The article presents the results of a chemical study of semi-dry wormwood (Artemisia semiarida), an endemic plant of Kazakhstan. The amount of extractive substances was obtained by extraction with chloroform from air-dried crushed above-ground part of the plant collected in the vegetative phase. The compound was isolat-ed using a column chromatography method. Silica gel of the KSK brand was used with the ratio of the sum of substances – carrier = 1:10. When the column was eluted with a 13:7 petroleum ether – ethyl acetate mixture, a yellow crystalline substance of the composition C18H16O7 with m.p. 234–237 °C was obtained (recrystalli-zation from ethyl acetate). The structure of the obtained compound (5,7-dihydroxy-6,3′,4′-trimethoxyflavone or eupatilin) was established by analysis of IR and NMR spectra. The spatial structure of eupatilin was de-termined by X-ray diffraction. In the crystal structure of 5,7-dihydroxy-6,3′,4′-trimethoxyflavone the rotation of the phenyl ring relative to the main framework (chromene ring) was found to be only 4.1°. Four conform-ers with different rotations of the phenyl ring (the torsional angles of O1C2C1′C2′ are 30, 140, 210, and 320°, respectively) and small energy barriers (about 8.4 kJ/mol) can be realized in the free state of the molecule.

The article presents results on the synthesis and investigation of the structural features of a number of 1,4-disubstituted 1H-1,2,3-triazole derivatives of the alkaloid lupinine. Lupinine modification reactions were carried out at the hydroxymethylene group in the C-1 position of the quinolysine backbone. It has been shown that (octahydro-2H-quinolysine-1-ylmethyl)methanesulfonate in high yield (93%) is formed by the interaction of lupinine with methanesulfonyl chloride in methylene chloride. Subsequent treatment of this compound with sodium azide in dimethylformamide on heating leads to the formation of 1-(azidomethyl)octahydro-2H-quinolysine in 61% yield. It has been found that the reaction of a new azide with terminal alkynes of various nature in the presence of aqueous СuSO4 and sodium ascorbate in dimethylformamide can form the corresponding 4-substituted (1S,9aR)-1-[(1,2,3-triazol-1-yl)methyl]octahydro-1H-quinolysines. 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 high selectivity of the reaction is explained by the action mechanism of the Sharpless catalyst. The spatial structure of the molecules of lupinine methanesulfonate, 4-aryltriazolylmethyl-octahydro-quinolysines has been established by X-ray diffraction analysis. X-ray structural analysis data of new compounds have been deposited in the form of CIF files at the Cambridge Crystallographic Data Center.

There has been presented data on the synthesis of monoamides and cyclic imides which are derivatives of isonicotinic acid hydrazide. Cyclic anhydrides of carboxylic acids (succinic, maleic and phthalic) easily react with the hydrazide of isonicotinic acid with cycle opening, forming isonicotinoylhydrazide of dicarboxylic acids, and under more severe conditions the latter are transformed into cyclic acid imides. The structures of the synthesized compounds were studied using 1H- and 13C-NMR spectroscopy, as well as data from twodimensional COSY (1H-1H) and HMQC (1H-13C) spectra. The values of chemical shifts, multiplicity and integral intensity of 1H and 13C signals in one-dimensional NMR spectra were determined. Homo- and heteronuclear interactions confirming the structure of the studied compounds were established using spectra in the COSY (1H-1H) and HMQC (1H-13C) formats. In the approximation of the density functional B3LYP with a base set of 6-31G(d), the enthalpy of the reactions ΔHr in the absence and in the presence of a solvent — isopropanol (self-consistent reaction field method) were calculated quantum-chemically.

For the first time, synthesis of 8-formylharmine by the Vilsmeier reaction was carried out. 8-Formylharmine was obtained by treating alkaloid harmine with dichloromethoxymethane in the presence of SnCl4.The yield of the target product was 64 %. The structure of the obtained compound was established on the basis of 1H and 13C NMR spectroscopy as well as mass-spectrometry data. The crystalline structure of 8-formylharmine was determined by X-ray diffraction. It has been shown that the replacement of the hydrogen atom in the harmine molecule with a formyl group occurs at the C8 atom. It was revealed that the methoxy group at the C7 atom changes its orientation to the opposite one as compared to the orientation in the harmine molecule and its salts due to the mutual Van der Waals repulsion of the methoxy and formyl groups. A weak intramolecular hydrogen bond was found in the crystal between the O2 atom of the formyl group and the hydrogen atom of the secondary amino group. It was shown that molecules in the crystal form an intermolecular hydrogen bond between the same atoms (О2 and НN9A), as a result of which dimers are formed.

(E)-1-(2-(4-bromobutoxy)-6-hydroxy-4-methoxyphenyl-3-phenylprop-2-en-1-one was synthesized from the pinostrobin molecule. The tetrahydropyran cycle was opened in acetone under heating (50–60 °C) mixtures of components for 16 hours in the presence of 3 moles of K2CO3 and 1,4-dibromobutane. The resulting sub-stance is a yellow powder of the composition C20H21BrO4, mp 83.7–86.6 °C. The structure of the obtained compound was established on the basis of the data of elemental analysis, IR and NMR spectra. As a result of X-ray diffraction analysis, it was found that the hydrogen atoms in the C8=C9 bond take the trans-conformation. The rotation of the С1…С6 phenyl ring (flat with an accuracy of ±0.008 Å) relative to the С10…С15 cycle (flat with an accuracy of ±0.004 Å) is 14.3°. In the crystal, the molecules are linked by an intramolecular hydrogen bond O4-H....O1 (distances O-H 0.95(8) Ǻ, O····O 2.469(6) Ǻ, H····O 1.58 (8) Ǻ, angle O-H····O 153(7)°). The formation of (E)-1-(2-(4-bromobutoxy)-6-hydroxy-4-methoxy-1-phenylprop-2-en-1-one can be explained by the ease of the retro-Michael reaction of the pyran ring and the subsequent O-alkylation of the resulting chalcone. Carrying out the reaction in the presence of other bases (cesium car-bonate, triethylamine) did not lead to success. The starting substance (pinostrobin) was completely converted into oligomeric compounds.