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卷 53, 编号 2 (2017)

Article

Enantioselective addition of β-keto phosphinate to ω-nitrostyrene in the presence of optically active nickel(II) complex

Sibiryakova A., Reznikov A., Rybakov V., Klimochkin Y.

摘要

Synthesis was performed of individual methyl [(S,2R,3S)-4-nitro-1-oxo-1,3-diphenylbutan-2-yl]-(phenyl)phosphinate from racemic β-keto phosphinate and ω-nitrostyrene under the catalysis by nickel(II) complex with (1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine.

Russian Journal of Organic Chemistry. 2017;53(2):153-156
pages 153-156 views

Dithiophosphorylation of nerol and geraniol trimethylsilyl derivatives

Nizamov I., Terenzhev D., Nizamov I., Shumatbaev G., Batyeva E., Cherkasov R.

摘要

Reaction of tetraphosphorus decasulfide with О-(cis- and trans-3,7-dimethylocta-2,6-dien-1-yl)-trimethylsilanes affords О,О-bis(cis- and trans-3,7-dimethylocta-2,6-dien-1-yl) S-(trimethylsilyl)dithiophosphates.

Russian Journal of Organic Chemistry. 2017;53(2):157-159
pages 157-159 views

Chemical transformations of tetracyclo[3.3.1.13,7.01,3]decane (1,3-dehydroadamantane): IV. Reaction of 1,3-dehydroadamantane with dicarboxylic acids esters

Mokhov V., Butov G., Saad K.

摘要

Adamantylation of esters of dicarboxylic acids with 1,3-dehydroadamantane under mild conditions afforded in high yields diesters of (adamantan-1-yl)-substituted unsymmetrical dicarboxylic acids.

Russian Journal of Organic Chemistry. 2017;53(2):160-162
pages 160-162 views

Methylation of mono- and dicarboxylic acids with dimethyl carbonate catalyzed with binder-free zeolite NaY

Khusnutdinov R., Shchadneva N., Mayakova Y., Konovalova Y., Khazipova A., Kutepov B.

摘要

Synthesis of methyl mono- and dicarboxylates was developed consisting in treating the corresponding acids with dimethyl carbonate in the presence of a heterogenic catalyst, crystalline aluminosilicate whose mechanically strong granules to 90–95% were built of crystal aggregates of zeolite Y with modulus of about 5.0 in the Na-form. Optimum catalyst and reagents ratio and the reaction conditions were found for the preparation in high yields of methyl esters of mono- and dicarboxylic acids.

Russian Journal of Organic Chemistry. 2017;53(2):163-168
pages 163-168 views

Stereoselective synthesis of 2-aryl-4-en-1-ols, promising synthons for the preparation of oxygen heterocycles

Boev V., Moskalenko A., Belopukhov S., Nikonova G.

摘要

Reactions of arylacetic acids with N-methoxymethanamine afford corresponding Weinreb amides which at alkenylation with methallyl and prenyl bromides in the presence of (Me3Si)2NNa+ form unsaturated amides ArCHRCONMe(OMe) (R = CH2CMe=CH2, CH2C=CMe2). Amides readily react with BuLi and BnMgCl to give ketones ArCHRCOR' (R' = Bu, Bn). A stereoselective reduction of the latter with LiBH(s-Bu)3 leads to a quantitative formation of syn-isomers of 2-aryl-4-en-1-ols.

Russian Journal of Organic Chemistry. 2017;53(2):169-177
pages 169-177 views

Deamination of 3-(dialkylamino)-1,4-diarylhex-5-en-1-ynes during vacuum distillation

Chukhajian E., Shahkhatuni К., Chukhajian E., Ayrapetyan L., Panosyan G.

摘要

During vacuum distillation of 3-(dialkylamino) derivatives of 1,4-diphenyl- and 4-phenyl-1-(p-chlorophenyl) hex-5-en-1-ynes deamination occurs resulting in a high yield of p-diarylbenzenes. The amines transformation into terbenzenes is a domino-reaction: first step consists in the β-elimination of secondary amines with the generation of conjugated dienyne which via an electrocyclic reaction transforms into cyclic allene intermediate. The latter after 1,3- or 1,5-hydride shift quickly converts into the final reaction products.

Russian Journal of Organic Chemistry. 2017;53(2):178-183
pages 178-183 views

Aminomethylation of substituted pyrroles and 4,5,6,7-tetrahydroindoles with biogenic cyclic amines

Markova M., Sobenina L., Ushakov I., Ivanov A., Trofimov B.

摘要

Aminomethylation of 2-methyl(aryl)-, 2-aryl-3-alkylpyrroles, 4,5,6,7-tetrahydroindole and its 1-vinyl- and 1-benzyl-substituted derivatives with a mixture of 5% water-ethanol solution of formaldehyde and cyclic amine (pyrrolidine, piperazine, and morpholine) without catalyst at room temperature leads to the formation of the corresponding 2-aminomethylpyrroles and 2-aminomethyl-4,5,6,7-tetrahydroindoles in up to 92% yields. In reaction of 1-vinyl-4,5,6,7-tetrahydroindole with formaldehyde water solution and piperazine in a 60% yield 1,4-bis(1-vinyl-4,5,6,7-tetrahydroindol-2-yl)piperazine was obtained, a promising bifunctional monomer and a building block for the synthesis of new indole derivatives, in particular, of biologically active polymers. In the reaction of 2-methylpyrrole and 4,5,6,7-tetrahydroindole with formaldehyde and morpholine along with the С2-aminomethylation the 1-hydroxymethylation of the pyrrole ring was observed.

Russian Journal of Organic Chemistry. 2017;53(2):184-191
pages 184-191 views

Synthesis of N-substituted 1-hydroxypyrrolo[3,4-f]indol-5,7-diones

Chirkova Z., Kabanova M., Filimonov S., Sergeev S., Smirnova E., Sudzilovskaya T.

摘要

General methods were developed of the synthesis of N-substituted 1-hydroxypyrrolo[3,4-f]indole-5,7-diones using as initial compounds substituted 6-nitroisoindole-1,3-diones and 5-nitro-4-phenacylphtalic acids.

Russian Journal of Organic Chemistry. 2017;53(2):192-198
pages 192-198 views

Synthesis of 1-(arylsulfonyl)pyrrolidines from phenols and 1-[(4-chlorophenyl)sulfonyl]-2-ethoxypyrrolidine

Smolobochkin A., Anikina E., Gazizov A., Burilov A., Pudovik M.

摘要

Acid-catalyzed reaction of 1-[(4-chlorophenyl)sulfonyl]-2-ethoxypyrrolidine with phenols leads to the formation of new 1-(arylsulfonyl)pyrrolidines. The reaction proceeds under mild conditions and may be used as a convenient method for the synthesis of pyrrolidine-1-sulfonylarene derivatives containing a phenol fragment in the position 2.

Russian Journal of Organic Chemistry. 2017;53(2):199-202
pages 199-202 views

Furfuryl vinyl ethers in [4+2]-cycloaddition reactions

Apartsin K., Gusarova N., Trofimov B., Oparina L., Vysotskaya O., Stepanov A., Ushakov I.

摘要

For the first time [4+2]-cycloaddition reactions were carried out between furfuryl vinyl ethers and typical dienophiles and heterodienes proceeding in uncatalyzed conditions and resulting in previously unknown heterocyclic systems containing either free vinyloxy groups or furfuryl substituents. With maleic anhydride and maleimide furfuryl vinyl ethers afforded 1-(vinyloxyalkyl)tricyclodec-8-ene-3,5-diones in up to 72% yields, and with N-benzylideneaniline or acrolein the corresponding functionally substituted tetrahydroquinolines (yield up to 65%) or 3,4-dihydropyrans (yield 23–50%) were obtained.

Russian Journal of Organic Chemistry. 2017;53(2):203-209
pages 203-209 views

Synthesis and configuration of (arylamino)methylidene-3H-furan-2-ones

Osipov A., Anis’kov A., Yegorova A.

摘要

Convenient method of one-pot tricomponent synthesis of (arylamino)methylidene-3?-furan-2-ones was developed. Basing on combined spectral data and NOE-experiments the features of stereostructures of obtained arylaminomethylidenederivatives were revealed.

Russian Journal of Organic Chemistry. 2017;53(2):210-214
pages 210-214 views

Tricomponent domino synthesis of 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles

Ershov O., Lipin K., Eremkin A., Nasakin O., Sheverdov V., Fedorov P., Tafeenko V.

摘要

In reaction of tetracyanoethylene with ketones and HCl in 1,4-dioxane at 30–40°? 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles are formed.

Russian Journal of Organic Chemistry. 2017;53(2):215-221
pages 215-221 views

Catalytic synthesis and stereostructure of 1,2,3-trisubstituted decahydroisoquinolines

Reshetov P., Seller R., Golikov A., Skuratova M.

摘要

Liquid-phase catalytic reduction of 1,2,3-substituted 5,6,7,8-tetrahydroisoquinolinium perchlorates was investigated. The reaction proceeds stereodirectionally affording cis-decahydroisoquinolines. The probable scheme of reaction products formation is suggested. The structure of compounds obtained was established by IR and 13C NMR spectroscopy.

Russian Journal of Organic Chemistry. 2017;53(2):222-225
pages 222-225 views

Synthesis of hetarylquinolines proceeding from 2-[(2-methylquinolin-4-yl)sulfanyl]acetohydrazide substituted in the benzene ring

Aleksanyan I., Hambardzumyan L.

摘要

At intramolecular cyclization of phenylhydrazinocarbothioamide in alkaline and acidic media quinolyl-substituted triazoles and thiadiazoles are obtained. Quinolyl-substituted thiazolidines and thiazolidinones were obtained at interaction of phenylhydrazinocarbothioamides with bromoacetophenone and ethyl bromoacetate.

Russian Journal of Organic Chemistry. 2017;53(2):226-230
pages 226-230 views

1,3-dipolar cycloaddition of diazomethane to quinoid derivatives of pyrido[1,2-a]benzimidazole

Slabko O., Ageenko N., Denisenko V., Kaminskii V.

摘要

Reactions of diazomethane with quinone mono(di)imines and methylidene quinone imines of pyrido[1,2-a]benzimidazole series occurs by the route of 1,3-dipolar cycloaddition and leads to the formation of quinoid compounds, in particular, previously unknown heterocyclic structures of indazolo[7',6':4,5]imidazo-[2,1-j]quinoline, indazolo[7',6':4,5]imidazo[2,1-e]acridine, indazolo[4',5':4,5]imidazo[2,1-j]quinoline, and indazolo[4',5':4,5]imidazo[2,1-e]acridine.

Russian Journal of Organic Chemistry. 2017;53(2):231-235
pages 231-235 views

Synthesis of substituted 2-(thiophen-2-yl)-1H-imidazol-1-ols

Os’kina I., Tikhonov A.

摘要

Substituted 2-(thiophen-2-yl)-1H-imidazol-1-ols were synthesized by cyclization of the corresponding α-thienyl nitrones in alkaline medium. α-Thienyl nitrones were obtained by reaction of N-(1-hydroxyimine-1-R-propan-2-yl)hydroxylamines with thiophene-2-carbaldehyde in methanol. At boiling α-thienyl nitrones in methanol in the presence of sodium methylate 5-aryl(hetaryl)-2-(thiophen-2-yl)-1H-imidazol-1-ols are formed chemoselectively.

Russian Journal of Organic Chemistry. 2017;53(2):236-239
pages 236-239 views

New derivatives of 4,5-dihydro-1H-pyrazole, 4,5-dihydro-1,2-oxazole, and pyrimidine prepared proceeding from (E)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one

Potkin V., Petkevich S., Kletskov A., Kolesnik I., Zvereva T., Zhukovskaya N., Levkovskaya G., Rozentsveig I.

摘要

Condensation of acetylferrocene with 5-phenyl(4-methylphenyl)-1,2-oxazole-3-carbaldehydes afforded (Е)-3-[5-phenyl(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-ones. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with semicarbazide, thiosemicarbazide, and hydroxylamine led to the formation of 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole- 1-carboxamide, 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, and 5-(4-methylphenyl)-3'-ferrocenyl-4',5'-dihydro-3,5'-bi-1,2-oxazole respectively. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with guanidine and thiourea result in 4-[5-(4-methyl-phenyl)-1,2-oxazol-3-yl]-6-ferrocenylpyrimidin-2-amine and -2-thione respectively.

Russian Journal of Organic Chemistry. 2017;53(2):240-245
pages 240-245 views

Regio- and stereoselective (3 + 2)-cycloaddition of nitrile oxides and nitrones to N-vinylindole

Efremova M., Kostikov R., Larina A., Molchanov A.

摘要

1,3-Dipolar cycloaddition of nitrile oxides and nitrones to N-vinylindole proceeds regioselectively at the exocyclic multiple bond to form 5-indolyl-substituted isoxazolines and isoxazolidines in good yields.

Russian Journal of Organic Chemistry. 2017;53(2):246-250
pages 246-250 views

Synthesis of functionalized amides of 2-(arylamino)pyrimidine series

Ignatovich Z., Koroleva E.

摘要

New amides of 2-(arylamino)pyrimidine series were synthesized with pharmacophoric fragments of tyrosine kinase and histone deacetylase inhibitors and functional groups providing chemosorption of compounds on nanocarriers.

Russian Journal of Organic Chemistry. 2017;53(2):251-257
pages 251-257 views

Alkylation of 3-methyl-1H-acenaphtho[5,6-de]pyridazine

Omelichkin N., Minyaeva L., Mezheritskii V.

摘要

Alkylation of 3-methyl-1Н-acenaphtho[5,6]pyridazine with methyl and propyl iodides as well as with benzyl chloride in alkaline medium leads to the formation of the corresponding both N- and С-substituted pyridazine derivatives and also to the dimerization product of the initial compound. The ratio of obtained compounds depends on the used hydride, reaction temperature, and solvent.

Russian Journal of Organic Chemistry. 2017;53(2):258-262
pages 258-262 views

Synthesis of pyrimidinethiones and spiropyrans proceeding from Mannich ketones

Shchekina M., Tumskii R., Klochkova I., Anis’kov A.

摘要

New synthetic opportunities of conjugated and saturated β-aminoketones were revealed consisting in heterocyclization reactions with the formation of spirochromenes and hydropyrimidinethiones. Alicyclic conjugated Mannich bases under conditions of basic catalysis suffer deamination followed by [4+2]-cycloaddition leading to the stereo- and regiodirected formation of difficultly available spirochromene derivatives. Three-component condensation of acyclic and alicyclic Mannich ketones with thiourea and aromatic aldehydes under aprotic acid catalysis afforded functionalized derivatives of pyrimidine-2-thione series. Optimum conditions were found for О,N-heterocyclization of β-aminocarbonyl substrates.

Russian Journal of Organic Chemistry. 2017;53(2):263-269
pages 263-269 views

Fused pyrimidine systems: XVII. Arylsulfenylation of 5-allylpyrimidine-4(3H)-one derivatives. Synthesis of arylsulfanyl-substituted 5,6-dihydrofuro[2,3-d]- and 6,7-dihydro-5H-pyrano[2,3-d]pyrimidines

Vas’kevich A., Vovk M.

摘要

5-Allylpyrimidine-4-ones react with arylsulfenyl chlorides in dichloromethane with the formation of 5-[(2-arylsulfanyl)-3-chloropropyl]-pyrimidine-4-ones that under the action of sodium acetate undergo cyclization into 6-arylsulfanyl-6,7-dihydro-5H-pyrano[2,3-d]pyrimidines. At performing similar reactions in nitromethane an intramolecular electrophilic cyclization occurs affording 6-[(arylsulfanyl)methyl]-5,6-dihydrofuro[2,3-d]pyrimidines.

Russian Journal of Organic Chemistry. 2017;53(2):270-276
pages 270-276 views

Efficient synthesis of N-carboxyalkyl-substituted dithiaza- and dioxadithiazacycloalkanes by cyclocondensation of amino acids with formaldehyde and α,ω-dithiols

Khabibullina G., Fedotova E., Abdullin M., Tyumkina T., Akhmetova V., Ibragimov A.

摘要

A method of synthesis of N-carboxyalkyl-substituted dithiaza- and dioxadithiazacycloalkanes was developed consisting in a tricomponent [1+2+1]-cyclocondensation of amino acids with formaldehyde and aliphatic α,ω-dithiols (1,3-propane-, 1,4-butanedithiols, 3,6-dioxa-1,8-octanedithiol).

Russian Journal of Organic Chemistry. 2017;53(2):277-281
pages 277-281 views

Cyclopropanation and epoxidation of 2-ylidene derivatives of lupane series

Semenenko A., Babak N., Gella I., Musatov V., Shishkina S., Sofronov D., Lipson V.

摘要

Crotone condensation of allobetulone with fluorine-containing benzaldehydes afforded new α,β-unsaturated ketones of lupane series. Their transformations in reactions of reduction, oxidation, and cyclopropanation were investigated. The structures of the transformation products were established by X-ray diffraction analysis. The ability of obtained compounds to induce a cholesteric mesophase in nematic solvent 4'-pentyl-1,1'-biphenyl-4-carbonitrile was evaluated.

Russian Journal of Organic Chemistry. 2017;53(2):282-289
pages 282-289 views

Synthesis of monocationic β-cyclodextrin derivatives

Shipilov D., Kurochkina G., Levina I., Malenkovskaya M., Grachev M.

摘要

Reactions of 6-bromo- and 6-iodo-6-deoxy-β-cyclodextrin with organic amines of diverse nature afforded a series of monocationic derivatives with aminium groups located in the cyclodextrin scaffold on the side of the primary hydroxy groups. The structure and composition of the obtained cationic β-cyclodextrin derivatives were confirmed by 1H and 13C NMR data.

Russian Journal of Organic Chemistry. 2017;53(2):290-295
pages 290-295 views

Short Communications

Condensation of chloromethyl propargyl ether with nitriles

Talybov G.

摘要

Reactions of aromatic and aliphatic nitriles with chloromethyl propargyl ether in the presence of activated zinc followed by treatment with water in the presence of H3PMo12O40 afforded β-oxoethers.

Russian Journal of Organic Chemistry. 2017;53(2):296-298
pages 296-298 views

Methoxytelluration of styrene with tellurium tetrabromide

Musalova M., Musalov M., Potapov V., Amosova S.

摘要

Treating styrene with tellurium tetrabromide led to the formation of tribromo[(2-methoxy-2-phenyl)-ethyl]-λ4-tellane which was reduced with sodium metabisulfite results to bis[(2-methoxy-2-phenyl)ethyl]-ditelluride.

Russian Journal of Organic Chemistry. 2017;53(2):299-300
pages 299-300 views

Stereoselective addition of tellurium tetrachloride to 4-octyne

Musalova M., Musalov M., Potapov V., Amosova S.

摘要

Reaction of tellurium tetrachloride with 4-octyne occurs as an anti-addition and leads to the formation of trichloro[(Е)-1-propyl-2-chloropent-1-enyl]tellane which was reduced sodium metabisulfite in a two-phase system C6Н6–H2O affording bis[(Е)-1-propyl-2-chloropent-1-enyl]ditellane.

Russian Journal of Organic Chemistry. 2017;53(2):301-302
pages 301-302 views

Regiospecific allyl chlorination of betulin and diacetylbetulin

Kurskii Y., Bodrikov I., Chiyanov A., Bazhan L.

摘要

For the first time it was established that in the reaction of selenium dichloride with betulin and diacetylbetulin it is realized regiospecific allylic substitution of hydrogen in these alkenes by chlorine atom with formation of a single product–an unsaturated chloride of allylic type. The structure of products was proved by 1Н NMR spectra.

Russian Journal of Organic Chemistry. 2017;53(2):303-304
pages 303-304 views

Synthesis of pyrrole-dihydrothiazole ensembles from 1-allenyl-1H-pyrrole, isothiocyanates, and propargyl bromide

Tarasova O., Nedolya N., Albanov A., Trofimov B.

摘要

N-Alkylidene-1-(propargylsulfanyl)-2-(1H-pyrrol-1-yl)buta-1,3-dien-1-amines at treatment by a superbasic system t-BuONa–THF–DMSO under standard conditions of the synthesis of seven-membered azaheterocycles are chemo- and stereoselectively converted into 4,4-disubstituted 5-ethenylidene-2-[(Z)-1-(1H-pyrrol-1-yl)prop-1-enyl]-4,5-dihydro-1,3-thiazoles.

Russian Journal of Organic Chemistry. 2017;53(2):305-308
pages 305-308 views

Desilatranation of 1-organylsilatranes

Grebneva E., Bolgova Y., Trofimova O.

摘要

Reaction of phenyltrifluorosilane with 1-hydro- and 1-ethoxysilatranes proceeds with the cleavage of the F–Si bond and the formation of 1-fluorosilatrane. Under the action of alkylsilatranes also the cleavage of C–Si bond is observed with the formation of a minor product, 1-fluorosilatrane.

Russian Journal of Organic Chemistry. 2017;53(2):309-311
pages 309-311 views

New salt structures based on aminomethylated calix[4]-resorcinarenes and (1-hydroxyethane-1,1-diyl)bisphosphonic acid

Vagapova L., Nasirova Z., Burilova E., Zobov V., Burilov A., Amirov R., Pudovik M.

摘要

Aminomethylation of calix[4]resorcinarenes with (1-hydroxyethane-1,1-diyl)bisphosphonic acid afforded a series of new water soluble onium salts.

Russian Journal of Organic Chemistry. 2017;53(2):312-314
pages 312-314 views