Covalent bonding of azoles to quaternary protoberberine alkaloids
| Authors | |
|---|---|
| Year of publication | 2008 |
| Type | Article in Periodical |
| Magazine / Source | Magnetic Resonance in Chemistry |
| MU Faculty or unit | |
| Citation | |
| Web | DOI: 10.1002/mrc.2325 |
| Doi | http://dx.doi.org/10.1002/mrc.2325 |
| Field | Organic chemistry |
| Keywords | NMR; 1H; 13C; 15N; berberine; palmatine; coptisine; protoberberine alkaloid; nucleophilic addition; X-ray diffraction |
| Attached files | |
| Description | Adducts of the quaternary protoberberine alkaloids (QPA) berberine, palmatine, and coptisine were prepared with nucleophiles derived from pyrrole, pyrazole, imidazole, and 1,2,4-triazole. The products, 8-substituted 7,8-dihydroprotoberberines, were identified by mass spectrometry and 1D and 2D NMR spectroscopy, including 1H-15N shift correlations at natural abundance. In addition, two adducts of QPA with chloroform and methanethiolate were characterized by using NMR data. Single-crystal X-ray structures of 8-pyrrolyl-7,8-dihydroberberine, 8-pyrazolyl-7,8-dihydroberberine, and 8-imidazolyl-7,8-dihydroberberine are also presented. |
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