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-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.
Green Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, Italy. serena.gabrielli@unicam.it.
Serena
S
Gabrielli
Green Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, Italy. alessand.giardinieri@studenti.unicam.it.
Alessandra
A
Giardinieri
Green Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, Italy. susanna.sampaolesi@unicam.it.
Susanna
S
Sampaolesi
Green Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, Italy. roberto.ballini@unicam.it.
Roberto
R
Ballini
Green Chemistry Group, Chemistry Division, School of Science and Technology, University of Camerino, via S. Agostino 1, 62032 Camerino, Italy. alessandro.palmieri@unicam.it.
Alessandro
A
Palmieri
D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry; D008024:Ligands; D008670:Metals / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*
D002264:Carboxylic Acids; D006573:Heterocyclic Compounds, 1-Ring; D008024:Ligands; D008670:Metals; D009943:Organophosphorus Compounds; D011804:Quinolines; C116638:BEMP phosphazene
heterocycles; one-pot processes; quinolines; solid supported reagents; β-nitroacrylates