Structural study of 8-azole derivatives of protoberberine alkaloids: experimental and quantum chemical approach
| Authors | |
|---|---|
| Year of publication | 2010 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| 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. |
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