


卷 59, 编号 3 (2023)
Articles
Glavnyy redaktor zhurnala "Zhurnal organicheskoy khimii", akademik RAN Beletskaya Irina Petrovna (k 90-letiyu so dnya rozhdeniya)
Žurnal organičeskoj himii. 2023;59(3):283-284



Synthesis, chemocal properties and application of 2-substituted derivatives of thiazolo[3,2-a]pyrimidine
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):285-315



One-pot synthesis of N-acylethenyl4-acylethenyliminodihydroquinolines from 4-aminoquinoline and alkynones
摘要
One-pot chemo-, regio- and stereoselective synthesis of ( Z )- N -acylethenyl-4-( E )-[( Z )-acylethenyl]iminodihydroquinolines with high yields (66-98%) has been elaborated by the reaction between 4-aminoqiunoline and alkynones in the КОН/H2O/MeCN system.
Žurnal organičeskoj himii. 2023;59(3):316-322



Unexpectedly easy non-catalytic transfer of allyl group from allyl sulfides to secondary phosphine sulfides
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):323-328



Catalyst-free reactions of Schiff bases with cyanopropargyl alcohols: synthesis of functionalized 1,3-oxazolidines
摘要
Schiff bases react with cyanopropargylic alcohols (80°C, 10-12 h) in the absence of catalysts and solvents to afford functionalized 1,3-oxazolidines in up to 82% yield. The reaction proceeds through a cascade of transformations including the formation of a 1,3-dipolar intermediate via the addition of a neutral N -nucleophile to the activated triple bond, the proton transfer from the hydroxyl group to the carbanionic center of the intermediate, and the intramolecular attack of the carbonyl carbon of the Schiff base by the O -centered anion to close 1,3-oxazolidine cycle.
Žurnal organičeskoj himii. 2023;59(3):329-337



Synthesis of 1-(adamantan-1-yl)propan-1,2-diamine and chiral ligands based thereon
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):338-350



Synthesis of 5,7-dichloro-2-adamantanone
摘要
The reaction of 2-adamantanecarboxylic acid with an excess of chlorine in the presence of AlCl3 under heating gave 5,7-dichloro-2-adamantanecarboxylic acid. This product was sequentially introduced into the Curtius, deamination, and oxidation reactions to form 5,7-dichloro-2-adamantanone. The resulting product is a key substrate for synthesis of new substances and materials with a set of practically important properties, including both the synthesis of biologically active molecules and systems for chemiluminescent diagnostic methods.
Žurnal organičeskoj himii. 2023;59(3):351-357



Reactions of 1,3-dihaloadamantanes with nitric acid
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):358-365



Chemical transformations of 3-bromoethyl-5,7-dimethyl2-oxaadamantan-1-ol in sulfuric acid
摘要
The reactions of 3-bromomethyl-5,7-dimethyl-2-oxaadamantan-1-ol in a 96% acid medium both in the presence and in the absence of nucleophiles were studied. During the reactions a number of structural transformations of the 2-oxaadamantane cage take place. The possibility of obtaining 1,2,3-trisubstituted adamantanes is also presented. The structural features of new compounds are investigated using 2D NMR spectroscopy and XRD analysis. The obtained compounds can be used in the directed synthesis of a new cage heterocycles for studying of biological activity.
Žurnal organičeskoj himii. 2023;59(3):366-375



Synthesis of chiral bispidine-based macrocycles
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):376-381



Reactions of β-nitro-substituted 1H-benzo[f]chromenes and benzofurans with nucleophiles
摘要
A series of 3-alkoxy-2-nitro-2,3-dihydro-1 H -benzo[ f ]chromenes as a mixture of cis - and trans -isomers was obtained in the reaction of 2-nitro-1 H -benzo[ f ]chromenes with alcohols. The reaction with secondary cyclic amines and 3-amino-5,5-dimethylcyclohex-2-en-1-one proceeds trans -diastereoselectively to form Michael adducts of benzochromane structure. Conjugated addition involving anilines leads to (2-hydroxy-1-naphthyl) methyl-substituted β-nitroenamines. The nucleophilic dearomatization of 3-nitrobenzofurans under the action of primary aromatic amines was shown to involve sequential aza- and retro-oxa-Michael reactions. This reaction illustrates the high propensity of 3-nitrobenzofurans to open the furan cycle.
Žurnal organičeskoj himii. 2023;59(3):382-399



One-pot synthesis of 3-carbomoyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):400-404



Semicarbazones of acetyldihydropyrans: diastereoselective acetylene-based two-step synthesis
摘要
2-Acetyl-3,4-dihydropyrans (diastereoselectively synthesized from acetylene and aromatic ketones in a one synthetic operation) reacted with semicarbazide hydrochloride to stereoselectively form semicarbazones of E -configuration in up to 86% yield.
Žurnal organičeskoj himii. 2023;59(3):405-410



Reaction of N-sulfinyltrifluoromethanesulfonamide with succinyl chloride
摘要
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.
Žurnal organičeskoj himii. 2023;59(3):411-414


