Том 59, № 3 (2023)

The review describes in detail the methods of obtaining thiazolo[3,2- a ]pyrimidines, synthesis and chemical properties of 2-substituted derivatives of thiazolo[3,2- a ]pyrimidines, analysis of crystal structures of 2-arylmethylidene derivatives of thiazolo[3,2- a ]pyrimidines and demonstrates their high antitumor, antibacterial and anti-inflammatory activity.

The unexpected allylation of secondary phosphine sulfides with allyl sulfides has been found. The reaction proceeds under mild conditions (no catalyst and solvent, 80°C) to give allyldiorganylphosphine sulfides (yield up to 79%). The latter, under the reaction conditions, are able to add the initial secondary phosphine sulfides across the allyl group in the anti-Markovnikov mode to deliver propane-1,3-diylbis(diorganylphosphine sulfides), promising extractants of heavy metals and ligands for the synthesis of metal complex catalysts.

Racemic 1-(adamantan-1-yl)propan-1,2-diamine which was resolved with l-malic acid was obtained from trans-2-(adamantan-1-yl)-3-methylaziridine. The isolated (1 S ,2 R )-isomer was derivatized with benzyl. Enantiomeric excess of (2 S ,3 R )-2-(adamantan-1-yl)-3-methyl-5,6-diphenyl-2,3-dihydropyrazine was determined by HPLC. (4 S ,5 R )-4-(Adamantan-1-yl)-5-methylimidazolidine-2-thione was synthesized by the reaction of (1 S ,2 R )-diamine with carbon disulfide; absolute configuration was determined by X-ray diffraction analysis. Ligands were synthesized on the basis of racemic and chiral (1 S ,2 R )-1-(adamantan-1-yl)propan-1,2-diamines. The catalytic activity complexes were studied using Michael, Henri and epoxidation model reactions. For the model reaction of Henri stereodivergence was noted when using ligands of a similar structure.

The reaction of 1,3-dibromoadamantanes with fuming nitric acid gave the mixture of 2-oxaadamantane derivatives. In the same conditions 1,3-diiodoadamantanes gave the corresponding 1,3-dinitroxyadamantanes. A preparative method for the synthesis of 5,7-dimethyl-3-bromomethyl-1-hydroxy-2-oxaadamantan-1-ol from 5,7-dimethyl-1,3-dibromoadamantane was developed. The obtained compounds can be used in the directed synthesis of substances with high molecular complexity for studying of biological activity.

The first representatives of chiral ferrocenophanes based on bispidines have been synthesized. It is shown that their structure in solution is similar to the previously described achiral ferrocenophane.

A one-pot method for the synthesis of 3-carbomoyl-2-oxo-1,2-dihydropyridine-4-carboxylic acids has been developed, which consists in the interaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with water and the hydrolysis of the resulting mixture of 2-oxo-1, 2-dihydropyridine-3,4-dicarbonitrile and 2-oxo-4-cyano-1,2-dihydropyridine-3-carboxamide with sodium hydroxide solution.

N -Sulfinyltrifluoromethanesulfonamide reacts with succinyl chloride to form 1-[(trifluoromethyl)sulfonyl]pyrrolidine-2,5-dione in high yield. The structure of the product was proved by X-ray diffraction analysis. The product is opened with ethanol under mild conditions selectively at the C-N bond to form (1 E )-4-ethoxy-4oxo- N -[(trifluoromethyl)sulfonyl]butanimidic acid.