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Vol 60, No 10 (2024)

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Articles

Selective Synthesis of Pyrazol-3-yl- and Pyrazol-5-ylphosphonates

Mitrofanov A.Y., Devnozashvili D.N., Beletskaya I.P.

Abstract

An approach to selective synthesis regioisomeric N-substituted pyrazolyl-3-yl- and pyrazol-5-ylphosphonates based on the reaction of aryl-substituted hydrazines with 3-oxoprop-1-yn-1-ylphosphonates has been developed.

Žurnal organičeskoj himii. 2024;60(10):1007-1016
pages 1007-1016 views

1-Hydro-1,10-phenanthrolinium perchlorate and 1,10-Dihydro-1,10-phenanthrolinium Perchlorate in the Reaction of Electrocatalytic Production of Molecular Hydrogen

Yudina A.D., Boykova T.V., Ganz O.Y., Klimaeva L.A., Ulyakina Y.V., Burmistrova A.A., Karpunina T.O., Okina E.V.

Abstract

Using the cyclic voltammetry method, the electrochemical and electrocatalytic properties for hydrogen evolution reaction of the 1-hydro-1,10-phenanthrolinium perchlorate (I) and 1,10-dihydro-1,10-phenanthrolinium perchlorate (II) in the presence of CF3COOH were studied. The presence of hydrogen atoms at nitrogen in heterocyclic compounds has a significant effect on the electrochemical properties and the efficiency of the electrocatalytic process. The transition from 1-hydro-1,10-phenanthrolinium perchlorate (I) to 1,10-dihydro-1,10-phenanthrolinium perchlorate (II) leads to an increase in the efficiency of the process (higher TOF and TON values), despite identical mechanisms. The DFT method was used to study the mechanisms of the processes taking place and identify key intermediates.

Žurnal organičeskoj himii. 2024;60(10):1017-1024
pages 1017-1024 views

Synthesis of New 3-Aminopropyl(ω-aminoalkoxy)trisiloxanes

Vasiliev A.B., Lukin A.V., Ivanova K.Y., Kuzmin M.V., Kolyamshin O.A., Mitrasov Y.N.

Abstract

A one-pot, two-stage method for the synthesis of new aminotrisiloxanes has been developed, which consists of the sequential reaction of diphenylsilanediol with 3-aminopropyltriethoxysilane and amino alcohols.The synthesized di-, tetra-, and hexaaminotrisiloxanes have broad potential for use in both organic and macromolecular chemistry, in particular, as effective silicon-containing cross-linking agents and modifiers of epoxy resins.

Žurnal organičeskoj himii. 2024;60(10):1025-1029
pages 1025-1029 views

The Sintesis and Antioxidant Activity of New bis-1,3,4-Oxadiazoles, bis-1,3,4-Thiadiazoles, and Their Derivatives

Dilanyan S.V., Buniatyan Z.M., Panosyan H.A.

Abstract

Bis-1,3,4-oxadiazoles and bis-1,3,4-thiadiazoles with aryl and alkyl linkers were synthesized. In order to increase their hydrophilicity and potential biological activity, pharmacophore electron-deficient groups (carboxylic, nitrile) were introduced into the molecule. Functionalized compounds revealed a new type of biological activity such as inhibition of lipid oxidation in the form of a decrease in the amount of MDA.

Žurnal organičeskoj himii. 2024;60(10):1030-1035
pages 1030-1035 views

Method for Synthesis of 2-{[(2z)-4-Aryl-2-hydroxy-4-oxobut-2-enoyl]amino}benzoic Acids

Gein V.L., Nazarets O.V., Romanova A.V., Bobrovskaya O.V., Mokrushin I.G.

Abstract

The reaction of methyl esters of aroylpyrovinic acids with 2-aminobenzoic (anthranilic) acid in glacial acetic acid in the presence of anhydrous sodium acetate was obtained 2-{[(2Z)-4-aryl-2-hydroxy-4-oxobut-2-enoyl]amino}benzoic acids. Using X-ray crystallography, their spatial structure was established.

Žurnal organičeskoj himii. 2024;60(10):1036-1042
pages 1036-1042 views

Synthesis of New N-[(4-N1-Arylamino)phenyl]-1H-pyrrole-2,5-diones

Kolyamshin O.A., Mitrasov Y.N., Danilov V.A., Pylchikova Y.Y.

Abstract

The interaction of N1-phenyl- and N1-(4-methoxyphenyl)phenylene-1,4-diamines with maleic anhydride produced the corresponding monoamides of maleic acid, cyclization of which in the presence of p-toluene sulfonic acid synthesized N-[4-(N1-phenylamino)- or N1-(4-methoxyphenylamino)]phenyl-1H-pyrrole-2,5-diones.

Žurnal organičeskoj himii. 2024;60(10):1043-1047
pages 1043-1047 views

Unusual Stereoselectivity in Elimination Reactions of Allylic Acetate Catalyzed by Pd(PPh3)4 in (±)-9α,11α,15α-triacetate Cloprostenol p-Methoxybenzyl Ester

Zagitov V.V., Vostrikov N.S., Miftakhov M.S.

Abstract

Attempts to replace the allylic C15-acetate group of cloprostenol with a tosyl group under phase-transfer catalysis conditions (СH2Cl2/H2O, R3R′N+Hal-, NaOH, TsOH, Pd(PPh3)4) led to the corresponding 13E, 15Z derivative with moderate yield. The same compound is stereoselectivity formed in high yield when this reaction is carried out in a THF-Pd(PPh3)4-NaH medium.

Žurnal organičeskoj himii. 2024;60(10):1048-1053
pages 1048-1053 views

Quantum Chemical Study of Organic Reactions Mechanisms. XIII. The Reaction of Propargyl Chloride with Potassium 1,2-Ethandithiolate in the System Hydrazine Hydrate–KOH: Heterocyclization Paths

Chirkina E.A., Grabelnykh V.A., Korchevin N.A., Krivdin L.B., Rosenzweig I.B.

Abstract

Quantum chemical modeling of the mechanism of interaction of propargyl chloride with potassium 1,2-ethanedithiolate in the hydrazine hydrate–KOH system was carried out using the combined approach CCSD(T)/6-31+G*//B3LYP/6-311++G**. The elementary stages of the reaction and possible routes for the heterocyclization of the initial intermediates have been found. Under experimental conditions at a reaction temperature of 40-42°C, 6 hours, 2-methyl-5,6-dihydro-1,4-dithiine was obtained with a yield of 25% and 4,7-dithiadecadiine-2,8 with a yield of 24%. At a temperature of –10 ÷ –15°С, cyclic products are not formed.

Žurnal organičeskoj himii. 2024;60(10):1054-1069
pages 1054-1069 views

Interaction of 5-Hydroxypyrazolidine with Thiol-Containing Hydrazides as a Method of Synthesis of Biologically Active Ligands of Gold Glyco-Nanoparticles

Ershov A.Y., Martynenkov A.A., Lagoda I.V., Batyrenko A.A.

Abstract

The interaction of (3S)-1-acetyl-5-hydroxy-2-phenyl-3-methylpyrazolidine with 6-mercaptohexanoic and 11-mercaptoundecanoic acid hydrazides leads to the formation in 60–65% yields of (3S)-1-acetyl-5-[(ω-mercaptoacyl)hydrazine]-2-phenyl-3-methylpyrazolidines as a promising сo-ligands for the production of gold glyco-nanoparticles for biomedical purposes.

Žurnal organičeskoj himii. 2024;60(10):1070-1073
pages 1070-1073 views

A Simple Method for the Synthesis of Pyrazolo[1,2-c]benzo-1,3,4-thiadiazepine Derivatives Based on Formaldehyde, Acrolein, and 2-Mercaptobenzoic Acid Hydrazide

Ershov A.Y., Lagoda I.V., Batyrenko A.A., Martynenkov A.A.

Abstract

Based on 2-mercaptobenzoic acid hydrazide and commercially available formaldehyde and acrolein, a two-step method for the synthesis of a previously unknown 1-hydroxy-2,3-dihydropyrazolo[1,2-c]benzo-1,3,4-thiadiazepin-11(5H)-one, as a compound with a targeted antitumor effect, as well as a promising bioactive co-ligand for obtaining of gold glyco-nanoparticles for the biomedical purposes was developed

Žurnal organičeskoj himii. 2024;60(10):1074-1077
pages 1074-1077 views

Application of the ANRORC-Process for the Directional Synthesis of 5-Ureido-2-Pyrazolines as a Biologically Active Co-Ligand of Gold Glyconanoparticles

Ershov A.Y., Martynenkov A.A., Lagoda I.V., Batyrenko A.A.

Abstract

Interaction of 1-phenyl-4,6-dimethylpyrimidine-2(1H)-one with 4-mercaptobuturic acid hydrazide proceeds as ANRORC (Addition of the Nucleophile–Ring Opening–Ring Closure) process and gives in the formation with 60% yield of 1-(4-mercaptobutanoyl)-3,5-dimethyl-5-(3-phenylcarbamoylamino)-2-pyrazoline as promising сo-ligand for the preparation of gold glyconanoparticles for biomedical purposes.

Žurnal organičeskoj himii. 2024;60(10):1078-1081
pages 1078-1081 views

Synthesis of Ppolyfunctional [1,2′-Bipyridine]-1-ium Chlorides

Tutkin P.I., Ershova A.I., Karpov S.V., Andreeva V.V., Ershov O.V.

Abstract

A method has been developed for the preparation of polyfunctional pyridine derivatives — 6′-amino-4′-aryl-3′,5′-dicyano-[1,2′-bipyridine]-1-ium chlorides based on simple precursors of malononitrile and aldehydes.

Žurnal organičeskoj himii. 2024;60(10):1082-1086
pages 1082-1086 views