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Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1-3, 612 42 Brno, Czech Republic
Zentiva k.s., U kabelovny 130, 102 37 Prague 10, Czech Republic
Department of Chemistry of Natural Compounds, Faculty of Food and Biochemical Technology, Institute of Chemical Technology, Technicka 5, 166 28 Prague 6, Czech Republic
* Author to whom correspondence should be addressed.
Received: 20 July 2009; in revised form: 30 July 2009 / Accepted: 12 August 2009 / Published: 13 August 2009
Abstract: The conditions for the C-N bond forming reaction (C-N coupling reaction) between α-bromocarboxylate and nitrogen-containing non-aromatic heterocyclic rings under heterogeneous copper(I) oxide catalysis are investigated in this paper. All the generated compounds were fully characterized by IR, NMR and MS spectroscopy. Ab initio/DFT calculations of partial charges on nitrogen atoms in all the discussed heterocycles and on C(2) of carboxylate under applied conditions were predicted. These in silico results correlate relatively with the experimental observations.
Keywords: C-N nucleophilic coupling; N-heterocycles; ω-lactams; copper catalyst; ab initio/DFT calculations
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Brychtova, K.; Slaba, B.; Placek, L.; Jampilek, J.; Raich, I.; Csollei, J. Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles. Molecules 2009, 14, 3019-3029.
Brychtova K, Slaba B, Placek L, Jampilek J, Raich I, Csollei J. Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles. Molecules. 2009; 14(8):3019-3029.
Brychtova, Katerina; Slaba, Barbora; Placek, Lukas; Jampilek, Josef; Raich, Ivan; Csollei, Jozef. 2009. "Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles." Molecules 14, no. 8: 3019-3029.