INTERACTION OF LUPININE AZIDE WITH SUBSTITUTED ARYLACETYLENES

The article presents the results of studies on the synthesis and structural features of a number of disubstituted 1H-1,2,3-triazole derivatives of the lupinine alkaloid. The chemical transformation of the quinolysin backbone in the structure of the lupinin molecule was carried out by the hydroxymethylene group at position C-1. The reactions were carried out in several stages in a medium of various solvents. It has been shown that when lupinine interacts with methanesulfochloride in the presence of triethylamine, a mesylate derivative of lupinine is formed in methylene chloride. Subsequent treatment of this compound by the action of sodium azide in a dimethylformamide medium under heating leads to the formation of an azide derivative of lupinine with a yield of 67%. It was found that when azide interacts with functionally substituted aromatic acetylenes of various natures in the presence of aqueous copper sulfate and sodium ascorbate, corresponding 4-substituted aromatic triazole derivatives of lupinine can be formed in dimethylformamide. New 1,2,3-triazole derivatives of lupinine, containing various aryl substituents at the C-4 position of the triazole ring, have been obtained. The structure of the obtained compounds was established based on the analysis of the ¹H and ¹³C NMR spectra. Multiplicity of signals of new compounds in the ¹³C NMR spectra was determined from the spectra recorded in the J-modulation mode (JMOD). The assignment of signals in the spectra was carried out using various modern methods of correlation spectroscopy ¹H-¹H (COZY), and ¹H-¹³C (HMBC, HSQC). The values of chemical shifts, multiplicity and integral intensity of ¹H and ¹³C signals in one-dimensional NMR spectra are determined