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Single-Electron Transfer in the Reaction of Red Phosphorus with 4-(Phenylsulfanyl)benzophenones in Superbase Systems MOH/DMSO MOH/DMSO超碱体系中红磷与4-（苯基磺酰）二苯甲酮反应的单电子转移
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602705
V. A. Kuimov, R. I. Fattakhov, N. I. Tikhonov, N. A. Belogorlova
{"title":"Single-Electron Transfer in the Reaction of Red Phosphorus with 4-(Phenylsulfanyl)benzophenones in Superbase Systems MOH/DMSO","authors":"V. A. Kuimov,&nbsp;R. I. Fattakhov,&nbsp;N. I. Tikhonov,&nbsp;N. A. Belogorlova","doi":"10.1134/S1070428025602705","DOIUrl":"10.1134/S1070428025602705","url":null,"abstract":"<p>Red phosphorus reacted with 4-(phenylsulfanyl)- and bis(4-phenylsulfanyl)benzophenones in superbase suspensions MOH/DMSO (M = Na, K) on heating at (85°C, 1.5–4 h, argon atmosphere) according to the single-electron transfer mechanism. The formation of potassium bis{phenyl[4-(phenylsulfanyl)phenyl]­methyl} phosphate radical anion was detected by ESR spectroscopy. Reduction products of the initial (phenylsulfanyl)benzophenones (diarylmethanols and diarylmethanes functionalized with phenylsulfanyl groups) and diphenyl disulfide were isolated from the reaction mixtures, while potassium bis{phenyl[4-(phenylsulfanyl)phenyl]methyl} and bis{di[4-(phenylsulfanyl)phenyl]methyl} phosphates were detected among the products and identified by NMR spectroscopy).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1216 - 1223"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868924","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of (1,2,4-Triazinyl)furazans （1,2,4-三嗪基）呋喃唑的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602298
A. A. Larin, A. V. Shaferov, I. V. Ananyev, L. L. Fershtat
{"title":"Synthesis of (1,2,4-Triazinyl)furazans","authors":"A. A. Larin,&nbsp;A. V. Shaferov,&nbsp;I. V. Ananyev,&nbsp;L. L. Fershtat","doi":"10.1134/S1070428025602298","DOIUrl":"10.1134/S1070428025602298","url":null,"abstract":"<p>4-Methyl- and 4-amino-1,2,5-oxadiazole-3-carbohydrazonamides reacted with glyoxal to give the corresponding dimeric products, <i>N</i>′,<i>N</i>″-(ethane-1,2-diylidene)bis(4-R-1,2,5-oxadiazole-3-carbohydrazonamides) (R = Me, NH<sub>2</sub>), whereas the reaction of the same substrates with other 1,2-dicarbonyl compounds, such as benzil and ninhydrin afforded target 3-(4-R-1,2,5-oxadiazol-3-yl)-1,2,4-triazine derivatives. The product structure was confirmed by IR and NMR spectra and X-ray analysis. The synthesized compounds are promising as scaffolds for the design of pharmacologically active compounds with different kinds of activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1311 - 1318"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868947","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Reaction of 5,7-Dihydroxycoumarins with Pyrimidines 5,7-二羟基香豆素与嘧啶的反应
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602134
R. F. Fatykhov, I. A. Khalymbadzha, A. P. Potapova, V. V. Melekhin, A.V. Paramonova, D. S. Kopchuk, P. A. Slepukhin, V. G. Kartsev, O. N. Chupakhin
{"title":"Reaction of 5,7-Dihydroxycoumarins with Pyrimidines","authors":"R. F. Fatykhov,&nbsp;I. A. Khalymbadzha,&nbsp;A. P. Potapova,&nbsp;V. V. Melekhin,&nbsp;A.V. Paramonova,&nbsp;D. S. Kopchuk,&nbsp;P. A. Slepukhin,&nbsp;V. G. Kartsev,&nbsp;O. N. Chupakhin","doi":"10.1134/S1070428025602134","DOIUrl":"10.1134/S1070428025602134","url":null,"abstract":"<p>The study of 5,7-dihydroxycoumarins as nucleophilic agents in the S<sub>N</sub><sup>H</sup> reaction with pyrimidines showed that the reaction does not stop at the stage of formation of σ<sup>H</sup>-adduct as intermediate in the S<sub>N</sub><sup>H</sup> mechanism but proceeds further with annulation of the 1,3,5-oxadiazocine ring in moderate to excellent yields. The structures of the obtained compounds were confirmed by NMR spectroscopy and X-ray diffraction. A primary in vitro assessment of their antitumor activity was performed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1296 - 1303"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868590","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Regioselective Synthesis of Furfuryl-Substituted 1,2,3-Triazoles by 1,3-Dipolar Cycloaddition of 5-(Azidomethyl)furfural to Methyl Alka-2,3-dienoates 5-（叠氮多甲基）糠醛1,3-偶极环加成至甲基碱-2,3-二烯酸甲酯的区域选择性合成呋喃取代1,2,3-三唑
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025603292
G. M. Gindullina, G. F. Sakhautdinova, I. M. Sakhautdinov
{"title":"Regioselective Synthesis of Furfuryl-Substituted 1,2,3-Triazoles by 1,3-Dipolar Cycloaddition of 5-(Azidomethyl)furfural to Methyl Alka-2,3-dienoates","authors":"G. M. Gindullina,&nbsp;G. F. Sakhautdinova,&nbsp;I. M. Sakhautdinov","doi":"10.1134/S1070428025603292","DOIUrl":"10.1134/S1070428025603292","url":null,"abstract":"<p>A procedure has been proposed for the regioselective synthesis of new 1,2,3-triazole derivatives from methyl alka-2,3-dienoates. The effect of substituents in the initial reactants on the regio- and stereo­selectivity of the reaction has been studied, and the synthesized compounds have been characterized by physicochemical methods. Regioselective 1,3-dipolar cycloaddition of 5-(azidomethyl)furfural [prepared from 5-(chloromethyl)furfural] to alka-2,3-dienoates containing a cyclic imide fragment in toluene afforded substituted 1,2,3-triazoles with maximum remoteness of the furfuryl and ester groups from each other, which minimizes steric repulsion.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1369 - 1373"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144869032","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Self-Assembly of Pyrrole-Centered Pentaheterocyclic Ensembles in the System Hetarenecarbonitrile/Ethynylhetarene/t-BuOK/DMSO 以吡咯为中心的五杂环体系的自组装（英文）
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602663
E. Yu. Schmidt, N. A. Lobanova, I. V. Tatarinova, I. A. Ushakov, B. A. Trofimov
{"title":"Self-Assembly of Pyrrole-Centered Pentaheterocyclic Ensembles in the System Hetarenecarbonitrile/Ethynylhetarene/t-BuOK/DMSO","authors":"E. Yu. Schmidt,&nbsp;N. A. Lobanova,&nbsp;I. V. Tatarinova,&nbsp;I. A. Ushakov,&nbsp;B. A. Trofimov","doi":"10.1134/S1070428025602663","DOIUrl":"10.1134/S1070428025602663","url":null,"abstract":"<p>Pyrrole-centered pentaheterocyclic ensembles, tetrasubstituted 1<i>H</i>-pyrroles with fundamental hetero­cycles (pyrrole, furan, thiophene, pyridine) in various combinations, have been synthesized in up to 60% by the reaction of hetarenecarbonitriles with ethynylhetarenes in the system <i>t</i>-BuOK/DMSO (room temperature, 1 h). The reaction involves cascade self-assembly of three ethynylhetarene molecules and one hetarenecarbo­nitrile molecule, which is triggered and driven by acetylide anions.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1279 - 1285"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Methylene-Bridged Blocks Based on Thieno[3,2-b]pyrrole and Indole 基于噻吩[3,2-b]吡咯和吲哚的新型亚甲基桥嵌段
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602626
S. A. Torosyan, Z. F. Nuriakhmetova, F. A. Gimalova, M. S. Miftakhov
{"title":"New Methylene-Bridged Blocks Based on Thieno[3,2-b]pyrrole and Indole","authors":"S. A. Torosyan,&nbsp;Z. F. Nuriakhmetova,&nbsp;F. A. Gimalova,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428025602626","DOIUrl":"10.1134/S1070428025602626","url":null,"abstract":"<p>The condensation of (4-benzylthieno[3,2-<i>b</i>]pyrrol-5-yl)methanols with indole in methylene chloride in the presence of Amberlyst 15 afforded new 2-[(4-benzyl-4<i>H</i>-thieno[3,2-<i>b</i>]pyrrol-5-yl)methyl]-1<i>H</i>-indoles.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1374 - 1378"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New (2,2′-Bi)pyridines with Higher Amine Substituents. Synthesis and Properties 具有高胺取代基的新型（2,2′-双）吡啶。合成与性能
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602067
A. Rammohan, G. A. Kim, A. P. Krinochkin, Ya. K. Shtaitz, S. E. Vatolina, A. V. Baklykov, T. A. Tseitler, D. S. Kopchuk, G. V. Zyryanov
{"title":"New (2,2′-Bi)pyridines with Higher Amine Substituents. Synthesis and Properties","authors":"A. Rammohan,&nbsp;G. A. Kim,&nbsp;A. P. Krinochkin,&nbsp;Ya. K. Shtaitz,&nbsp;S. E. Vatolina,&nbsp;A. V. Baklykov,&nbsp;T. A. Tseitler,&nbsp;D. S. Kopchuk,&nbsp;G. V. Zyryanov","doi":"10.1134/S1070428025602067","DOIUrl":"10.1134/S1070428025602067","url":null,"abstract":"<p>An efficient synthetic approach to (2,2′-bi)pyridines containing higher alkylamino groups at the α-positions has been proposed on the basis of their 1,2,4-triazine precursors. The synthetic sequence included solvent-free reactions. The synthesized compounds in acetonitrile solution showed photoluminescence with an absolute quantum yield of up to 83.2 %.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1286 - 1291"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Synthesis of N-Monosubstituted Propane-1,3-diamines n -单取代丙烷-1,3-二胺的新合成方法
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602717
G. S. Martyanov, M. A. Barabanov, A. R. Gindullin, P. A. Slepukhin, A. V. Pestov
{"title":"New Synthesis of N-Monosubstituted Propane-1,3-diamines","authors":"G. S. Martyanov,&nbsp;M. A. Barabanov,&nbsp;A. R. Gindullin,&nbsp;P. A. Slepukhin,&nbsp;A. V. Pestov","doi":"10.1134/S1070428025602717","DOIUrl":"10.1134/S1070428025602717","url":null,"abstract":"<p>A new method has been proposed for the synthesis of N-monosubstituted 1,3-diamines through the protection of propane-1,3-diamine with phthalic anhydride in one step to produce 3,4-dihydropyrimido[2,1-<i>a</i>]­isoindol-6(2<i>H</i>)-one which is selectively alkylated at the imine nitrogen atom, followed by hydrolytic removal of the phthalyl protecting group. The target N-monosubstituted propane-1,3-diamines are thus obtained in up to 66% yield without formation of polyalkyl derivatives. A number of new compounds have been characterized; in particular, 1-methyl-6-oxo-2,3,4,6-tetrahydropyrimido[2,1-<i>a</i>]izoindol-1-ium iodide and its partial hydrolysis product, 3-(1,3-dioxo-1,3-dihydro-2<i>H</i>-isoindol-2-yl)-<i>N</i>-methylpropan-1-aminium iodide, have been studied by X-ray analysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1224 - 1235"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868720","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Trifluoromethyl-Substituted Imidazolidine-2-thiones and Their Reactions with Urea, 2-Aminoethanol, and 2-Aminophenol 三氟甲基取代咪唑烷-2-硫酮的合成及其与尿素、2-氨基乙醇和2-氨基苯酚的反应
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602699
L. V. Saloutina, M. I. Kodess, I. N. Ganebnykh, V. I. Saloutin, O. N. Chupakhin
{"title":"Synthesis of Trifluoromethyl-Substituted Imidazolidine-2-thiones and Their Reactions with Urea, 2-Aminoethanol, and 2-Aminophenol","authors":"L. V. Saloutina,&nbsp;M. I. Kodess,&nbsp;I. N. Ganebnykh,&nbsp;V. I. Saloutin,&nbsp;O. N. Chupakhin","doi":"10.1134/S1070428025602699","DOIUrl":"10.1134/S1070428025602699","url":null,"abstract":"<p>Perfluorobiacetyl reacted with thiourea, <i>N</i>-methylthiourea, and <i>N</i>-phenylthiourea in acetonitrile to give 92–95% of <i>cis</i>/<i>trans</i>-isomeric 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione and 1-methyl­(phenyl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thiones. The reaction of 4,5-dihy­droxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with 2-aminoethanol produced sulfanylideneimidazothiazolone, whereas the expected imidazooxazinethione was formed as a minor product. An unusual pathway was observed in the reaction of <i>N</i>-methylimidazolidine-2-thione with 2-aminoethanol, which afforded thiohydantoins, 5-[(2-hydroxyethyl)amino]-3-methyl-2-sulfanylidene-5-(trifluoromethyl)imidazolidin-4-one and 5-hydroxy-3-methyl-2-sulfanylidene-5-(trifluoromethyl)imidazolidin-4-one. <i>N</i>-Methylsulfanylideneimidazooxazolone and <i>N</i>-methyl(trifluoromethyl)thiohydantoin were formed instead of the expected thioglycoluril derivative in the reaction of <i>N</i>-methylimidazolidine-2-thione with urea. Heating of 4,5-dihydroxy-1-phenyl-4,5-bis(tri­fluoro­methyl)imidazolidine-2-thione with urea, 2-aminoethanol, or 2-aminophenol in <i>N</i>,<i>N</i>-dimethylacetamide led to the formation of intramolecular rearrangement product, <i>N</i>-phenyl-bis(trifluoromethyl)thiohydantoin.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1242 - 1253"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868719","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Chiral Bicyclic Pyrrolidine Block for Nirmatrelvir and Its Analogues 新的手性双环吡咯烷阻断剂用于Nirmatrelvir及其类似物
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602833
G. R. Sunagatullina, G. A. Shavaleeva, Z. R. Valiullina, M. S. Miftakhov
{"title":"New Chiral Bicyclic Pyrrolidine Block for Nirmatrelvir and Its Analogues","authors":"G. R. Sunagatullina,&nbsp;G. A. Shavaleeva,&nbsp;Z. R. Valiullina,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428025602833","DOIUrl":"10.1134/S1070428025602833","url":null,"abstract":"<p>(1<i>R</i>,5<i>S</i>)-2-Ethoxy-6,6-dimethyl-3-azabicyclo[3.1.0]hex-2-ene easily available from (+)-3-carene has been proposed as a key building block for the synthesis of Nirmatrelvir and related compounds. It has been obtained by enol ethylation of (1<i>R</i>,5<i>S</i>)-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-one with triethyloxonium tetra­fluoroborate.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1379 - 1383"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868946","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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