title: Coupling reactions of alpha-bromocarboxylate with non-aromatic N-heterocycles.
abstract: The conditions for the C-N bond forming reaction (C-N coupling reaction) between alpha-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.
authors.affiliation: Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1-3, 612 42 Brno, Czech Republic. brychtovak@vfu.cz
authors.forename: Katerina
authors.initials: K
authors.lastname: Brychtova
authors.forename: Barbora
authors.initials: B
authors.lastname: Slaba
authors.forename: Lukas
authors.initials: L
authors.lastname: Placek
authors.forename: Josef
authors.initials: J
authors.lastname: Jampilek
authors.forename: Ivan
authors.initials: I
authors.lastname: Raich
authors.forename: Jozef
authors.initials: J
authors.lastname: Csollei
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
chemical_list: D006571:Heterocyclic Compounds; D003300:Copper; C030973:cupric oxide
references.citation: Pharmazie. 2000 Oct;55(10):759-61
references.pmid: 11082838
references.citation: J Org Chem. 1972 Dec 29;37(26):4396-9
references.pmid: 4642614
references.citation: J Pharm Pharmacol. 2005 Nov;57(11):1389-96
references.pmid: 16259770
references.citation: Adv Drug Deliv Rev. 2004 Mar 27;56(5):603-18
references.pmid: 15019749
references.citation: J Am Chem Soc. 1948 Nov;70(11):3626
references.pmid: 18121882
references.citation: Science. 2000 Mar 17;287(5460):1964-9
references.pmid: 10720315
references.citation: Drug Dev Ind Pharm. 2000 Nov;26(11):1131-40
references.pmid: 11068686
references.citation: Chem Rev. 2008 Aug;108(8):3054-131
references.pmid: 18698737