Vol 59, No 11 (2023)

The reaction of triflamide with allyl cyanide in benzonitrile and isobutyronitrile solutions in the presence of NBS has been studied. In both cases, the corresponding amidines - the products of the solvent incorporation are formed. In benzonitrile, depending on the reaction conditions, the isomeric N -(2-bromo-3-cyanopropyl)- N '-(triflyl)benzamidine and N -(1-bromo-3-cyanoprop-2-yl)- N '-(triflyl)benzamidine were obtained in various ratio. From the reaction in isobutyronitrile, N -(2-bromo-3-cyanopropyl)- N '-(triflyl)isobutyramidine and the product of diamination, N -[3-cyano-1-(triflamido)propyl]isobutyramide were isolated.

The 1,3-dipolar cycloaddition of 1 H -pyrrole-2,3-diones to azomethine ylides obtained in situ by the condensation of L-proline and arylcarbaldehydes proceeds regio- and diastereoselectively and leads to the formation of substituted ethyl 1,2,5',6',7',7a'-hexahydro-3' H -spiro[pyrrole-3,2'-pyrrolo[2,1- b ]oxazole]-4-carboxylates. The structure of one of the obtained compounds was confirmed by single crystal X-ray analysis.

By the reaction of 1-(3,4-dimethoxy)phenylcycloalkanmethan- and 4-(3,4-dimethoxyphenyl)tetrahydropyran-4-methanamines with benzo[ d ][1,3]dioxol-5-carbonyl chloride corresponding N -substituted benzo[ d ][1,3]dioxol-5-carboxamides were synthesized. Cyclization of the latter with phosphorus oxychloride gave dihydroisoquinolines reduced with sodium borohydride to the corresponding spiro-substituted tetrahydroisoquinolines, whose methylation according to Eschweiler-Clark reaction gave N -methyl derivatives. By condensation abovementioned amines with benzo[ d ][1,3]dioxol-5-carbaldehyde Schiff bases were synthesized. The reduction of the latter with sodium borohydride gave the corresponding secondary amines - non-cyclic analogues of tetrahydroisoquinolines, which undergo cyclization under the conditions of the Eschweiler-Clark reaction to form N -benzodioxolmethyl-substituted tetrahydroisoquinolines.

The synthesis was carried out and the transformations of 1-aryladamantanes in fuming nitric acid were studied. The reactions include nitroxylation of saturated cage and nitration of the aromatic moiety and lead to 3-(dinitroaryl)-1-adamantylnitrates. A number of new polyfunctional compounds have been synthesized based on reactions of substituted 3-(dinitroaryl)-1-adamantyl nitrates with nucleophiles in concentrated sulfuric acid. Due to the multifunctionality, the obtained compounds can be used as starting materials in the synthesis of substances with a wide spectrum of biological activity and materials with a complex of valuable properties.

The possibility of conjugate electroreduction of carbon dioxide and hydrogen in the presence of 2,2'-bipyridine and its N -substituted salts in the presence of acids with different pKa values was studied. It was revealed how the strength of the acid affects the efficiency of the process; in particular, it was determined that the presence of methylsulfonic acid in the system promotes the conjugate formation of hydrogen and the reduction of carbon dioxide to formic acid. Probable mechanisms for the reactions occurring have been proposed.

The charges on the reaction centers of 2-amino-4-methylthiazole and 5-aminotetrazole, which predetermine their interaction with tropylium tetrafluoroborate, were determined by quantum chemical calculation (AM1) in accordance with the charge control of the process. New compounds 4-methyl-5-(cyclohepta-1¹,3¹,5¹-trienyl)-2-aminothiazole and 5-( N , N -dicyclohepta-1¹,3¹,5¹-trienyl)aminotetrazole were obtained.

The dipeptide glycyl-( S )-5-hydroxynorvaline was obtained from 1- tert -butyl 5-methyl N -Boc-glycyl-( S )-glutamate as a result of saponification and subsequent reduction of the activated 5-carboxyl group with sodium borohydride followed by removal of the N -Boc and OBu ^t protecting groups by refluxing in a dioxane-water mixture. Using the example of the synthesis of ( S )-5-hydroxynorvaline, it has been shown that the used sequence of chemical transformations is not accompanied by racemization.