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Russian Journal of Organic Chemistry最新文献

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Synthesis, Structure, and Thermochemical and Electrochemical Properties of Schiff Bases of the Pyridine and Quinoline Series 吡啶和喹啉类席夫碱的合成、结构、热化学和电化学性质
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025603310
A. A. Perepechay, A. P. Krinochkin, A. V. Sukhov, E. A. Kudryashova, A. V. Gerasimov, V. S. Gaviko, D. V. Tkachenko, D. S. Kopchuk, G. V. Zyryanov, D. G. Yakhvarov
{"title":"Synthesis, Structure, and Thermochemical and Electrochemical Properties of Schiff Bases of the Pyridine and Quinoline Series","authors":"A. A. Perepechay,&nbsp;A. P. Krinochkin,&nbsp;A. V. Sukhov,&nbsp;E. A. Kudryashova,&nbsp;A. V. Gerasimov,&nbsp;V. S. Gaviko,&nbsp;D. V. Tkachenko,&nbsp;D. S. Kopchuk,&nbsp;G. V. Zyryanov,&nbsp;D. G. Yakhvarov","doi":"10.1134/S1070428025603310","DOIUrl":"10.1134/S1070428025603310","url":null,"abstract":"<p>A procedure has been proposed for the synthesis of pyridine and quinoline Schiff bases from the corresponding aldehydes and amines, which afforded the target products in more than 85% yield. Thermal decomposition pathways of the synthesized compounds have been identified by GC/MS and TG/DSC-MS analysis. They involve elimination of the hydrocarbon substituent from the imine fragment or the entire azomethine group with the formation of cationic 3-phenylpyridine and 6-substituted quinoline species. Cyclic voltammetric study of the title compounds has shown that their electrochemical reduction/oxidation is an ir­reversible process leading to fragmentation of the substrate molecules.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1342 - 1351"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144869030","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
Carbonylation of Perfluorinated Propenylbenzenes, Indenes, and 1-Alkylideneindans in Antimony Pentafluoride 全氟丙烯苯、茚和1-烷基烯茚在五氟化锑中的羰基化
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025603322
Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova
{"title":"Carbonylation of Perfluorinated Propenylbenzenes, Indenes, and 1-Alkylideneindans in Antimony Pentafluoride","authors":"Ya. V. Zonov,&nbsp;V. M. Karpov,&nbsp;T. V. Mezhenkova","doi":"10.1134/S1070428025603322","DOIUrl":"10.1134/S1070428025603322","url":null,"abstract":"<p>The carbonylation of perfluorinated 3-arylpropenes ArCF<sub>2</sub>CF=CF<sub>2</sub> (Ar = C<sub>6</sub>F<sub>5</sub>, 3-CF<sub>3</sub>C<sub>6</sub>F<sub>4</sub>) in SbF<sub>5</sub> under atmospheric CO pressure at room temperature, followed by treatment of the reaction mixture with water or methanol, afforded (<i>Z</i>)-perfluoro-2-arylbut-2-enoic acids or their methyl esters, respectively. In contrast, perfluoro-2-phenylpropene failed to undergo carbonylation under similar conditions. Perfluorinated 3-methyl-1<i>H</i>-indene and 1-methylidene- and 1-ethylideneindanes in antimony pentafluoride added two carbon monoxide molecules, and the subsequent treatment of the reaction mixture with methanol gave dimethyl perfluoro-1-alkyl-1<i>H</i>-indene-1,3-dicarboxylate as the major carbonylation product.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1359 - 1368"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144869031","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
A New Approach to 2,2′-Bipyridines with a Triptycen-2-amine Fragment 用雷公藤烯-2-胺片段合成2,2 ' -联吡啶的新方法
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602110
S. S. Potapova, M. I. Valieva, E. A. Kudryashova, D. S. Kopchuk, T. A. Pospelova, G. V. Zyryanov
{"title":"A New Approach to 2,2′-Bipyridines with a Triptycen-2-amine Fragment","authors":"S. S. Potapova,&nbsp;M. I. Valieva,&nbsp;E. A. Kudryashova,&nbsp;D. S. Kopchuk,&nbsp;T. A. Pospelova,&nbsp;G. V. Zyryanov","doi":"10.1134/S1070428025602110","DOIUrl":"10.1134/S1070428025602110","url":null,"abstract":"<p>An efficient synthetic approach to 2,2′-bipyridines with a triptycen-2-ylamino [(9<i>R</i>,10<i>R</i>)-9,10-di­hydro-9,10-[1,2]benzenoanthracen-2-ylamino] substituent at the α-position has been developed on the basis of 1,2,4-triazine precursors. The synthesis includes nucleophilic substitution of the cyano group in 3-(pyridine-2-yl)-1,2,4-triazine-carbonitriles, followed by the Boger reaction with norbornadiene.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1292 - 1295"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868592","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
Three-Component Cyclization of Phenyl 1,3-Dicarbonyls with α,β-Enaldehydes and 2-(Aminomethyl)aniline to Pyrido[2,1-b]quinazolines 苯基1,3-二羰基与α，β-烯醛和2-（氨基甲基）苯胺的三组分环化合成吡啶[2,1-b]喹唑啉
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602729
S. O. Kushch, M. V. Goryaeva, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, O. V. Koryakova, I. N. Ganebnykh, V. I. Saloutin
{"title":"Three-Component Cyclization of Phenyl 1,3-Dicarbonyls with α,β-Enaldehydes and 2-(Aminomethyl)aniline to Pyrido[2,1-b]quinazolines","authors":"S. O. Kushch,&nbsp;M. V. Goryaeva,&nbsp;Ya. V. Burgart,&nbsp;M. A. Ezhikova,&nbsp;M. I. Kodess,&nbsp;P. A. Slepukhin,&nbsp;O. V. Koryakova,&nbsp;I. N. Ganebnykh,&nbsp;V. I. Saloutin","doi":"10.1134/S1070428025602729","DOIUrl":"10.1134/S1070428025602729","url":null,"abstract":"<p>The three-component condensation of phenyl-substituted 1,3-dicarbonyl compounds, α,β-un­saturated aldehydes, and 2-(aminomethyl)aniline under mild conditions resulted in regio- and chemoselective formation of tetrahydro-7<i>H</i>-pyrido[2,1-<i>b</i>]quinazoline derivatives as mixtures of <i>trans</i> and <i>cis</i> diastereomers, most of which were isolated as individual isomers. Their steric structure was determined by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, including two-dimensional <sup>1</sup>H–<sup>13</sup>C HSQC/HMBC and <sup>1</sup>H–<sup>1</sup>H NOESY experiments, as well as by X-ray analysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1205 - 1215"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868715","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, Molecular Structure, and Spectral Properties of Ethyl 3-Oxo-2-(2,4,6-trinitrophenyl)butanoate 3-氧-2-（2,4,6-三硝基苯）丁酸乙酯的合成、分子结构和光谱性质
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025603176
D. A. Kazantsev, A. A. Denisov, M. S. Valova, P. A. Slepukhin, A. V. Pestov
{"title":"Synthesis, Molecular Structure, and Spectral Properties of Ethyl 3-Oxo-2-(2,4,6-trinitrophenyl)butanoate","authors":"D. A. Kazantsev,&nbsp;A. A. Denisov,&nbsp;M. S. Valova,&nbsp;P. A. Slepukhin,&nbsp;A. V. Pestov","doi":"10.1134/S1070428025603176","DOIUrl":"10.1134/S1070428025603176","url":null,"abstract":"<p>A preparative procedure has been developed for the synthesis of ethyl 3-oxo-2-(2,4,6-trinitrophenyl)­butanoate in an overall yield of 76% under mild conditions from commercially available picric acid and ethyl acetoacetate. The product structure was confirmed by X-ray analysis and <sup>1</sup>H NMR spectroscopy. The UV spectroscopic data revealed that the title compound is capable of intramolecular charge transfer.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1199 - 1204"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868716","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
Alternative Pathways in Cesium Carbonate-Promoted Reactions of tert-Butyl 2-[(Diphenylmethylidene)amino]acetate with 2-Methyl-3-{[tert-butyl(dimethyl)silyl]oxy}propanoyl and Acetyl Chlorides 碳酸铯促进的2-[（二苯基甲基）氨基]乙酸叔丁基与2-甲基-3-{[叔丁基（二甲基）硅基]氧}丙基和乙酰基氯化物反应的替代途径
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602997
Z. R. Valiullina, G. R. Sunagatullina, M. S. Miftakhov
{"title":"Alternative Pathways in Cesium Carbonate-Promoted Reactions of tert-Butyl 2-[(Diphenylmethylidene)amino]acetate with 2-Methyl-3-{[tert-butyl(dimethyl)silyl]oxy}propanoyl and Acetyl Chlorides","authors":"Z. R. Valiullina,&nbsp;G. R. Sunagatullina,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428025602997","DOIUrl":"10.1134/S1070428025602997","url":null,"abstract":"<p>The reaction of <i>tert</i>-butyl 2-[(diphenylmethylidene)amino]acetate with 2-methyl-3-{[<i>tert</i>-butyl­(dimethyl)silyl]oxy}propanoyl chloride in methylene chloride in the presence of cesium carbonate afforded the corresponding β-lactam and acetylglycine derivative. Acetyl chloride reacted with <i>tert</i>-butyl 2-[(diphenyl­methyli­dene)amino]acetate to produce <i>tert</i>-butyl 2-(acetamido)acetate as the only product with high chemo­selectivity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1384 - 1388"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868943","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
Palladium-Catalyzed Three-Component Coupling of 2-Iodoanilines, Isocyanides, and Carbon Dioxide 钯催化的2-碘苯胺、异氰酸酯和二氧化碳的三组分偶联
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S107042802560305X
T. K. Nguyen, S. A. Katkova, L. A. Kraeva, N. V. Rostovskii, M. A. Kinzhalov
{"title":"Palladium-Catalyzed Three-Component Coupling of 2-Iodoanilines, Isocyanides, and Carbon Dioxide","authors":"T. K. Nguyen,&nbsp;S. A. Katkova,&nbsp;L. A. Kraeva,&nbsp;N. V. Rostovskii,&nbsp;M. A. Kinzhalov","doi":"10.1134/S107042802560305X","DOIUrl":"10.1134/S107042802560305X","url":null,"abstract":"<p>The formation of quinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones via palladium-catalyzed three-component coupling of <i>o</i>-iodoanilines, isocyanides, and carbon dioxide has been studied. The use of the coordinatively unsaturated phosphine complex [PdCl(μ-Cl)(PPh<sub>3</sub>)]<sub>2</sub> in DMF at 80°C under atmospheric CO<sub>2</sub> pressure provided quantitative yield of the target product in 3 h. Optimization of the reaction conditions, including solvent nature, temperature, and reactant ratio has been performed. The molecular mechanism of catalysis involving dynamic equilibrium between the monomeric and dimeric forms of palladium complexes has been proposed on the basis of ESI/HRMS analysis of key intermediates. A broad substrate scope of the reaction, including sterically hindered isocyanides, has been demonstrated. Biological screening of the synthesized quinazolinedione derivatives has shown that some of them exhibit moderate antibacterial activity against methicillin-resistant <i>S. aureus</i>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1319 - 1331"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868857","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
Noncatalytic Synthesis of 5-[4-(Pyrrolidin-1-yl/piperidin-1-yl)­phenyl](bi)pyridines 非催化合成5-[4-（吡咯烷-1-基/吡咯烷-1-基）-苯基]（双）吡啶
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602183
S. E. Vatolina, A. P. Krinochkin, T. A. Tseitler, A. A. Yurtaeva, A. S. Alekseeva, A. S. Markina, V. S. Gaviko, D. S. Kopchuk, G. V. Zyryanov
{"title":"Noncatalytic Synthesis of 5-[4-(Pyrrolidin-1-yl/piperidin-1-yl)­phenyl](bi)pyridines","authors":"S. E. Vatolina,&nbsp;A. P. Krinochkin,&nbsp;T. A. Tseitler,&nbsp;A. A. Yurtaeva,&nbsp;A. S. Alekseeva,&nbsp;A. S. Markina,&nbsp;V. S. Gaviko,&nbsp;D. S. Kopchuk,&nbsp;G. V. Zyryanov","doi":"10.1134/S1070428025602183","DOIUrl":"10.1134/S1070428025602183","url":null,"abstract":"<p>The possibility of noncatalytic substitution of halogen at the <i>para</i>-position of 6-phenyl substituent in 1,2,4-triazines by a cyclic amine (pyrrolidine or piperidine) under solvent-free conditions has been studied. The resulting 1,2,4-triazines can be converted to the corresponding (bi)pyridine derivatives via the Boger reaction with norbornadiene under elevated pressure.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1304 - 1310"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868927","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
Chemoselective Oxidative Cross-Coupling of Secondary Phosphine Chalcogenides with Mercaptoalkanols: Synthesis of S-Hydroxyalkyl Phosphinochalcogenothioates 仲膦硫族化合物与巯基烷醇的化学选择性氧化交偶联：s-羟基烷基膦硫代酸盐的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602638
K. O. Khrapova, P. A. Volkov, A. A. Telezhkin, L. I. Larina
{"title":"Chemoselective Oxidative Cross-Coupling of Secondary Phosphine Chalcogenides with Mercaptoalkanols: Synthesis of S-Hydroxyalkyl Phosphinochalcogenothioates","authors":"K. O. Khrapova,&nbsp;P. A. Volkov,&nbsp;A. A. Telezhkin,&nbsp;L. I. Larina","doi":"10.1134/S1070428025602638","DOIUrl":"10.1134/S1070428025602638","url":null,"abstract":"<p>Oxidative cross-coupling of secondary phosphine chalcogenides with mercaptoalkanols in the presence of CCl<sub>4</sub>/Et<sub>3</sub>N at an equimolar reactant ratio under mild conditions (20–25°C, 2–7 h) afforded the corresponding <i>S</i>-hydroxyalkyl phosphinochalcogenothioates with high chemoselectivity in 76–89% isolated yield.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1273 - 1278"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868593","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
Design, Synthesis, and Biological Evaluation of New Monocarboxylate Transporter MCT1 Inhibitors Based on 1,5-Diarylpyrazoles 新型1,5-二芳基吡唑类单羧酸转运体MCT1抑制剂的设计、合成及生物学评价
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-08-18 DOI: 10.1134/S1070428025602870
I. P. Fonareva, E. E. Kolesnikova, E. V. Mitroshina, E. A. Marasanova, M. V. Vedunova, A. Yu. Fedorov, E. S. Shchegravina
{"title":"Design, Synthesis, and Biological Evaluation of New Monocarboxylate Transporter MCT1 Inhibitors Based on 1,5-Diarylpyrazoles","authors":"I. P. Fonareva,&nbsp;E. E. Kolesnikova,&nbsp;E. V. Mitroshina,&nbsp;E. A. Marasanova,&nbsp;M. V. Vedunova,&nbsp;A. Yu. Fedorov,&nbsp;E. S. Shchegravina","doi":"10.1134/S1070428025602870","DOIUrl":"10.1134/S1070428025602870","url":null,"abstract":"<p>A series of pyrazole derivatives containing an aryl or heteroaryl substituent on C<sup>5</sup> were synthesized according to the proposed scheme which involves Suzuki arylation of pyrazole as the key stage. The synthesized compounds were evaluated as inhibitors of monocarboxylate transporter (MCT) proteins. Compound <b>3a</b> with a chloropyridine substituent on C<sup>5</sup> of the pyrazole ring was found to be the most promising inhibitor of lactate transport into cells. Its activity at concentrations of 25 and 50 μM was comparable with the activity of the approved MCT1 inhibitor BAY-8002 used as reference.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 7","pages":"1259 - 1272"},"PeriodicalIF":0.9,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144868718","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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