starting from β-nitr...
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MDPI AG
2016-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/6/776 |
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doaj-c30a49cede7546968bb5b2f54a0c0e312020-11-25T00:18:25ZengMDPI AGMolecules1420-30492016-06-0121677610.3390/molecules21060776molecules21060776A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous ConditionsSerena Gabrielli0Alessandra Giardinieri1Susanna Sampaolesi2Roberto Ballini3Alessandro Palmieri4Green Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, ItalyGreen Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, ItalyGreen Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, ItalyGreen Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, ItalyGreen Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, ItalyQuinoline-2-carboxylates are an important subclass of quinoline derivatives largely present in a variety of biologically active molecules, as well as useful ligands in metal-catalyzed reactions. Herein, we present a new one-pot protocol for synthesizing this class of derivatives starting from β-nitroacrylates and 2-aminobenzaldehydes. In order to optimize the protocol, we investigated several reaction conditions, obtaining the best results using the 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) as solid base, in acetonitrile. Finally, we demonstrated the generality of our approach over several substrates which led to synthesize a plethora of functionalized quinolines-2-carboxylate derivatives in good overall yields.http://www.mdpi.com/1420-3049/21/6/776quinolinesβ-nitroacrylatesone-pot processessolid supported reagentsheterocycles |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Serena Gabrielli Alessandra Giardinieri Susanna Sampaolesi Roberto Ballini Alessandro Palmieri |
| spellingShingle |
Serena Gabrielli Alessandra Giardinieri Susanna Sampaolesi Roberto Ballini Alessandro Palmieri A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions Molecules quinolines β-nitroacrylates one-pot processes solid supported reagents heterocycles |
| author_facet |
Serena Gabrielli Alessandra Giardinieri Susanna Sampaolesi Roberto Ballini Alessandro Palmieri |
| author_sort |
Serena Gabrielli |
| title |
A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions |
| title_short |
A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions |
| title_full |
A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions |
| title_fullStr |
A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions |
| title_full_unstemmed |
A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions |
| title_sort |
new one-pot synthesis of quinoline-2-carboxylates under heterogeneous conditions |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2016-06-01 |
| description |
Quinoline-2-carboxylates are an important subclass of quinoline derivatives largely present in a variety of biologically active molecules, as well as useful ligands in metal-catalyzed reactions. Herein, we present a new one-pot protocol for synthesizing this class of derivatives starting from β-nitroacrylates and 2-aminobenzaldehydes. In order to optimize the protocol, we investigated several reaction conditions, obtaining the best results using the 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) as solid base, in acetonitrile. Finally, we demonstrated the generality of our approach over several substrates which led to synthesize a plethora of functionalized quinolines-2-carboxylate derivatives in good overall yields. |
| topic |
quinolines β-nitroacrylates one-pot processes solid supported reagents heterocycles |
| url |
http://www.mdpi.com/1420-3049/21/6/776 |
| work_keys_str_mv |
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