Russian Journal of Organic Chemistry
Russian Journal of Organic Chemistry is a peer-reviewed journal that covers all aspects of modern organic chemistry, including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis. Previously focused on translation, the journal now has the aim to become an international publication and accepts manuscripts originally submitted in English from all countries, along with translated works.
Peer review and editorial policy
The journal follows the Springer Nature Peer Review Policy, Process and Guidance, Springer Nature Journal Editors' Code of Conduct, and COPE's Ethical Guidelines for Peer-reviewers.
Approximately 15% of the manuscripts are rejected without review based on formal criteria as they do not comply with the submission guidelines. Each manuscript is assigned to two peer reviewers. The journal follows a double-blind reviewing procedure. The period from submission to the first decision is up to 7 days. The approximate rejection rate is 63%. The final decision on the acceptance of a manuscript for publication is made by the Editor-in-Chief.
If Editors, including the Editor-in-Chief, publish in the journal, they do not participate in the decision-making process for manuscripts where they are listed as co-authors.
Special issues published in the journal follow the same procedures as all other issues. If not stated otherwise, special issues are prepared by the members of the editorial board without guest editors.
Current Issue
Vol 55, No 12 (2019)
- Year: 2019
- Articles: 32
- URL: https://journals.rcsi.science/1070-4280/issue/view/13683
Article
Cu-MOF-Catalyzed Carboxylation of Alkynes and Epoxides
Abstract
The catalytic activity of copper-containing heterogeneous catalysts, in particular metal-organic frameworks, zeolites, and alumina-supported nanoparticles, in the carboxylation of terminal alkynes and oxiranes has been evaluated. Temperature dependences of these reactions have been studied.
Synthesis of Spiro[benzo[h]chromene-4,3′-indoles] and Spiro[benzo[f]chromene-1,3′-indoles]
Abstract
New spiro heterocycles, spiro[benzo[h]chromene-4,3′-indoles] and spiro[benzo[f]chromene-1,3′-indoles], have been synthesized in 50–60% yield by three-component condensation of substituted isatins with malononitrile or ethyl cyanoacetate and naphthalen-1-ol or naphthalen-2-ol. The described reactions follow a cascade cyclization pathway and provide a regioselective method of synthesis of the title compounds.
Synthesis of New Guanidine-Containing Amphiphiles and Their Pyrene Analog for Liposomal Delivery Systems and Visualization in Target Cells
Abstract
New cationic amphiphiles with a guanidine head group have been synthesized starting from lipoamino acids with the goal of creating drug and genetic material delivery systems. Their analog containing a pyrene fragment has also been obtained as a potential agent for visualization of liposome transport in various cells.
Synthesis of Nonano-9-lactone Fused to a δ-Lactone Ring
Abstract
With the goal of obtaining fused dilactones, the carbohydrate moiety of diastereoisomeric Michael adducts of levoglucosenone and cyclohexanone was converted to δ-lactone and its derivatives fused to an octahydrochromene fragment. The subsequent oxidative cleavage of the C-C bridge in the latter by the action of pyridiniun chlorochromate (PCC) afforded nonano-9-lactone fused at the C6-C7 bond to δ-lactone or methyl-δ-lactol. The presence of a carbonyl group in the carbohydrate moiety was found to prevent C-C bond cleavage.
Synthesis and Azido-Tetrazole Tautomerism of New Methylsulfanyl Thieno[3,2-d]pyrimidine Derivatives
Abstract
New 7-amino, 7-azido, and 7-alkylsulfanyl derivatives have been synthesized from 7-chloro-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1H-cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine. 7-Azido-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1H-cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]-pyrimidine has been found to exist in solution as a mixture of azido and tetrazole tautomers, whereas only its tetrazole form is present in the crystalline state.
Synthesis of New (Arylsulfanyl)maleimide Derivatives
Abstract
Previously unknown 2-(arylsulfanyl)-3-hydroxymaleimide and 2-(arylsulfanyl)-3-chloromaleimide derivatives have been synthesized, and several synthetic approaches to 2-(arylamino)-3-(arylsulfanyl)-maleimides have been tested. The reactivities of 2-chloro-3-(4-methylphenylsulfanyl)maleimide and 2,3-bis(4-methylphenylsulfanyl)maleimide toward nitrogen and sulfur nucleophiles have been studied, and products of substitution of one or two arylsulfanyl groups have been obtained.
Mass Spectra of New Heterocycles: XX. Electron Impact and Chemical Ionization Mass Spectra of 5-(Prop-2-yn-1-ylsulfanyl)-1H-pyrrol-2-amines
Abstract
Electron impact (70 eV) and chemical ionization (methane as reactant gas) mass spectra of 1-alkyl- and 1-[2-(vinyloxy)ethyl]-5-(prop-2-yn-1-ylsulfanyl)-1H-pyrrol-2-amines have been studied for the first time. The title compounds under electron impact form stable molecular ions which decompose mainly along pathways typical of the molecular ions derived from the corresponding intramolecular cyclization products, 7-alkyl- and 7-[2-(vinyloxy)ethyl]-2,7-dihydrothiopyrano[2,3-b]pyrrol-6-amines. In addition, fragment ions that could be formed only via decomposition of unrearranged molecular ion were detected. The main fragmentation pathway of their molecular ions involves cleavage of the N1-CAlk bond with the formation of stable [M − R3]+ ions (Irel 85–100%) {except for N,N-diethyl- and N,N-dipropyl-1-[2-(vinyloxy)emyl]-5-(prop-2-yn-1-ylsulfanyl)-1H-pyrrol-2-amines}. The results of quantum chemical calculations at the B3LYP/6-311+G(d,p) level of theory are consistent with the experimental data. In the chemical ionization mass spectra of 5-(prop-2-yn-1-ylsulfanyl)-1H-pyrrol-2-amines, the major peaks were those corresponding to M+· (Irel 65–100%) and [M + H]+ (Irel 75–100%). The title compounds have been found to undergo partial (5–10%) thermally induced isomerization to 5-(prop-1-yn-1-ylsulfanyl)-1H-pyrrol-2-amines under the chemical ionization conditions.
New Reaction of Dimethylformamide with Acrylic Acid
Abstract
A new homogeneous reaction of dimethylformamide (DMF) with acrylic acid was studied. The reaction afforded previously unknown 3-[2-carboxyethyl(dimethyl)azaniumyl]propanoate and carbon monoxide. The product structure was determined by 1H and 13C NMR spectroscopy, X-ray diffraction, and elemental analysis, and evolution of gaseous carbon monoxide was confirmed by GC/MS. The kinetic parameters of the described reaction and its overall order were determined.
New Differently Functionalized Cyclopentenediones
Abstract
2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione reacted with highly nucleophilic secondary (diethylamine, morpholine, N-methylpiperazine, piperidine) and primary amines (allylamine) under mild conditions (methanol, 20°C, 24 h) to give products of substitution of the 4-chlorine atom in 60–87% yield. The reaction of the same compound with a weak nitrogen nucleophile, imidazole, afforded 4-(1H-imidazol-1-yl) derivative in a low yield (25%). Methionine methyl ester hydrochloride failed to react with 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione in methanolic potassium hydroxide; instead, 55% of 2-allyl-2-chloro-4-methoxy-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione was obtained. The reaction with methyl 2-sulfanylacetate in the presence of sodium hydride produced methyl {[4-allyl-4-chloro-3,5-dioxo-2-(2,4,6-trimethoxyphenyl)cyclopent-1-en-1-yl]sulfanyl}acetate in 47% yield.
Oxidation of Thioamides to Amides with Tetrachloro- and Tetrabromoglycolurils
Abstract
Tetrabromo- and tetrachloroglycolurils have been shown to act as good oxidants capable of converting thioamides to the corresponding amides. This approach offers such advantages as good yields (81–99%), short reaction times (10–25 min), simple workup procedure, and environmental safety.
Synthesis and Spectral and Coordination Properties of meso-Tetraarylporphyrins
Abstract
5,10,15,20-Tetrakis(3,5-dibromophenyl)porphyrin and 5,10,15,20-tetrakis(3-bromo-4-methoxy-phenyl)porphyrin have been synthesized, and their complexing properties with respect to Pd2+ ion in acetonitrile at 308–328 K have been studied by spectrophotometry. The synthesized compounds were characterized by UV-Vis, 1H NMR, and mass spectra. The effect of substitueras in the meso-phenyl rings of the ligands on their spectral and coordination properties was estimated in comparison to 5,10,15,20-tetraphenylporphyrin.
Synthesis of New Derivatives of 5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione
Abstract
5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione reacted with cyclohexyl and benzyl (4-aminophenyl)carbamates in boiling ethanol in the presence of a catalytic amount of glacial acetic acid to give the corresponding Schiff bases, cyclohexyl and benzyl (4-{[(E)-1-(4-hydroxy-2,6-dioxo-3,6-dihydro-2H-1,3-thiazin-5-yl)ethylidene]amino}phenyl)carbamates. Heating of the latter in dimethylformamide for 2 h was accompanied by evolution of COS with the formation of cyclohexyl and benzyl {4-[6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]phenyl}carbamates. The condensation of the title compound with benzene-1,2-diamine in propan-2-ol, followed by addition of 5-arylfuran-2-carbaldehyde and trifluoroacetic acid afforded 5-(2-{5-[4-bromo(nitro)phenyl]furan-2-yl}-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-4-hydroxy-2H-1,3-thiazine-2,6(3H)-diones. 5-((E)-3-{5-[4-Bromo(nitro)phenyl]furan-2-yl}prop-2-enoyl)-4-hydroxy-2H-1,3-thiazine-2,6(3H)-diones were synthesized by condensation of 5-acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione with 5-[4-bromo(nitro)phenyl]furan-2-carbaldehydes in chloroform in the presence of catalytic amounts of pyridine and piperidine.
One-Pot Syntheses with 2-Substituted 6-Aminopyrimidin-4(3H)-ones: New 5-Aryl-5,8,9,10-tetrahydropyrimido[4,5-b]-quinoline-4,6(3H,7H)-diones and 5,5′-(Arylmethylene)-bis[6-amino-2-methylpyrimidin-4(3H)-ones]
Abstract
One-pot condensation of 2-substituted 6-aminopyrimidin-4(3H)-ones with aromatic aldehydes and 5,5-dimethylcyclohexane-1,3-dione (dimedone) in acetic acid without a catalyst afforded new substituted 5-aryl-5,8,9,10-tetrahydropyrimido[4,5-b]quinoline-4,6(3H,7H)-diones in good yields. The condensation of 2-memyl-6-aminopyrirnidin-4(3H)-one with aromatic aldehydes at a molar ratio of 2:1 under similar conditions led to the exclusive formation of uncyclized 5,5′-(arylmemylene)bis[6-amino-2-methylpyrimidin-4(3H)-ones].
New 4-Substituted 5-(1H-Pyrrol-2-ylmethyl)-4H-thieno[3,2-b]pyrroles and Their Reactions with N-Bromosuccinimide
Abstract
5-(1H-Pyrrol-2-ylmethyl)-4H-thieno[3,2-b]pyrroles were synthesized by condensation of N-substituted (4H-thieno[3,2-b]pyrrol-5-yl)methanols with pyrrole in the presence of Amberlyst 15 as catalyst. Treatment of the products with N-bromosuccinimide led to the formation of dark blue polymers insoluble in organic solvents.
Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones
Abstract
A green approach was proposed for the synthesis of 2-chloroprop-2-en-1-yl sulfones in 47–94% yield. The molecular and crystal structures of 2-chloroprop-2-en-1-yl phenyl sulfone and 2-chloroprop-2-en-1-yl methyl sulfone were determined by X-ray analysis. π-Stacking interaction between the benzene ring and double bond was revealed in the crystal structure of 2-chloroprop-2-en-1-yl phenyl sulfone. Chloropropenyl sulfones were found to readily undergo dehydrochlorination to give stable allenyl sulfones and alkaline hydrolysis to produce the corresponding acetonyl sulfones. The latter can be converted to oximes by treatment with hydroxylamine hydrochloride.
Synthesis of Potentially Biologically Active Fused Polyheterocycles Containing a Pyrimidine Unit
Abstract
A number of new fused polyheterocyclic compounds were synthesized on the basis of 2-amino-6-sulfanylpyrirnidin-4(3H)-one. In particular, reactions of 2-amino-6-suffanylpyrirnidin-4(3H)-one with cinnamic acids, aroyl isothiocyanate, and acetic anhydride afforded imidazo[1,2-a]thieno[2,3-d]pyrimidine, [1,3]thiazino[6′,5′: 4,5]pyrimido[1,2-a][1,3,5]triazine, and imidazo[1,2-a]tWeno[2,3-d]pyrimidine derivatives, respectively. The alkylation of 2-amino-6-smfanylpyrirnidin-4(3H)-one with benzyl chloride gave 3-benzyl-6-(benzylsulfanyl)-2-imino-2,5-dihydropyrimidin-4(3H)-one which was converted to [1,3]thiazolo[5,4-d][1,2,4]triazolo-[4,3-a]pyrimidine, imidazo[1,2-a]pyrimidine, dihydropyrimido[4,5-b]quinoline, imidazo[1,2-a]pyrrolo[2,3-d]-pyrimidine, and benzo[g]imidazo[2,1-b]pteridine derivatives via reactions with nitrous acid, ethyl chloroacetate, and aniline (followed by treatment with carbon disulfide, cinnamic acid, or sodium nitrite in acetic acid). 2-Amino-3,4-dihydropyrimidin-6-sulfonic acid was obtained by oxidation of the same substrate with hydrogen peroxide in alkaline medium. Some of the synthesized compounds showed antimicrobial activity.
A New Facile Ultrasound-Assisted Magnetic Nano-[CoFe2O4]-Catalyzed One-Pot Synthesis of Pyrano[2,3-c]pyrazoles
Abstract
Pyrano[2,3-c]pyrazole derivatives have been synthesized through a one-pot multicomponent condensation of various aldehydes, dialdehydes, and ketones with malononitrile, ethyl acetoacetate, hydrazine hydrate (or phenylhydrazine) in the presence of magnetic nano-[CoFe2O4] catalyst under ultrasonic irradiation. The catalyst can be recovered using an external magnet and used repeatedly.
5-Methyl-4-[3-(2-oxopyrrolidin-1-yl)propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one: Synthesis, Characterization, and DFT Study
Abstract
5-Methyl-4-(3-(2-oxopyrrolidin-1-yl)propyl)-2,4-dihydro-3H-1,2,4-triazol-3-one was synthesized and characterized by X-ray, FTIR and NMR spectroscopic techniques. The molecular geometry and spectral parameters of the title compound were also computed by the DFT/B3LYP76-311++G(d,p) method, and the theoretical data showed a good agreement with the experimental ones. The differences between the theoretical and experimental IR and NMR spectra supported the presence of inter- and intramolecular C-H⋯O and intermolecular N-H⋯O hydrogen bonds, which were revealed by X-ray analysis. Nonlinear optical (NLO) properties of the title compound were analyzed by the DFT/B3LYP/6-311++G(d,p) method by calculating the mean polarizability (α) and first-order hyperpolarizability values (β) (α = 22.0746454×10−24, β = 10.1110649×10−31 esu). As compared with the corresponding data for urea (α = 4.9067×10−24, β = 7.8782×10−31 esu), these values suggest promising NLO properties.
Self-Catalyzed One-Pot Four-Component Green Synthesis of 2-Amino-6-[1,4-dioxo-3,4-dihydrophthalazin-2(1H)-yl]-4-phenyl-4H-pyran-3,5-dicarbonitriles
Abstract
The title compounds were synthesized in good yields by one-pot four-component condensation of phthaloyl dichloride, ethyl cyanoacetohydrazide, malononitrile, and substituted benzaldehydes in boiling ethanol for 1–2 h. The reaction involves in situ generation of hydrogen chloride in the first step, which catalyzes further addition, dehydration, and cyclization steps. The procedure is advantageous due to easy workup, short reaction times, good yields, the use of ethanol as a green solvent, and no external catalyst is needed.
2-Cyano-N′-[(1,3-diphenyl-1H-pyrazol-4-yl)methylidene]acetohydrazide in the Synthesis of Nitrogen Heterocycles
Abstract
Some interesting nitrogen heterocycles, as well as other products, were synthesized by reactions of 2-cyano-N′-[(1,3-diphenyl-1H-pyrazol-4-yl)methylidene]acetohydrazide with phenyl isothiocyanate/elemental sulfur, 3,4,5-trimethoxybenzaldehyde, 4-hydroxy-1,1′-biphenyl-3-carbaldehyde, 2-oxoquinoline-3-caraldehyde, triethyl orthoformate, ethyl cyanoacetate, and thiosemicarbazide. The structures of all isolated compounds were established from their analytical and spectral data.
A Recyclable Heterogeneous Palladium Catalyst Anchored to Modified Metal-Organic Framework for Hydrogenation of Styrene Oxide
Abstract
A heterogeneous palladium(II) catalyst anchored to modified metal-organic framework has been synthesized and characterized. The performance of the catalyst has been tested for the hydrogenation of styrene oxide at ambient temperature and pressure. The catalyst showed an excellent activity and selectivity for the preparation of 2-phenylethanol from styrene oxide with 100% conversion and 98% selectivity. The catalyst is very stable and easily recyclable for several times without loss of activity.
Synthesis and Enzyme Inhibitory Activity of Novel Pyridine-2,6-dicarboxamides Bearing Primary Sulfonamide Groups
Abstract
New pyridine-2,6-dicarboxamide derivatives containing sulfonamide groups were synthesized by the coupling of pyridine-2,6-dicarbonyl dichloride and various aminobenzenesulfonamides in a mixture of dichloromethane and acetone. The pyridinedicarboxamide-based sulfonamides were evaluated as carbonic anhydrase (CA) and cholinesterase (ChE) inhibitors, and they showed IC50 values in the ranges 12.8–37.6 nM against human carbonic anhydrase I (hCA I), 17.8–46.7 nM against human carbonic anhydrase II (hCA II), 98.4–197.5 nM against acetylcholinesterase (AChE), and 82.2–172.7 nM against butyrylcholinesterase (BuChE). These results are comparable with those for known inhibitors such as acetazolamide (IC50 = 32.1 nM for hCA I and IC50 = 51.0 nM for hCA II) and rivastigmine (IC50 = 60.2 nM for AChE and IC50 = 14.0 nM for BuChE), which qualifies the synthesized compounds as candidates for a more in-depth study.
Green Nano-Silica Sulfuric Acid-Catalyzed Synthesis of New 6-Amino-8-aryl-7-(benzenesulfonyl)-2-(hydroxymethyl)-pyrano[3,2-b]pyran-4(8H)-one Derivatives
Abstract
Some new 6-amino-8-aryl-7-(benzenesulfonyl)-2-(hydroxymethyl)pyrano[3,2-b]pyran-4(8H)-ones have been synthesized in improved yields by one-pot three-component reaction of aromatic aldehydes with benzenesulfonylacetonitrile and 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one in the presence of nano-silica sulfuric acid. The catalyst can be recovered by simple filtration and reused further.
Synthesis and Antimicrobial Screening of Novel Azetidin-2-ones Derived from Pyromellitic Diimide via [2+2]-Cycloaddition Reaction
Abstract
A series of novel 2-azetidinone derivatives have been obtained starting from pyromellitic dianhydride. Pyromellitic dianhydride was converted to pyromellitic diimide using sodium cyanate, and the diimide was alkylated with ethyl chloroacetate. The resulting diester was treated with hydrazine hydrate to obtain dihydrazide which reacted with substituted pyridine-2-carbaldehydes to give the corresponding Schiff bases, and [2+2]-cycloaddition of the latter with chloroacetyl chloride in the presence of triethylamine afforded the target azetidin-2-one derivatives. The newly synthesized compounds showed high antimicrobial activities against some bacterial and fungal strains.
Short Communications
Synthesis of Functionalized Bicyclic Compounds Based on 2-(1-Arylethylidene)malononitriles
Abstract
New tetrahydroisoquinoline-5,7-dicarbonitrile derivatives have been synthesized by piperazine hydrate-catalyzed reaction of acetoacetanilide with 2-(1-arylethylidene)malononitriles (Knoevenagel condensation products of acetophenones and malononitrile) in aqueous ethanol at room temperature. The product structure was confirmed by NMR spectra and X-ray analysis of 1,6-diamino-4a-methyl-3-oxo-2,8-diphenyl-2,3,4,4a-tetrahydroisoquinoline-5,7-dicarbonitrile.
Chemoselective Vinylation of the Quinine Hydroxy Group with the System Electron-Deficient Acetylene/Diphenylphosphine Oxide: an Alternative to SNHAr Reaction
Abstract
Three-component SNHAr reaction of quinine, diphenylphosphine oxide, and furoylacetylene chemoselectively afforded the corresponding quinine vinyl ether and 2: 1 adduct of diphenylphosphine oxide to the triple bond of furoylacetylene instead of the expected cross-coupling product at the pyridine ring.
Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
Abstract
(S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol was synthesized in two steps by the Diels-Alder reaction of penta-2,4-dien-1-ol with diethyl azodicarboxylate in the presence of (S)-BINOL as chiral catalyst. The subsequent Boc-protection of the 2-position of the pyridazine ring, ring-closing carbonylation of the hydroxy group, and deprotection afforded a bicyclic iminosugar analog. The structure of the isolated compounds was proved by NMR, IR, and mass spectra and elemental analyses.
Reaction of Disodium Ethene-1,1-bis(thiolates) with 1,1,2-Trichloroethane
Abstract
Previously unknown chloro-substituted 1,3-dithiolanes were synthesized by reaction of disodium 2-cyanoethene-1,1-bis(dithiolates) with 1,1,2-trichloroethane. The reaction of disodium 2-cyano-3-ethoxycarbonylprop-1-ene-1,1-bis(dithiolate) afforded ethyl 2-cyano-2-(2H-1,3-dithiol-2-ylidene)acetate.
Modification of Monocarboxylic Acid Hydrazides with Tropylium Salts
Abstract
Nicotinic, isonicotinic, and furan-2-carboxylic acid hydrazides reacted with 2 equiv of tropylium perchlorate or tetrafluoroborate to give the corresponding N′N′-di(cyclohepta-2,4,6-trein-1-yl) derivatives as a result of electrophilic substitution of both hydrogen atoms in the primary amino group. The reaction of furan-2-carbohydrazide with an equimolar amount of tropylium salt gave N′-(cyclohepta-2,4,6-trien-1-yl)furan-2-carbohydrazide.
Reaction of Thioxanthylium Cation with Pharmacophoric Heterocyclic Amines
Abstract
Reactions of thioxanthylium tetrafluoroborate with pharmacophoric heterocyclic amines, pyrimidin-2-amine, 4,6-dimethylpyrimidin-2-amine, 2-aminopyrimidine-4,6-diol, and 1,3,4-thiadiazole-2,5-diamine, gave stable products of electrophilic substitution of one hydrogen atom per amino group. The product structure was confirmed by 1H NMR and mass spectra and X-ray analysis of N-(9H-tmoxanthen-9-yl)pyrimidin-2-amine.