Structural study of 8-azole derivatives of protoberberine alkaloids: experimental and quantum chemical approach

Warning

This publication doesn't include Faculty of Economics and Administration. It includes Faculty of Science. Official publication website can be found on muni.cz.

Authors	MAIER Lukáš ŠOLOMEK Tomáš PIPÍŠKA Matej KŘÍŽ Zdeněk NEČAS Marek MAREK Radek
Year of publication	2010
Type	Article in Periodical
Magazine / Source	Tetrahedron
MU Faculty or unit	Faculty of Science
Citation
Web	DOI: 10.1016/j.tet.2010.09.030
Field	Organic chemistry
Keywords	Barrier to rotation; Berberine; Low-temperature NMR spectroscopy; Nucleus-independent chemical shift; Palmatine; Theoretical calculations
Description	New derivatives of protoberberine alkaloids were prepared by nucleophilic addition of some azoles to the iminium functionality of the quaternary protoberberine alkaloids. Compounds were structurally characterized mainly by 1H and 13C NMR spectroscopy. Additionally, conformational behaviors of selected derivatives varying in bulkiness of the azole moiety have been investigated by low temperature NMR spectroscopy and quantum chemical calculations. Ring current effects of pyrrole and carbazole moieties on selected 1H NMR resonances have been characterized, visualized, and discussed.
Related projects:	Proteins in metabolism and interaction of organisms with the environment Biomolecular centre