JournalTOCs

Russian Journal of Organic Chemistry
Journal Prestige (SJR): 0.246

Citation Impact (citeScore): 1
Number of Followers: 3

Hybrid journal (It can contain Open Access articles)
ISSN (Print) 1608-3393 - ISSN (Online) 1070-4280
Published by Springer-Verlag

[2468 journals]

Enantioselective Aminomethylation of 1-(Benzyloxy)propan-2-one with
3-[(Pent-2-yn-1-yl)oxy]aniline
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  Abstract: Enantioselective aminomethylation of 1-(benzyloxy)propan-2-one with 3-[(pent-2-yn-1-yl)oxy]aniline and aliphatic aldehydes in the presence of pseudoephedrine as a chiral catalyst afforded the corresponding Mannich type condensation products as mixtures of (3R,4R) and (3R,4S) diastereoisomers at ratios of 3:1 to 5:1 in 57–63% yields with a high diastereoisomer excess.
  PubDate: 2023-06-01
Synthesis of Some Nucleoside Analogs via Mannich Reaction of Benzimidazole
and Imidazoline Derivatives and Their Characterization as Potential
Antimicrobial Agents
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  Abstract: The condensation of ethylenediamine or o-phenylenediamine with benzaldehyde or p-bromobenzaldehyde, respectively, gave the corresponding imidazoline or benzimidazole derivative which was subjected to Mannich aminomethylation to produce new nucleobase analogs. α-D-Glucose was converted to peracetyl derivative, followed by treatment with HBr in acetic acid to obtain 1-bromo sugar. Condensation of the latter with nucleobases afforded new protected nucleoside analogs which were hydrolyzed with sodium methoxide in methanol to obtain free nucleoside analogs. The synthesized compounds were identified by FT-IR and 1H and 13C NMR spectroscopy, and their in vitro antimicrobial activity against four types of bacteria and fungi was evaluated.
  PubDate: 2023-06-01
Synergistic Effects of Cyclic Ketals in Fuel Compositions and
Antibacterial Agents
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  Abstract: A synergistic effect of cyclic ketals in compositions with lower alcohols has been revealed for the first time while adding those ketals to alcohol-containing gasoline. By using model oxidation reactions of ketals and their structural analogs, 1,3-benzodioxolanes, in protic media, the synergistic effect was rationalized assuming the formation of ketal–alcohol complexes possessing surfactant properties, which give rise to hydrated supramolecular structures around them. Deactivation of hot radicals with the transition from the explosive combustion mode to stationary combustion inside these structures is more effective than in the bulk medium. Such structuring effect is general for the behavior of ketals in hydrophobic–hydrophilic systems, including biological ones. This conclusion has been confirmed by studying the activity of cyclic ketals in compositions with antibacterial agents, as well as with alcohols and carboxylic acids.
  PubDate: 2023-06-01
Synthesis of 4,5-Dihydro-1,2-oxazoles and 1,2-Oxazole Containing Uracil
Fragments
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  Abstract: 1,3-Dipolar cycloaddition of allylic compounds or propargyl alcohol to nitrile oxide generated from 6-methyluracil-5-carboximidoyl chloride afforded a series of 4,5-dihydro-1,2-oxazoles and 1,2-oxazole containing uracil fragments.
  PubDate: 2023-06-01
Synthesis of 5-Chloro-3-styryl-1H-pyrazoles Based on 2,2-Dichlorovinyl
Ketones
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  Abstract: The condensation of 4,4-dichlorobut-3-en-2-one with aromatic aldehydes in the presence of a catalytic amount of sulfuric acid afforded 1,1-dichloro-5-(4-R-phenyl)penta-1,4-dien-3-ones which reacted with substituted hydrazines under mild conditions in chemo- and regioselective fashion to give 3-[(E)-2-arylethenyl]-5-chloro-1-methyl-1H-pyrazoles in up to 81% yield. The reaction of 4-bromo-1,1-dichloro-5-(4-methoxyphenyl)penta-1,4-dien-3-one with N,N-dimethylhydrazine produced 3-[1-bromo-2-(4-methoxyphenyl)ethenyl]-5-chloro-1-methyl-1H-pyrazole which was converted to 5-chloro-3-[(4-methoxyphenyl)ethynyl]-1-methyl-1H-pyrazole in 69% yield on heating in DMSO in the presence of KF at 120°C. The structure of the synthesized compounds was confirmed by IR, NMR, and mass spectra and elemental analyses.
  PubDate: 2023-06-01
Transformations of Seven-Membered Terpene Lactones toward
Low-Molecular-Weight Bioregulators
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  Abstract: The review describes low-temperature reduction of (–)-mentholactone with diisobutylaluminum hydride in methylene chloride. Depending on the conditions, three products are formed: (2S,4R,7S)-7-isopropyl-4-methyloxepan-2-ol [(–)-mentholactol), (6R)-8-hydroxy-2,6-dimethyloctan-3-one, and (2S,4R,7S)-2-isobutoxy-7-isopropyl-4-methyloxepane. Possible ways of formation of each product have been proposed, and conditions for their selective formation have been found. The synthesis of oxepan-2-ol isobutyl acetals via low-temperature (–70°C) reduction of 7-membered lactones with diisobutylaluminum hydride in methylene chloride is considered. The synthesis of a number of low-molecular-weight bioregulators, including optically active pheromones of insect pests in agriculture and forestry, based on (–)-mentholactol, its aluminate, and (6R)-8-hydroxy-2,6-dimethyloctan-3-one is discussed.
  PubDate: 2023-06-01
A Novel Synthesis of 2-Quinolinyl Chromones Using Grinding Technique under
Solvent-Free Conditions
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  Abstract: A simple, efficient, and eco-friendly procedure for the synthesis of 2-quinolinyl chromones via oxidative cyclization of 2-hydroxyquinolinyl chalcones by grinding with ammonium iodide at room temperature under solvent-free conditions has been described. The protocol is very efficient as the reactions are carried out at room temperature with high yields and avoid the use of hazardous chemicals and organic solvents at any stage of the reaction.
  PubDate: 2023-06-01
Synthesis of
4-{4-[(Alkylsulfanyl)methyl]-3,5-dimethyl-1H-pyrazole-1-carbonyl}pyridines
from 3-[(Alkylsulfanyl)methyl]pentane-2,4-diones
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  Abstract: Heterocyclization of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with isonicotinic acid hydrazide in ethanol in the presence of a catalytic amount of aqueous HCl under microwave irradiation or without it afforded new 4-{4-[(alkylsulfanyl)methyl]-3,5-dimethyl-1H-pyrazole-1-carbonyl)pyridines. 3-[(Alkanesulfonyl)methyl]pentane-2,4-diones under similar conditions were converted to the corresponding 4-[(alkanesulfonyl)methyl]-3,5-dimethyl-1H-pyrazoles.
  PubDate: 2023-06-01
New Syntheses of Cycloalka[c]pyridine-3-carboxamide and -carbonitrile
Derivatives
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  Abstract: Nicotinamide and nicotinonitrile derivatives containing a C5–C7-cycloalkane ring fused to the C4–C5 bond were synthesized via Knoevenagel condensation, nucleophilic vinylic substitution (SNVin), and alkylation. The structure of (1-amino-5-phenyl-5,6,7,8-tetrahydrothieno[2,3-c]isoquinolin-2-yl)(phenyl)methanone was determined by X-ray analysis.
  PubDate: 2023-06-01
Copper(I)-Catalyzed Regioselective Synthesis of
1,2,3-Triazole–Phthalazine-1,4-dione Hybrids, and Their Anticancer and
Molecular Docking Studies
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  Abstract: A new series of phthalazine-based 1,2,3-triazole derivatives were synthesized by the copper-catalyzed azide–alkyne cycloaddition of 2-phenyl-3-(prop-2-yn-1-yl)-2,3-dihydrophthalazine-1,4-dione and substituted phenyl azides. The synthesized compounds were evaluated for their in vitro anticancer activity against three human cancer cell lines, namely A375, A549, and MCF-7 using an MTT assay, and IC50 values of 2.33±0.43, 7.21±0.61, and 3.96±0.41 µM, respectively, were found for the most active compounds. In particular, 2-{[1-(4-nitrophenyl)-1H-1,2,3-triazole-4-yl]methyl}-3-phenyl-2,3-dihydrophthalazine-1,4-dione (6e) showed promising activity, and molecular docking study was performed for this compound with respect to the EGFR.
  PubDate: 2023-06-01
Synthesis and Antimicrobial Activity of Novel
(1-Aryl-1H-1,2,3-triazol-4-yl)methyl
3-Acetamido-1-phenyl-1H-benzo[f]chromene-2-carboxylates
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  Abstract: A series of novel (1-aryl-1H-1,2,3-triazol-4-yl)methyl 3-acetamido-1-phenyl-1H-benzo[f]chromene-2-carboxylates were synthesized from prop-2-yn-1-yl 3-acetamido-1-phenyl-1H-benzo[f]chromene-2-carboxylate. 3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile and 2-amino-4-phenyl-4a,5,6,7,8,8a-hexahydro-4H-chromene-3-carbonitrile were prepared by three-component condensation of benzaldehyde, β-naphthol or cyclohexanol, and malononitrile. The synthesized compounds were evaluated for their antibacterial and antifungal activities in comparison to chloramphenicol and amphotericin B as reference antibiotics.
  PubDate: 2023-06-01
Synthesis of Indolo[2,3-b]quinolines via a Visible Light-Induced
Intramolecular Oxidative Cyclization and Detosylation
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  Abstract: A transition metal-free, visible light-induced intramolecular oxidative cylclization–detosylation–aromatization was discovered. This photocatalytic strategy generated potentially bioactive indolo[2,3-b]quinoline derivatives in up to 97% yield. With a simple setup, this protocol works efficiently under mild conditions. The final products were obtained both in the presence and in the absence of Eosin Y sodium salt, but the reaction efficiency was largely improved with the use of a photosensitizer.
  PubDate: 2023-06-01
A Simple and Convenient Synthesis of Dibutyl (13C)Carbonate
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  Abstract: The reaction of butyl iodide with silver (13C)carbonate prepared from available barium (13C)carbonate afforded dibutyl (13C)carbonate in high yield via a simple and convenient laboratory procedure.
  PubDate: 2023-06-01
Synthesis of 16-Nitro- and 16-Amino-14,17-ethanoestrane Derivatives
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  Abstract: The hydrogenation of 16-nitro-14,17-etheno steroids has been studied using different catalysts. The chemoselectivity criteria have been established, and new bridged estradiol analogs containing nitro, amino, and hydroxyamino groups on the D ring have been obtained. Complete signal assignment in the NMR spectra of the synthesized compounds has been performed.
  PubDate: 2023-06-01
New Quinolin-2-one, Indazole, and Benzisoxazole Derivatives Derived from
Chalcones: Synthesis, Characterization, and Biological Activity
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  Abstract: New quinolin-2-one, indazole, and benzisoxazole derivatives were synthesized starting from chalcones. The synthesized compounds were characterized by elemental analyses, FTIR, 1H NMR, and mass spectra and evaluated for antibacterial and antifungal activities against Escherichia coli, Bacillus subtilis, and Candida albicans.
  PubDate: 2023-06-01
Electrochemical Aspect of the Synthesis of 2-Nitroethanol-Based
Heteroarchitecture
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  Abstract: The compatibility of several functional groups appeared much tapered in classical coupling organic reaction due to the use of strong bases, organic solvents, and reagents. Therefore, an innovative electrochemical strategy of activating an acidic hydrogen in the ethanol/lithium perchlorate system has been described to accomplish the criteria of ecological footprint for the synthesis of 2-nitroethanol-based heteroarchitecture. This innovative protocol is simple and clean, and it sets the stage for designing molecular hydrogen via in situ electrogenerated base (EGBS). After screening different solvents, it has been found that the ethanol/lithium perchlorate electrolyte system has unleashed power that indirectly activates an acidic hydrogen in an active methylene compound. For clarity, a concise study has been performed on dissociation constant value and its effect on redox potential that is stimulated indirectly through electrical input. This tactic offers several advantages such as a cleaner reaction profile, shorter reaction time, simple workup procedure, and excellent yield.
  PubDate: 2023-06-01
Recyclization of 5-Substituted 4-(2,2,2-Trichloroacetyl)furan-2,3-diones
with (Het)Arenecarbohydrazides
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  Abstract: The reaction of 5-substituted 4-(2,2,2-trichloroacetyl)furan-2,3-diones with substituted benzohydrazides, thiophene-2-carbohydrazide, or 2-phenylacetohydrazide in anhydrous chloroform on stirring for several hours afforded 1-substituted 3-aryl(heteroaryl)-5-hydroxy-4-(2,2,2-trichloroacetyl)-4,5-dihydro-1H-pyrazole5-carboxylic acids as mixtures of two diastereoisomers at a ratio of about 70:30.
  PubDate: 2023-06-01
Mass Spectra of New Heterocycles: XXV. Electron Ionization Study of
N-[5-Aminothiophen-2-yl]thioureas
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  Abstract: The electron ionization mass spectra of previously unknown N-(5-aminothiophen-2-yl)thioureas obtained in one preparative step from propargylamines and isothiocyanates were studied for the first time, and the main fragmentation patterns of these compounds were revealed. All the thienylthioureas studied form a molecular ion (Irel 7–61%), whose common fragmentation pathway {except for N-[5-(diethylamino)thiophen-2-yl]-N,N'-diphenylthiourea} is the cleavage of the R1N–C(=S) bond to form an intense [M – R2NHCS]+ ion peak (Irel 35–85%). The main fragmentation pathway of the molecular ions of N-[5-(diethylamino)thiophen-2-yl]-N,N'-diphenylthiourea is associated with the opening of the thiophene ring by the C2–S and C4–C5 bonds. N-[5-(Pyrrolidin-1-yl)thiophen-2-yl]- and N-[5-(piperidin-1-yl)thiophen-2-yl]thioureas characteristically undergo intense specific rearrangements that reveal themselves in the occurrence of unexpected primary fragmentation pathways of the molecular ions, the main of which is the elimination of an N,N'-dimethylcarbodiimide molecule.
  PubDate: 2023-05-01
A Novel Reaction of Sulfonyl Azides with Phosphine Sulfides
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  Abstract: (4-Methoxyphenyl)di(pyrrolidin-1-yl)phosphine sulfides were synthesized by the reaction of Lausson’s reagent with cyclic amines. It was shown for the first time that phosphine sulfides react with arenesulfonyl azides in 1,4-dioxane under reflux with the elimination of nitrogen and elemental sulfur to form previously unknown dicycloaminophosphoranylidene sulfonamides.
  PubDate: 2023-05-01
Diastereoselective Synthesis of
3-[2-Chloro(bromo)phenyl]-2-methyl-2-[(prop-2-yn-1-yl)oxy]oxiranes and
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  Abstract: The reaction of halogen-substituted benzaldehydes with 3-(1-chloroethoxy)prop-1-yne leads to the formation of unsaturated ethers derived from 2-hydroxyoxirane. The formation of the latter was confirmed by its reaction with acetone in the presence of BF3·Et2O to give substituted 1,3-dioxolanes.
  PubDate: 2023-05-01