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  • A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions.

A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions.

Molecules (Basel, Switzerland) (2016-06-18)
Serena Gabrielli, Alessandra Giardinieri, Susanna Sampaolesi, Roberto Ballini, Alessandro Palmieri
ABSTRACT

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.

MATERIALS
Product Number
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Product Description

Sigma-Aldrich
2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine, polymer-bound, 200-400 mesh, extent of labeling: 2.0-2.5 mmol/g loading, 1 % cross-linked