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卷 55, 编号 10 (2019)

Review

Copper in Cross-Coupling Reactions: I. Sonogashira-Hagihara Reaction

Murashkina A., Mitrofanov A., Beletskaya I.

摘要

The review addresses the problem of using copper catalysts in the palladium-free version of the Sonogashira-Hagihara reaction. Particular attention is paid to ligand-free catalytic systems, the use of water as solvent, and recyclability of catalysts.

Russian Journal of Organic Chemistry. 2019;55(10):1445-1458
pages 1445-1458 views

Article

Ring Opening of 4-Arylamino-2-tert-butyl-5-oxo-2,5-dihydrofuran-2-yl Acetates with Aromatic and Heterocyclic Amines

Igidov N., Rubtsov A.

摘要

Reactions of 4-arylamino-2-tert-butyl-5-oxo-2,5-dihydrofuran-2-yl acetates with an equimolar amount of aromatic or heterocyclic amine in toluene involves initial attack of the amine on the C2 atom of the furan ring, followed by opening of the furan ring and elimination of acetic acid to give N-aryl(hetaryl)-2-arylamino-5,5-dimethyl-4-oxohex-2-enamides.

Russian Journal of Organic Chemistry. 2019;55(10):1459-1464
pages 1459-1464 views

New 11,13-Dienone Analog of Cloprostenol

Vostrikov N., Zagitov V., Miftakhov M.

摘要

Cloprostenol methyl ester was converted to the corresponding Δ11,13-15-keto analog through 9,11-dihydroxy-15-oxo derivative which was subjected to exhaustive acylation and DBU-promoted removal of the 11-acetoxy group. The key stages of the transformation included protection of the 9,11-dihydroxy functionality of cloprostenol methyl ester via conversion to cyclic phenylboronate, in situ oxidation of the unprotected 15-hydroxy group of the latter, and exhaustive acetylation to obtain the corresponding diacetate as precursor to the target compound. An alternative synthetic path starting from 9α,11α-O-bis[tert-butyl(di-phenyl)silyl]-15-oxo derivative of cloprostenol methyl ester has also been proposed.

Russian Journal of Organic Chemistry. 2019;55(10):1465-1468
pages 1465-1468 views

Synthesis and Oxidation of Myrtanethiol and Its Functional Derivatives with Chlorine Dioxide

Grebyonkina O., Lezina O., Izmest’ev E., Frolova L., Rubtsova S., Kutchin A.

摘要

cis-Myrtanethiol and a mixture of diastereoisomeric myrtanethiols were synthesized starting from (-)-β-pinene. Their oxidation with chlorine dioxide afforded a number of derivatives such as disulfides, S-thiol-sulfonates, sulfonyl chlorides, and sulfonic acids. The effects of reaction conditions (solvent nature, reactant molar ratio, reaction time, catalyst) on the yield and ratio of the products were studied. The corresponding sulfonyl chloride was obtained in quantitative yield by oxidation of thiol in the presence of vanadyl acetyl-acetonate, and optimal conditions were found for quantitative formation of myrtanesulfonic acid.

Russian Journal of Organic Chemistry. 2019;55(10):1469-1475
pages 1469-1475 views

Azo Coupling of Enamino Amides of the 3,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline Series with Arenediazonium Salts

Mikhailovskii A., Pogorelova E., Pershina N., Lyust E., Dmitriev M.

摘要

The azo coupling of arenediazonium chlorides with (Z)-2-(3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene)-N-(4-methylphenyl)acetamide afforded (Z)-2-(2-arylhydrazinylidene)-2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-N-(4-methylphenyl)acetamides whose structure was confirmed by 1H NMR and X-ray diffraction data. The azo coupling products containing no p-tolyl substituent on the amide nitrogen atom exist in solution as mixtures of azo and hydrazone tautomers. Electronic absorption spectra of the synthesized compounds were studied.

Russian Journal of Organic Chemistry. 2019;55(10):1476-1482
pages 1476-1482 views

Functional Derivatives of 4-Formyl-2-methoxyphenyl Pyridine-4-carboxylate

Potkin V., Bumagin N., Dikusar E., Petkevich S., Kurman P.

摘要

Acylation of vanillin with isonicotinoyl chloride gave 4-formyl-2-methoxyphenyl pyridine-4-carboxylate which was converted into a number of functional derivatives, including those containing isoxazole and isothiazole heterocycles. In particular, the condensation of the title compound with primary amines afforded the corresponding Schiff bases. 4-Formyl-2-methoxyphenyl pyridine-4-carboxylate and one of the Schiff bases derived therefrom were reduced with sodium triacetoxohydridoborate to the corresponding alcohol and amine which were acylated with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides to obtain esters and amides having isoxazole and isothiazole fragments. The synthesized compounds readily formed complexes with palladium(II) chloride, which showed a high catalytic activity in the Suzuki reaction of 3-bromobenzoic acid with 4-methoxyphenylboronic acid in water in the absence of an organic solvent.

Russian Journal of Organic Chemistry. 2019;55(10):1483-1494
pages 1483-1494 views

Halogenation and μH Tautomerism of 7-Benzyl-7,8-dicarba-nido-undecaborate(−1) Anion

Rudakov D., Genaev A., Dikusar E., Zvereva T., Zubreichuk Z., Potkin V.

摘要

Deboration of 1-PhCH2-1,2-C2B10H11 by heating in ethanolic potassium hydroxide afforded Me4N+ [7-PhCH2-7,8-C2B9H11] which was treated with excess halosuccinimide (NCS, NBS) in acetonitrile or with elemental iodine or bromine in methanol to obtain Me4N+ [7-PhCH2-9,11-X2-7,8-C2B9H9] (X = Cl, Br, I). The reaction of 1-PhCH2-1,2-C2B10H11 with an equimolar amount of iodine gave a mixture of Me4N+·[7-PhCH2-11-I-7,8-C2B9H10]- and Me4N+[7-C6H5CH2-9-I-7,8-C2B9H10] at a ratio 1:1.8 due to steric effect of the benzyl substituent. The 11B chemical shifts of each μ-H tautomer of Me4N+ [7-PhCH2-9,11-X2-7,8-C2B9H9] (X = H, F, Cl, Br, I) were calculated at the DFT level of theory, and their contributions to the average 11B NMR spectrum and the corresponding tautomeric equilibrium constants were determined.

Russian Journal of Organic Chemistry. 2019;55(10):1495-1503
pages 1495-1503 views

Formyl Derivatives of Amino-Substituted Polyfluorotriphenyl-4,5-dihydro-1H-pyrazoles: Synthesis and Use as Donor Blocks of Nonlinear Optical Chromophores

Shelkovnikov V., Orlova N., Kargapolova I., Erin K., Maksimov A., Chernonosov A.

摘要

A series of new formyl derivatives of polyfluorinated triphenyl-4,5-dihydro-1H-pyrazoles containing various amine residues in the fluorinated benzene ring have been synthesized and used as donor building blocks in the synthesis of donor–acceptor dyes as potential chromophores for nonlinear electro-optics. Effects of substituents in the donor and acceptor moieties of the obtained chromophores on their spectral characteristics have been studied.

Russian Journal of Organic Chemistry. 2019;55(10):1504-1517
pages 1504-1517 views

Plant Coumarins: XVII. Synthesis and Transformations of 7-Hydroxy-2-oxo-2H-chromene-6-carboxamides

Zakharov D., Lipeeva A., Gatilov Y., Makarov A., Shults E.

摘要

Umbelliferone-6-carbonyl chloride reacted with amines and α-, β-, and ω-amino acid methyl esters to afford the corresponding N-substituted 7-hydroxy-2-oxo-2H-chromene-6-carboxamides. The reaction of umbelliferone-6-carbonyl chloride with glycine gave 2-(7-hydroxy-2-oxo-2H-chromene-6-carboxamido)acetic acid which was converted into acid chloride, and the latter reacted with benzylamines and α-amino acid methyl esters to produce compounds containing a dipeptide fragment.

Russian Journal of Organic Chemistry. 2019;55(10):1518-1526
pages 1518-1526 views

Reaction of Lithium Acylate α-Carbanions with Carbon Tetrabromide

Zorin A., Zaynashev A., Zorin V.

摘要

Lithium acylate α-carbanions generated by metalation of acetic, butanoic, and 2-methylpropanoic acids with lithium diisopropylamide in THF under argon reacted with carbon tetrabromide at 20-25°C (2 h) to produce butanedioic acid or its 2,3-diethyl and 2,2,3,3-tetramethyl derivatives, as well as the corresponding 2-bromocarboxylic acids and bromoform. The effect of the halogen nature in carbon tetrahalide (CCl4, CBr4) on the reaction selectivity is discussed.

Russian Journal of Organic Chemistry. 2019;55(10):1527-1531
pages 1527-1531 views

Synthesis and Quantification of 2-(Diethylamino)-N-(2-methylphenyl)acetamide Nitrate

Chekryshkina L., Demin A., Tumashov A., Babikova E., Slepova N.

摘要

A procedure for the synthesis of 2-(diethylamino)-N-(2-methylphenyl)acetamide nitrate (monomecaine) exhibiting a pronounced antiarrhythmic activity has been optimized. A procedure for its identification and quality control of the drug substance by HPLC has been developed, and the limit of detection of o-toluidine impurity therein has been estimated at 0.02%. Procedures for HLPC and extraction-titration quantification of monomekain in the drug substance have been proposed and validated. The obtained relative standard deviation (RSD) indicates good specificity, linearity, and precision of the developed procedures.

Russian Journal of Organic Chemistry. 2019;55(10):1532-1538
pages 1532-1538 views

Synthesis of Nitro, Amino, and Halo Derivatives of 2-Ethyl-2-methyl-2,3-dihydro-1H-indole

Salikhov S., Latypova L., Mustafin A., Ayupov D., Vasilova L., Zorin V., Abdrakhmanov I.

摘要

The nitration, oxidative halogenation, and radical bromination and chlorination of 2-ethyl-2-methyl-2,3-dihydro-1H-indole afforded the corresponding nitro, amino, and halo derivatives. The synthesized compounds were evaluated for their antioxidant, antimicrobial, and plant growth regulating activities.

Russian Journal of Organic Chemistry. 2019;55(10):1539-1546
pages 1539-1546 views

Synthesis of 9-Substituted Imidazo[1,2-a]benzimidazoles Containing a 5-Nitrofuran-2-yl Fragment

Kuzmenko T., Divaeva L., Sayapin Y., Morkovnik A., Borodkin G.

摘要

9-Substituted 2-(5-nitrofuran-2-yl)-9H-imidazo[1,2-a]benzimidazoles were synthesized for the first time by cyclization of quaternary salts obtained from 1-substituted benzimidazol-2-amines and 2-bromo-1-(5-nitrofuran-2-yl)ethan-1-one. 9-R-2-Methyl(aryl)-9H-imidazo[1,2-a]benzimidazoles reacted with 5-nitrofuran-2-carbaldehyde and 4-nitrobenzaldehyde to give the corresponding secondary alcohols as a result of aldehyde addition to the 3-position of the tricyclic system. The Witting olefination of ethyl 2-(bromomethyl)-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate afforded 2-ethenylimidazo[1,2-a]benzimidazoles.

Russian Journal of Organic Chemistry. 2019;55(10):1547-1553
pages 1547-1553 views

Synthesis and Acid–Base Properties of β-Octabromo-Substituted Unsymmetrical Nitrophenylporphyrins

Ivanova Y., Chizhova N., Mamardashvili N.

摘要

The bromination of [5-(4-nitrophenyl)-10,15,20-triphenylporphyrinato]cobalt(II) and [5,10,15-tris-(4-nitrophenyl)-20-phenylporphyrinato]cobalt(II) with N-bromosuccinimide in a mixture of chloroform and dimethylformamide gave [2,3,7,8,12,13,17,18-octabromo-5-(4-nitrophenyl)-10,15,20-triphenylporphyrinato]-cobalt(II) and [2,3,7,8,12,13,17,18-octabromo-5,10,15-tris(4-nitrophenyl)-20-phenylporphyrinato]cobalt(II). Treatment of the cobalt complexes with a mixture of perchloric and sulfuric acids afforded the corresponding metal-free porphyrins. Electron absorption, 1H NMR, and mass spectra of the synthesized compounds were studied, and acidity and basicity constants of the porphyrin ligands in acetonitrile were determined.

Russian Journal of Organic Chemistry. 2019;55(10):1554-1561
pages 1554-1561 views

Heck Synthesis of New Organosilicon Oligo(arylenevinylenes)

Pyatakov D., Borshchev O., Skorotetcky M., Ponomarenko S.

摘要

Two alternative synthetic approaches to new silicon-containing oligo(arylenevinylenes), 1,4-bis-{(E)-2-[4-(trimethylsilyl)phenyl]ethenyl}benzene and 9,10-bis{(E)-2-[4-(trimethylsilyl)phenyl]ethenyl}anthracene via Heck reactions of trimethyl(4-vinylphenyl)silane with the corresponding dibromoarenes and of (4-bromophenyl)trimethylsilane with the corresponding divinylarenes were studied. The reaction of 9,10-divinylanthracene with (4-bromophenyl)trimethylsilane was found to be accompanied by elimination of one trimethylsilyl group.

Russian Journal of Organic Chemistry. 2019;55(10):1562-1568
pages 1562-1568 views

Synthesis and Characterization of Compounds Potentially Related to the Janus Kinase Inhibitor Baricitinib

Dasari S., Seelam N., Jayachandra S., Vadali L., Yerva E., Tondepu S., Gadakar M.

摘要

Nine compounds potentially related to the Janus kinase inhibitor Baricitinib have been identified, synthesized by conventional methods, and characterized by IR, 1H and 13C NMR, and mass spectral data.

Russian Journal of Organic Chemistry. 2019;55(10):1569-1574
pages 1569-1574 views

Green Regioselective Synthesis of (Purin-6-yl)hydrazones

Kapadiya K., Dhalani J., Patel B.

摘要

Some unique purine hydrazinylidene derivatives were synthesized by the regioselective reaction of 2,6-dichloropurine with hydrazine hydrate, followed by condensation with commercially available 1,3-dicarbonyl compounds according to a green chemistry approach. The structures of the synthesized compounds were confirmed by 1H and 13C NMR, IR, and mass spectra and elemental analyses. The regioselectivity of chlorine substitution in 2,6-dichloropurine was established by HMBC (Heteronuclear Multiple Bond Correlation) NMR technique.

Russian Journal of Organic Chemistry. 2019;55(10):1575-1579
pages 1575-1579 views

Convenient Synthesis of [1,2,4]Triazolo[4,3-a][1,3,5]triazin-5-amines, [1,2,4]Triazolo[4,3-c][1,3,5]thiadiazine-5-thiones, and [1,2,4]Triazolo[4,3-c][1,3,5]thiadiazin-5-imines from N-(4H-1,2,4-Triazol-3-yl) Carboximidates

Hajri A., Marzouki L.

摘要

The condensation of 4H-1,2,4-triazol-3-amine with ortho esters derived from acetic, propionic, and benzoic acids gave the corresponding N-(4H-1,2,4-triazol-3-yl) carboximidates which were treated with cyan-amide, carbon disulfide, and sodium thiocyanate to afford 7-substituted [1,2,4]triazolo[4,3-a][1,3,5]triazin-5-amines, [1,2,4]triazolo[4,3-c][1,3,5]thiadiazine-5-thiones, and [1,2,4]triazolo[4,3-c][1,3,5]thiadiazin-5-imines, respectively. The structures of the synthesized compounds were confirmed by IR, 1H and 13C NMR, and mass spectra and elemental analyses.

Russian Journal of Organic Chemistry. 2019;55(10):1580-1583
pages 1580-1583 views

Novel Fe3O4/SiO2/PPA Magnetic Nanoparticles: Preparation, Characterization, and First Catalytic Application to the Solvent- Free Synthesis of Tetrahydrobenzo[a]xanthene-11-ones

Amarloo F., Zhiani R., Mehrzad J.

摘要

Novel Fe3O4/SiO2/PPA nanoparticles were used as solid acid support in the solvent-free synthesis of 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones via multicomponent condensation of aromatic aldehydes with naphthalen-2-ol and 5,5-dimethylcyclohexane-1,3-dione. The target products were obtained in good to high yields. The Fe3O4/SiO2/PPA nanoparticles were thoroughly characterized by scanning electron microscopy, transmission electron microscopy, Fourier-transform IR spectroscopy, and energy-dispersive C-ray spectroscopy. The new catalyst has a high activity and is environmentally friendly, heterogeneous, easily recoverable, and recyclable without loss of catalytic activity.

Russian Journal of Organic Chemistry. 2019;55(10):1584-1590
pages 1584-1590 views

Synthesis of Tetrazoles from Amines Mediated by New Copper Nanocatalyst

Ariannezhad M., Habibi D., Heydari S.

摘要

New copper nanocatalyst was prepared by coating Fe3O4 magnetic nanoparticles with tetraethyl orthosilicate (TEOS), followed by functionalization with 3-chloropropyl(trimethoxy)silane and 4H-1,2,4-tri-azol-4-amine and complexation with copper(II) chloride. The new catalyst was characterized by various spectroscopic methods and was successfully used in the synthesis of 1-aryl-1H-tetrazoles by reaction of aromatic amines with sodium azide and triethyl orthoformate under solvent-free conditions at 100°C.

Russian Journal of Organic Chemistry. 2019;55(10):1591-1597
pages 1591-1597 views

Highly Diastereoselective Metal-Free Catalytic Synthesis of Drug-Like Spiroimidazolidinone

Jassem A., Raheemah A., Radhi W., Alid A., Jaber H.

摘要

A four-step procedure has been developed for the synthesis of (S)-3-isopropyl-1-[(R)-1-phenylethyl)- 1,4-diazaspiro[4.5]decan-2-one with high diastereoselectivity (up to 95% de) from (S)-α-aminoisovaleric acid (L-valine). Quantum chemical computations of the synthesized compound have been performed using Gaussian 09 software package.

Russian Journal of Organic Chemistry. 2019;55(10):1598-1603
pages 1598-1603 views

Efficient Synthetic Route to Access Linear and Angular Dibenzonaphthyridines

Sangeetha M., Manoj M.

摘要

An efficient procedure has been proposed for the synthesis of linear and angular phenyl-substituted dibenzonaphthyridines from anilinoquinolines and benzoic acid in up to 85% yield using Eaton’s reagent (a solution of phosphorous pentoxide in methanesulfonic acid) as condensing agent instead of polyphosphoric acid which previously afforded less than 50% yield of the same compounds. Apart from benzoic acid, ethyl benzoate and benzoyl chloride can be used in the synthesis of dibenzonaphthyridines according to the proposed procedure, but the yields are lower.

Russian Journal of Organic Chemistry. 2019;55(10):1604-1608
pages 1604-1608 views

Synthesis of Novel Triazolyl Thiourea Derivatives and Their Antibacterial Activity

Kazeminejad Z., Pourshamsian K., Hatamjafari F., Shiroudi A., Oliaey A.

摘要

4-Amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized in three steps from carbon disulfide, hydrazine hydrate, and acetic acid. Its reaction with benzoyl isothiocyanates prepared from substituted benzoyl chlorides and ammonium thiocyanate afforded the corresponding N-benzoyl-N′-triazolyl-thioureas. The obtained compounds were screened for antibacterial activity against Staphylococcus aureus (ATCC 25923), Staphylococcus epidermidis (ATCC 12228), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853). Their antibacterial activity against gram-positive bacteria was higher than against gram-negative bacteria, and derivatives containing electron-withdrawing groups were more active than those with electron-donating substituents.

Russian Journal of Organic Chemistry. 2019;55(10):1609-1615
pages 1609-1615 views

Short Communications

Synthesis of 6I-O-(4-Methylbenzenesulfonyl)-β-cyclodextrin

Novokshonov V., Xuan N., Shaglaeva N.

摘要

An improved procedure has been proposed for the synthesis of 6I-O-(4-methylbenzenesulfonyl)-β-cyclodextrin by reaction of β-cyclodextrin with p-toluenesulfonyl chloride in aqueous alkali. Repeated use of unreacted p-toluenesulfonyl chloride and reduction of the volume of water by half in combination with optimized conditions make it possible to obtain the target product in up to 58% yield without loss of purity.

Russian Journal of Organic Chemistry. 2019;55(10):1616-1617
pages 1616-1617 views

Reaction of Pyrrolo[2,1-a][1,4]oxazine-1,6,7-triones with Carbocyclic Enamino Ketones. Synthesis of Spiro[indole-3,2′-pyrroles]

Tretyakov N., Maslivets A.

摘要

8-Aroyl-3,4-dihydro-1H-pyrrolo[2,1-a][1,4]oxazine-1,6,7-triones reacted with 3-benzylamino-5,5-dimethylcyclohex-2-en-1-one to give 3′-aroyl-1-benzyl-4′-hydroxy-1′-(2-hydroxyethyl)-6,6-dimethyl-6,7-dihydrospiro[ indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-triones.

Russian Journal of Organic Chemistry. 2019;55(10):1618-1620
pages 1618-1620 views

Regioselective Reduction of the C3=C3a Double Bond in 3-Aroylpyrrolo[1,2-c][4,1]benzoxazepine-1,2,4-triones

Maslivets A., Maslivets A.

摘要

The reaction of 3-aroyl-1H,6H-pyrrolo[1,2-c][4,1]benzoxazepine-1,2,4-triones with thioglycolic acid resulted in regioselective reduction of the C3=C3a bond with the formation of 3-aroyl-2-hydroxy-1H,6H-pyrrolo[1,2-c][4,1]benzoxazepine-1,4(3aH)-diones.

Russian Journal of Organic Chemistry. 2019;55(10):1621-1622
pages 1621-1622 views

Synthesis and Solid State Fluorescence of Tricyanofuran Derivatives Containing a 2-Vinylphenol Fragment

Belikov M., Fedoseev S., Ievlev M., Ershov O.

摘要

Reaction of 5-substituted 2-hydroxybenzaldehydes with 2-[3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene]propanedinitrile (tricyanofuran) in ethanol in the presence of ammonium acetate afforded 2-{3-cyano-4-[(E)-2-(2-hydroxyphenyl)ethenyl]-5,5-dimethylfuran-2(5H)-ylidene}propanedinitriles which were found to exhibit solid state fluorescence with the emission maxima ranging from λ 594 to 640 nm. Chromophores containing an alkyl substituent in the benzene ring showed the most intense fluorescence.

Russian Journal of Organic Chemistry. 2019;55(10):1623-1625
pages 1623-1625 views

Efficient Microwave-Assisted Synthesis of Some N-Heterocycles Integrated with a Pyrazole Moiety

Ramadan S., El-Helw E.

摘要

An efficient and rapid synthesis of new heterocyclic compounds via reactions of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde thiosemicarbazone with some carbon electrophiles, namely dimethyl acetylenedicar-boxylate, maleic anhydride, and ω-bromoacetophenone, under microwave irradiation has been developed. The structure of the synthesized compounds was confirmed by their analytical and spectral data.

Russian Journal of Organic Chemistry. 2019;55(10):1626-1628
pages 1626-1628 views