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Cp2ZrCl2-Catalyzed 2-Aluminoethylalumination of Aminomethyl Allenes with Triethylaluminum Cp2ZrCl2 与三乙基铝催化的氨甲基烯丙基 2-氨乙基氨化反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120261
T. P. Zosim, R. N. Kadikova, I. R. Ramazanov
{"title":"Cp2ZrCl2-Catalyzed 2-Aluminoethylalumination of Aminomethyl Allenes with Triethylaluminum","authors":"T. P. Zosim,&nbsp;R. N. Kadikova,&nbsp;I. R. Ramazanov","doi":"10.1134/S1070428024120261","DOIUrl":"10.1134/S1070428024120261","url":null,"abstract":"<p>It was shown for the first time that the Cp<sub>2</sub>ZrCl<sub>2</sub>-catalyzed reaction of dialkylaminomethyl allenes (<i>N</i>,<i>N</i>-dialkylbuta-2,3-dien-1-amines) with triethylaluminum results in regio- and stereoselective formation of (<i>Z</i>)-<i>N</i>,<i>N</i>-dialkylhex-2-en-1-amines. A probable reaction mechanism has been proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2508 - 2511"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361994","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
Methyl 5-[Di(1H-pyrrol-2-yl)methyl]-3,4-dimethoxythiophene-2-carboxylate in Approaches to New Thienopyrroles
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120273
S. A. Torosyan, Z. F. Nuriakhmetova, F. A. Gimalova, M. S. Miftakhov
{"title":"Methyl 5-[Di(1H-pyrrol-2-yl)methyl]-3,4-dimethoxythiophene-2-carboxylate in Approaches to New Thienopyrroles","authors":"S. A. Torosyan,&nbsp;Z. F. Nuriakhmetova,&nbsp;F. A. Gimalova,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428024120273","DOIUrl":"10.1134/S1070428024120273","url":null,"abstract":"<p>Selective reduction–oxidation of dimethyl 3,4-dimethoxythiophene-2,5-dicarboxylate gave methyl 5-formyl-3,4-dimethoxythiophene-2-carboxylate and then methyl 5-[di(1<i>H</i>-pyrrol-2-yl)methyl]-3,4-dimethoxy­thiophene-2-carboxylate, and the latter was used to obtain the corresponding BODIPY derivative.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2512 - 2515"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361993","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
Ultrasound-Assisted Cascade Condensation of Isatin, Malononitrile, and β-Keto Esters: An Efficient One-Pot Synthesis of Novel Spirooxindole Derivatives with Expected Anti-Esophageal Cancer Activity 超声辅助伊沙廷、丙二腈和 β-酮酯的级联缩合：具有预期抗食管癌活性的新型螺吲哚衍生物的高效一锅合成方法
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120236
Gh. S. Yaqoob, A. M. Jassem, A. M. Dhumad, H. A. S. Jabir
{"title":"Ultrasound-Assisted Cascade Condensation of Isatin, Malononitrile, and β-Keto Esters: An Efficient One-Pot Synthesis of Novel Spirooxindole Derivatives with Expected Anti-Esophageal Cancer Activity","authors":"Gh. S. Yaqoob,&nbsp;A. M. Jassem,&nbsp;A. M. Dhumad,&nbsp;H. A. S. Jabir","doi":"10.1134/S1070428024120236","DOIUrl":"10.1134/S1070428024120236","url":null,"abstract":"<p>A green and facile one-pot synthesis of novel oxospiro[indole-3,4′-pyran] derivatives via a three-component reaction of isatin, malononitrile, and various β-keto esters in the presence of triethylamine under ultrasonic irradiation is reported. This protocol offers several ecological benefits including simple methodology, good to excellent yields, clean reaction, higher atom economy, shorter reaction time, and environmental friendliness. Molecular docking of the synthesized spirooxindole derivatives was performed to evaluate their anti-esophageal cancer activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2483 - 2494"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362047","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 4-Aroyl-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-5-(metoxycarbonyl)-1H-pyrrol-2,3-diones with 4-Aminoazobenzene
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110198
V. A. Lyadov, D. E. Makrushin, E. S. Denislamova, A. N. Maslivets
{"title":"Reaction of 4-Aroyl-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-5-(metoxycarbonyl)-1H-pyrrol-2,3-diones with 4-Aminoazobenzene","authors":"V. A. Lyadov,&nbsp;D. E. Makrushin,&nbsp;E. S. Denislamova,&nbsp;A. N. Maslivets","doi":"10.1134/S1070428024110198","DOIUrl":"10.1134/S1070428024110198","url":null,"abstract":"<p>The reactions of 4-aroyl-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)-5-(methoxycarbonyl)-1<i>H</i>-pyrrole-2,3-diones with <i>p</i>-aminoazobenzene leads to the formation of methyl 3-aroyl-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)-4-hydroxy-5-oxo-2-[4-(phenyldiazenyl)benzyl]-2,5-dihydro-1<i>H</i>-pyrrole-2-carboxylates.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2302 - 2304"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109432","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 Pyrrole, Pyrazole, Triazole, Thiazole, Thiadiazole, and Pyrazine Derivatives from Hydrazonoyl Halides (A Review)
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110125
E. S. Alwan
{"title":"Synthesis of Pyrrole, Pyrazole, Triazole, Thiazole, Thiadiazole, and Pyrazine Derivatives from Hydrazonoyl Halides (A Review)","authors":"E. S. Alwan","doi":"10.1134/S1070428024110125","DOIUrl":"10.1134/S1070428024110125","url":null,"abstract":"<p>A review of the synthesis of pyrrole, pyrazole, triazole, thiadiazole, and pyrazine derivatives from hydrazonoyl halides is presented. These heterocyclic compounds are a very important class in medicinal chemistry due to their antimicrobial, tuberculostatic, anticancer, antifungal, and other biological activities. Hydrazonoyl halides are an essential source of 1,3-dipolar reagents in alkaline media, which react with alkenes to give five-member rings.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2228 - 2241"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109286","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
Study of the Mechanism of the Alkylation of 2-Methylimidazole with 1,1,3,3-Tetraiodopropane-2-one by MALDI Mass Spectrometry
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110083
L. V. Klyba, E. R. Sanzheeva, I. A. Dorofeev, V. A. Shagun, G. A. Fedorova
{"title":"Study of the Mechanism of the Alkylation of 2-Methylimidazole with 1,1,3,3-Tetraiodopropane-2-one by MALDI Mass Spectrometry","authors":"L. V. Klyba,&nbsp;E. R. Sanzheeva,&nbsp;I. A. Dorofeev,&nbsp;V. A. Shagun,&nbsp;G. A. Fedorova","doi":"10.1134/S1070428024110083","DOIUrl":"10.1134/S1070428024110083","url":null,"abstract":"<p>The mechanism of the alkylation of 2-methylimidazole with 1,1,3,3-tetraiodopropan-2-one in the absence and presence of HI acceptor (CaCO<sub>3</sub>) by matrix-assisted laser desorption/ionization mass spectrometry was studied for the first time. The composition of the reaction mixtures and possible routes of the formation of functionalized 2-methylimidazole derivatives were determined. The N<sup>1</sup> and N<sup>1,3</sup>-alkylation of 2-methylimidazole with reduced (1-iodopropan-2-one, 1,3-diiodopropan-2-one) or dehydroiodinated (2,3-diiodo-2-cycloprop-1-ene) gives rise to forms 1,1, 3,3-tetraiodopropan-2-one is a key step in the synthesis. The thermodynamic and kinetic characteristics of the reduction and dehydroiodination of 1,1,3,3-tetraiodoacetone were evaluated by B3LYP/6-311+G(d,p)+dgdzvp) quantum-chemical calculations.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2147 - 2156"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109296","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 (Carboxymethylidene)cyclopentenedione Derivatives via the Oxidative Cleavage of the Allylic Double Bond in 2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110186
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov
{"title":"Synthesis of (Carboxymethylidene)cyclopentenedione Derivatives via the Oxidative Cleavage of the Allylic Double Bond in 2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione","authors":"V. A. Egorov,&nbsp;L. S. Khasanova,&nbsp;F. A. Gimalova,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428024110186","DOIUrl":"10.1134/S1070428024110186","url":null,"abstract":"<p>The oxidative cleavage reactions of the allylic double bond in 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione in the OsO<sub>4</sub>–NaIO<sub>4</sub> and KMnO<sub>4</sub>–Et<sub>3</sub>BnN<sup>+</sup>Cl<sup>–</sup> systems were studied. The periodate cleavage of the starting 2-allylcyclopentene-1,3-dione gave an aldehyde, whose oxidation with the Jones reagent followed by HCl elimination resulted in the formation of the target 2-(carboxymethylidene)cyclopent-4-ene-1,3-dione. In the alternative approach, the permanganate oxidation of the starting 2-allylcyclopentene-1,3-dione led to the corresponding diol in a moderate yield.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2298 - 2301"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109679","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 and Analgesic Activity of Substituted N-Alkyl-4-aryl-2-aroylhydrazylidene-4-oxobutanamides
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110101
E. I. Denisova, O. V. Zvereva, D. V. Lipin, R. R. Makhmudov, I. N. Chernov, E. S. Denislamova, D. A. Shipilovskikh, N. M. Igidov
{"title":"Synthesis and Analgesic Activity of Substituted N-Alkyl-4-aryl-2-aroylhydrazylidene-4-oxobutanamides","authors":"E. I. Denisova,&nbsp;O. V. Zvereva,&nbsp;D. V. Lipin,&nbsp;R. R. Makhmudov,&nbsp;I. N. Chernov,&nbsp;E. S. Denislamova,&nbsp;D. A. Shipilovskikh,&nbsp;N. M. Igidov","doi":"10.1134/S1070428024110101","DOIUrl":"10.1134/S1070428024110101","url":null,"abstract":"<p>A series of new substituted derivatives of <i>N</i>-alkyl-4-aryl-2-aroylhydrazylidene-4-oxobutanamides were synthesized via the opening of the furan ring in substituted 3-<i>N</i>-5-aryl-2-oxofuran-3(2<i>H</i>)-ylidene-4-R<sup>1</sup>-benzohydrazides under the action of various alkylamines. The in vivo analgesic activity and acute toxicity of the synthesized compounds were assessed to show that they have a pronounced analgesic activity and are almost nontoxic.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2162 - 2169"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109288","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
Ruthenium-catalyzed C3 Alkylation of the Furan/Thiophene Ring in 2-(Furan-2-carbonyl)/(Thiophene-2-carbonyl)-1-methylimidazoles with Acrylic Acid Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110071
K. E. Shepelenko, I. G. Gnatiuk, V. M. Chernyshev
{"title":"Ruthenium-catalyzed C3 Alkylation of the Furan/Thiophene Ring in 2-(Furan-2-carbonyl)/(Thiophene-2-carbonyl)-1-methylimidazoles with Acrylic Acid Derivatives","authors":"K. E. Shepelenko,&nbsp;I. G. Gnatiuk,&nbsp;V. M. Chernyshev","doi":"10.1134/S1070428024110071","DOIUrl":"10.1134/S1070428024110071","url":null,"abstract":"<p>A method for the synthesis of 3-alkyl-2-(furan-2-carbonyl)/(thiophene-2-carbonyl)-1-methylimidazoles by the ruthenium-catalyzed selective C<sup>3</sup> alkylation of the furan or thiophene ring in 2-(furan-2-carbonyl)/(thiophene-2-carbonyl)-1-methylimidazoles with acrylic acid esters, amides, or nitrile has been developed. The resulting compounds may be of interest as polyfunctional reagents for preparing 3-(2-carboxyethyl)furan/thiophene-2-carboxylic acid derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2140 - 2146"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109294","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
Substituted-1,3,4-oxadiazole Indole Derivatives: Design, Synthesis, Characterization, and Evaluation of the Antimicrobial and Anti-Inflammatory Activities
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110162
Medarametla Venkatesh, Chappidi Hazarathaiah Yadav, Mavallur Varalakshmi
{"title":"Substituted-1,3,4-oxadiazole Indole Derivatives: Design, Synthesis, Characterization, and Evaluation of the Antimicrobial and Anti-Inflammatory Activities","authors":"Medarametla Venkatesh,&nbsp;Chappidi Hazarathaiah Yadav,&nbsp;Mavallur Varalakshmi","doi":"10.1134/S1070428024110162","DOIUrl":"10.1134/S1070428024110162","url":null,"abstract":"<p>In view of the significant biological potency of indole derivatives and 1,3,4-oxadiazoles, in the present work we synthesized a new series of indole-based substituted 1,3,4-oxadiazole derivatives, specifically 1-[5-(1<i>H</i>-indol-5-yl)-2-substituted-1,3,4-oxadiazol-3(2<i>H</i>)-yl]ethenones from 1<i>H</i>-indole-5-carboxylic acid through a sequence of reactions. All the synthesized compounds were evaluated for their antimicrobial and ant-inflammatory activities. The results of the antimicrobial assay showed that most of the products exhibited promising activity against the tested bacterial strains, especially <i>P. aeruginosa</i> (ATCC27853) with MIC 6.25 μg/mL, whereas very few compounds showed a high antifungal activity with MICs ranging from 6.25 to 50.0 μg/mL. All the synthesized compounds showed a low to moderate antiinflammatory activity with the albumin denaturation inhibition activity of &lt; 66%, which is lower than that of the standard drug diclofenac (85.5%). Overall, the biological testing showed that the indole-based substituted 1,3,4-oxadiazole derivatives act as potent antibacterial rather than anti-inflammatory agents, and their activity can be enhanced by the introduction of an appropriate pharmacophoric substituent in the 1,3,4-oxadiazole motif.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2276 - 2289"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109414","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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