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Том 54, № 8 (2018)

Article

Anthracene-Containing Podands, Ion-Active Molecular Switches of Fluorescence Characteristics

Bren’ V., Tolpygin I., Revinskii Y., Tikhomirova K., Dubonosov A.

Аннотация

2,2′-[Ethane-1,2-diylbis(oxy)]bis[N-(anthracen-9-ylmethyl)ethanamine] and its bisphenylthiourea and bisthiourea derivatives have been synthesized. The diamine, being a certain analog of an aza-crown ether with an open chain, exhibits a 50 times increase in the relative fluorescence intensity (off-on process) in the presence of cadmium(II) cations. Bis(phenylthiourea) is a bifunctional fluorophore sensitive to mercury(II) cations (emission flaring) and fluoride anions (emission quenching). Anions F, CN, H2PO4, and AcO lead to a practically complete quenching of the fluorescent properties of the bis(thiourea) (off-on process).

Russian Journal of Organic Chemistry. 2018;54(8):1117-1121
pages 1117-1121 views

Hydroxylamine Reactions with Peroxide Products of Alkenes Ozonolysis

Legostaeva Y., Garifullina L., Nazarov I., Ishmuratova N., Ishmuratov G.

Аннотация

Reactions were studied of peroxide ozonolysis products obtained from linear and cyclic alkenes with hydroxylamine prepared in situ from NH2OH·HCl by hydrogen chloride neutralization with sodium acetate. A one-pot reactions sequence was performed: alkene oxidation with ozone → reduction to a carbonyl compound with hydroxylamine → condensation of the carbonyl compound with hydroxylamine providing a possibility of direct transformation of alkenes in keto- and aldoximes excluding the stage of preparation and isolation of the carbonyl compound.

Russian Journal of Organic Chemistry. 2018;54(8):1122-1126
pages 1122-1126 views

Synthesis of N-(Adamantan-1-yl)carbamides by Ritter Reaction from Adamantan-1-ol and Nitriles in the Presence of Cu-Catalysts

Bayguzina A., Lutfullina A., Khusnutdinov R.

Аннотация

A selective synthesis of (Z)-N-(adamantan-1-yl)carbamides by the reaction of adamantan-1-ol and nitriles in the presence of Cu catalysts was carried out. Z-Conformation of amides is established basing on X-ray diffraction analysis and 2D NMR data.

Russian Journal of Organic Chemistry. 2018;54(8):1127-1133
pages 1127-1133 views

Structure and Rearrangements of 7-(Heptaphenylcycloheptatrienyl)isochalcogencyanates

Dushenko G., Mikhailov I., Mikhailova O., Minyaev R., Minkin V.

Аннотация

According to DFT B3LYP/6-31G(d,p) calculations, the intramolecular migration of NCX groups (X = O, S, Se, Te) in 7-(heptaphenylcycloheptatrienyl)isochalcogencyanates in the gas phase proceeds via the dissociation–recombination mechanism. Structures were found of transition states preceding the formation of tight ion pairs. High activation barriers to the migration of isochalcogencyanate groups (\(\Delta E{^\neq_{\rm{ZPE}}}\) 26.7, 21.3, 20.5, 19.3 kcal mol–1) originate from the existence of stable conformation of molecules with NCX groups located in the equatorial position and are in agreement with the data of dynamic NMR. For the transition of the molecule in the form favorable for the NCX group migration an inversion of the seven-membered ring and the rotation of the phenyl group are necessary.

Russian Journal of Organic Chemistry. 2018;54(8):1134-1147
pages 1134-1147 views

Synthesis of Benzyl Alkyl Ethers by Intermolecular Dehydration of Benzyl Alcohol with Aliphatic Alcohols under the Effect of Copper Containing Catalysts

Bayguzina А., Gimaletdinova L., Khusnutdinov R.

Аннотация

Synthesis of benzyl alkyl ethers was performed in high yields by intermolecular dehydration of benzyl and primary, secondary, tertiary alcohols under the effect of copper containing catalysts. The formation of benzyl alkyl ethers occurs with participation of benzyl cation.

Russian Journal of Organic Chemistry. 2018;54(8):1148-1155
pages 1148-1155 views

Synthesis of Potentially Bioactive 6-Bromobenzo[f]isoindolinium Bromides by Base-Catalyzed Intramolecular [4+2]-Cycloaddition

Chukhadzhian E., Gevorgyan H., Ayrapetyan L., Chukhadzhian E., Shahkhatuni K., Mkrtchyan A., Panosyan G.

Аннотация

Intramolecular cyclization of bromides of diethyl-, dipropyl-, and penthamethylenepropargyl[3-(4-bromophenyl)prop-2-ynyl]ammonium into 6-bromobenzo[f]isoindolinium bromides catalyzed with bases occurs with moderate self-heating. The morpholine analog even in more diluted solutions reacts with vigorous self-heating. Cyclization of dimethyl analog takes place only at heating at 80–85°C during 1 h.

Russian Journal of Organic Chemistry. 2018;54(8):1156-1160
pages 1156-1160 views

Three-Component Synthesis and Optical Properties of Nicotinic Acid Esters Containing Buta-1,3-dien-1,1,3-tricarbonitrile Fragment

Bardasov I., Alekseeva A., Chunikhin S., Ershov O.

Аннотация

Three-component synthesis of ethyl 4-aryl-2-methyl-5-cyano-6-(dicyanomethylidene)-1,6-dihydropyridine-3-carboxylates was developed consisting in the reaction of acetoacetic ester, aromatic aldehydes, and malononitrile dimer in the presence of sodium nitrite. Optical properties of synthesized compounds were investigated and it was demonstrated that they possessed intensive fluorescence in solution and in solid state with emission maxima in the yellow and green region of the visible light.

Russian Journal of Organic Chemistry. 2018;54(8):1161-1165
pages 1161-1165 views

One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium

Makhmutov A.

Аннотация

One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.

Russian Journal of Organic Chemistry. 2018;54(8):1166-1172
pages 1166-1172 views

Synthesis of Fused 2Н-Pyridin-2-ones under the Conditions of Multicomponent Hantzsch Reaction

Strashilina I., Arzyamova E., Fedotova O.

Аннотация

One-pot process was studied between a substituted 4-hydroxy-2Н-pyran-2-one and aromatic aldehydes and ammonium acetate in the conditions of modified Hantzsch reaction in acid environment under thermal and microwave activation. Arylmethylenebis-4-hydroxy-2Н-pyridin-2-ones, hydrochromenopyridinone, and their oxygen-containing heteroanalogs were isolated. A primary condensation was confirmed into bispyran-2-one adducts, and at the use of salicilaldehyde, into pyranochromene with subsequent recyclization of pyranone fragments in pyridinone ones.

Russian Journal of Organic Chemistry. 2018;54(8):1173-1178
pages 1173-1178 views

Ultrasound-Assisted Synthesis of 5H-Chromeno[2,3-b]pyridine Derivatives

Bardasov I., Alekseeva A., Bezgin D., Nasakin O., Ershov O.

Аннотация

An environmentally friendly method has been developed for the preparation of 5H-chromeno[2,3-b]pyridine derivatives in an aqueous medium under ultrasound irradiation.

Russian Journal of Organic Chemistry. 2018;54(8):1179-1183
pages 1179-1183 views

Mass Spectra of New Heterocycles. XVII. Main Fragmentation Routes of Molecular Ions of 4-Alkoxy-5-amino-3-methylthiophene-2-carbonitriles under Electron and Chemical Ionization

Klyba L., Nedolya N., Sanzheeva E., Tarasova O.

Аннотация

For the first time decomposition was investigated of 4-alkoxy-5-amino-3-methylthiophene-2-carbonitriles under the conditions of electronic (70 eV) and chemical (reagent gas methane) ionization. At the electronic ionization the compounds under study [except for 4-(1-ethoxyethoxy) and 4-(ferrocenylmethoxy) derivatives] form stable molecular ions that decompose mainly by the cleavage of an alkyl radical from the alkoxy-substituent. Further fragmentation of the arising ion [M–Alk]+ depends on the substituent nature in the amino group. In the mass spectrum of 4-(ferrocenylmethoxy)-substituted thiophene peaks of the ion [FcCH2]+ and its fragmentation products prevail. In the mass spectra of chemical ionization predominant peaks belong to ions M, [M + H]+ and [M + C2H5]+, and fragment ions are absent.

Russian Journal of Organic Chemistry. 2018;54(8):1184-1188
pages 1184-1188 views

Thermal Rearrangements of 3H- and 4H-Pyrazoles Prepared by Reactions of 9-Diazofluoren with Methyl Tetrolate and Methyl 3-Phenylpropiolate

Vasin V., Popkova Y., Bezrukova Y., Razin V., Somov N.

Аннотация

9-Diazofluoren adds in Et2O at 20°C to methyltetrolate in keeping with Auwers rule and nonregioselectively adds to methyl-3-phenylpropiolate with the formation of spirocyclic 3H-pyrazoles. The methyltetrolate adduct at boiling in toluene converts into methyl 3a-methyl-3aH-dibenzo[e,g]indazole-3-carboxylate, at 190°C in benzene, into methyl 3-methyl-2H-dibenzo[e,g]indazole-2-carboxylate, and at 160°C in methanol, into 3-methyl-2H-dibenzo[e,g]indazole. Auwers adduct of methyl 3-phenylpropiolate at boiling in benzene gives cyclopropene derivative and at boiling in methanol isomerizes into methyl 3a-phenyl-3aHdibenzo[e,g]indazole-3-carboxylate. Anti-Auwers adduct at boiling in benzene isomerizes into methyl 2-phenylpyrazolo[1,5-f]phenanthridine-3-carboxylate.

Russian Journal of Organic Chemistry. 2018;54(8):1189-1199
pages 1189-1199 views

Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole

Elchaninov M., Aleksandrov A.

Аннотация

Reaction of 1,2-diamino-4-nitrobenzene with furan-2-carbaldehyde in the presence of copper sulfate afforded 2-(furan-2-yl)-5(6)-nitro-1H-benzimidazole. Its N-methylation provided 1-methyl-5(6)-nitro isomers. After reduction of isomers with tin in conc. HCl a pure 3-methyl-2-(furan-2-yl)benzimidazol-5-amine was obtained. The condensation of this amine with acetic anhydride led to the formation of N-[3-methyl-2-(furan-2-yl)benzimidazol-5-yl]acetamide whose treatment with excess P2S5 in anhydrous pyridine resulted in the corresponding thioamide. The latter was oxidized with K3[Fe(CN)6] in alkaline environment to obtain 2,8-dimethyl-7-(furan-2-yl)-8H-imidazo[4,5-g][1,3]benzothiazole. Its reactions of electrophilic substitution were studied: nitration, bromination, sulfonation, formylation, acylation. The substituent is introduced exclusively in the position 5 of the furan ring.

Russian Journal of Organic Chemistry. 2018;54(8):1200-1204
pages 1200-1204 views

Nitration of 3-Methylaceperidazines with a Large Excess of Fuming Nitric Acid

Omelichkin N., Minyaeva L., Milov A., Kuz’mina L., Mezheritskii V.

Аннотация

Nitration of N-acetyl-3-methylaceperidazine with a 2–3-fold excess of nitric acid (d 1.36, 1.48) in glacial acetic acid results in the exclusive formation of mono- and dinitroderivatives. The nitration of 3-methylaceperidazine and its N-alkyl- and N-acetyl-substituted derivatives with a 6–9-fold excess of fuming nitric acid (d 1.54) in the same conditions results in the formation of both the expected products of mono- and dinitration and a product of the electrophilic addition of nitric acid to a double bond of acenaphthene scaffold of the molecule of nitration product.

Russian Journal of Organic Chemistry. 2018;54(8):1205-1212
pages 1205-1212 views

Formation of N–S Bonds in Reactions of 2-[2-Oxo-1-(tosyloxyimino)-2-phenylethyl]pyrimidin-4(3H)-one and Its 6-derivatives with Thiourea and Potassium Thiocyanate

Yavolovskii A., Ivanov Y., Grishchuk L., Kravtsov V., Fonar’ M., Kamalov G.

Аннотация

Reaction of potassium thiocyanate with 2-[2-oxo-1-(1-tosyloxyimino)-2-phenylethyl]pyrimidin-4-(3H)-one derivatives led to the formation of a new fused heterocyclic system with a common nitrogen atom, substituted 7H-[1,2,5]thiadiazolo[2,3-a]pyrimidin-7-one.

Russian Journal of Organic Chemistry. 2018;54(8):1213-1217
pages 1213-1217 views

Synthesis of New Amides of Isoxazole- and Isothiazole-Substituted Carboxylic Acids Containing an Arylaminopyrimidine Fragment

Ignatovich Z., Ermolinskaya A., Kletskov A., Potkin V., Koroleva E.

Аннотация

By acylation of substituted 2-aminoarylpyrimidines with 5-phenyl(p-tolyl)isoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides new amides of pyrimidine series were obtained.

Russian Journal of Organic Chemistry. 2018;54(8):1218-1222
pages 1218-1222 views

New Reactions of (2-Aminophenyl)diphenylmethanol with Carbonyl Compounds

Gromachevskaya E., Pushkareva K., Bespalov A., Strelkov V.

Аннотация

Reactions of (2-aminophenyl)diphenylmethanol with ketones (dimedone, camphor, and 3-bromocamphor) in acetic acid result in the formation of arylimines of camphore and 3-bromocamphore, substituted tetrahydroacridin-1(2H)-one and 2-methyl-4,4-diphenylbenzoxazine.

Russian Journal of Organic Chemistry. 2018;54(8):1223-1227
pages 1223-1227 views

Alkylation of 2-Sulfanylbenzoxazole with α-Iodoketones in the Absence of Bases

Shagun L., Dorofeev I., Zhilitskaya L., Yarosh N., Larina L.

Аннотация

Reaction of 2-sulfanylbenzoxazole with 1-iodopropan-2-one, 2-iodo-1-phenylethanone, and 2-iodo-1-(thiophen-2-yl)ethanone without solvent and bases afforded bis(benzoxazol-2-yl)disulfonium derivatives in a single preparative stage. The reaction proceeds as a domino-process and includes the alkylation of a sulfanyl group of benzoxazole, the reduction of iodoketone with hydrogen iodide, the oxidation of 2-sulfanylbenzoxazole to disulfide, the alkylation of disulfide atoms of sulfur, and the formation of triiodideanions. The yield of disulfonium derivatives increases twice in the presence of equimolar amount of iodine.

Russian Journal of Organic Chemistry. 2018;54(8):1228-1231
pages 1228-1231 views

Synthesis of 2-[3-Aryl-3-(5-phenylisoxazol-3-yl)propyl] Derivatives of 5,5-Dimethylcyclohexane- and Cyclopenthane-1,3-diones Proceeding from 2-(4-Nitro-3-arylbutyl) Precursors

Dontsu Y., Pashkovskii F., Rubinov D., Lakhvich F.

Аннотация

Regiospecific reduction of carbonyl group of acyl chain in the previously described 4-nitro-3-arylbutanoyl derivatives of dimedone and cyclopentane-1,3-dione was performed. On the basis of nitromethyl group of the enol derivatives of the reduction products obtained from the mentioned compounds nitrile oxide intermediates were prepared, which in situ reacted with phenylacetylene to form the corresponding isoxazole derivatives.

Russian Journal of Organic Chemistry. 2018;54(8):1232-1240
pages 1232-1240 views

Synthesis and Chemical Transformations of 5-Alkyl(phenyl)-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-7-oles

Zemlyanaya N., Karnozhitskaya T., Musatov V., Konovalova I., Shishkina S., Lipson V.

Аннотация

5,5,7-Trimethyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-7-ol was synthesized by cyclocondensation of 3-amino-1,2,4-triazole with 4-methylpent-3-en-2-one; its chemical transformations, and also the transformations of 5-phenyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidin-7-ol were investigated in reactions with reagents of diverse electronic nature.

Russian Journal of Organic Chemistry. 2018;54(8):1241-1249
pages 1241-1249 views

One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Using Catalytic System NaOH‒DMSO

Pankrat’eva V., Sharonova T., Tarasenko M., Baikov S., Kofanov E.

Аннотация

One-pot convenient process was developed for the production of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with anhydrides or acyl chlorides in a system NaOH‒DMSO. The reaction proceeds at room temperature with high yields.

Russian Journal of Organic Chemistry. 2018;54(8):1250-1255
pages 1250-1255 views

Short Communications

Three-Component Stereoselective Synthesis of (1R,2S)-1-Aryl-2-{[prop-2-yn(en)yloxy]methyl}spiro[2,4]hepta-4,7-diones

Talybov G.

Аннотация

Three-component reaction involving cyclopentane-1,3-dione, substituted benzaldehydes, and chloromethyl propyn(en)yl ethers results in a stereoselective formation of trans-1-aryl-2-{[prop-2-(yn)enyloxy]-methyl}spiro[2,4]hepta-4,7-diones in satisfactory yields.

Russian Journal of Organic Chemistry. 2018;54(8):1256-1259
pages 1256-1259 views

Synthesis of 4-Methyl-2,6-di(9H-thioxanthen-9-yl)aniline

Gorokhov V., Gorokhova S., Lystsova E.

Аннотация

4-Methyl-2,6-di(9H-thioxanthen-9-yl)aniline was synthesized by the reaction of 4-methylaniline with N-thioxanthenylpyridinium perchlorate in a 1: 3 ratio at short heating.

Russian Journal of Organic Chemistry. 2018;54(8):1260-1261
pages 1260-1261 views

Regioselective Reaction of Pyridine-2-Sulfenyl Chloride with Isoeugenol

Ishigeev R., Potapov V., Amosova S.

Аннотация

Proceeding from 2,2′-disulfanediyldipyridine and isoeugenol a regioselective one-pot synthesis was developed affording 3-(4-hydroxy-3-methoxyphenyl)-2-methyl-2H,3H-[1,3]thiazolo[3,2-a]pyridin-4-ium chloride in a 70% yield.

Russian Journal of Organic Chemistry. 2018;54(8):1262-1264
pages 1262-1264 views

3-Polyfluoroalkyl-1,5-diphenylpyrazoles in Suzuki Cross-Coupling Reactions

Ivanova А., Burgart Y., Saloutin V.

Аннотация

Suzuki cross-coupling was used for modification of 3-polyfluoroalkyl-1-phenylpyrazoles at the position C4. The synthesized 4-bromo- and 4-phenyl derivatives showed antitubercular effect on pyrazinamide level.

Russian Journal of Organic Chemistry. 2018;54(8):1265-1267
pages 1265-1267 views

Mercuration of a Terminal Triple Bond of Substituted Azoles

Hobosyan N., Balyan K., Petrosyan A., Sargsyan A., Chobanyan Z., Nersisyan H.

Аннотация

Mercuration of a terminal triple bond in pirazoles and triazoles derivatives in the presence of acetylacetone followed by demercuration of intermediates by NaBH4 afforded heterocyclic oxoenol derivatives.

Russian Journal of Organic Chemistry. 2018;54(8):1268-1269
pages 1268-1269 views

Synthesis of 4-Amino-1,2,4-triazines from Esters of Aroylpyruvic Acids and Thiocarbohydrazide

Kobelev A., Stepanova E., Maslivets A.

Аннотация

Esters of aroylpyruvic acids regioselectively react with thiocarbohydrazide to afford substituted 4-amino-1,2,4-triazines.

Russian Journal of Organic Chemistry. 2018;54(8):1270-1271
pages 1270-1271 views

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