NITRATION REACTION OF THE QUINOLINE ALKALOID HAPLOPHYLLIDINE
Abstract
Alkaloids with a quinoline substructure are widespread and possess different biologically activities.For example, carteolol are used to treat arrhythmia and glaucoma, rosoxacin is used to treat respiratory tract, urinary tract and bacterial infections.In order to obtain a new alkaloid derivative nitration reaction was carriedout on the basis of haplophyllidine (1), a quinoline alkaloid isolated from the seeds ofthe Haplophyllum perforatum.The haplophyllidine alkaloid was dissolved in acetic anhydride and concentrated HNO3 was added dropwise over half an hour at a temperature of 0-5℃.The reaction was then carried out at room temperature for 5 hours.As a result of the reaction, an nitro ester of haplophyllidine (2) was formed inyield of 76%.The structure of the product is confirmed by 1 H and 13 C NMR spectroscopy and X-ray diffraction analysis.