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Synthesis of 4-Substituted 3-Nitrophenyl Carbonyl Compounds from Benzyl Alcohols
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120054
D. A. Kazantsev, A. A. Denisov, A. V. Pestov
{"title":"Synthesis of 4-Substituted 3-Nitrophenyl Carbonyl Compounds from Benzyl Alcohols","authors":"D. A. Kazantsev,&nbsp;A. A. Denisov,&nbsp;A. V. Pestov","doi":"10.1134/S1070428024120054","DOIUrl":"10.1134/S1070428024120054","url":null,"abstract":"<p>A procedure has been developed for the synthesis of 4-R-3-nitrophenyl carbonyl compounds via tandem oxidation–nitration of benzyl alcohols. The proposed one-pot procedure makes it possible to obtain the target products in good yields under mild conditions using stable commercially available reagents. The major requirement to the substrate structure is the presence of a mesomeric donor substituent at the <i>para</i> position with respect to the hydroxymethyl group.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2345 - 2350"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024120054.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361918","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Evaluation of Neurotropic Activity of New Terahydropyridazin-3-one Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120030
R. Dzh. Khachikyan, Z. G. Hovakimyan, H. A. Panosyan, L. S. Mirzoyan, R. G. Paronikyan
{"title":"Synthesis and Evaluation of Neurotropic Activity of New Terahydropyridazin-3-one Derivatives","authors":"R. Dzh. Khachikyan,&nbsp;Z. G. Hovakimyan,&nbsp;H. A. Panosyan,&nbsp;L. S. Mirzoyan,&nbsp;R. G. Paronikyan","doi":"10.1134/S1070428024120030","DOIUrl":"10.1134/S1070428024120030","url":null,"abstract":"<p>4-Aryl-4-oxo-2-(1,2-substituted 1<i>H</i>-indol-3-yl)butanoic acids reacted with hydrazine to give 6-aryl-4-(1,2-substituted 1<i>H</i>-indol-3-yl)-2,3,4,5-tetrahydropyridazin-3-ones, whereas heterocyclization of structurally related 4-aryl-4-oxo-2-hetarylbutanoic acids under similar conditions was accompanied by elimination of the azole moiety, leading to the formation of 6-aryl-2,3-dihydropyridazin-3-ones. Study of neurotropic activity of the new tetrahydropyridazinone derivatives revealed anxiolytic effect of all compounds.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2331 - 2335"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361920","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, Characterization, and Biological Activity of 1-(Pyridin-4-yl)-1H-pyrazol-5-amine Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120157
P. A. Rechel, S. Jyothi
{"title":"Synthesis, Characterization, and Biological Activity of 1-(Pyridin-4-yl)-1H-pyrazol-5-amine Derivatives","authors":"P. A. Rechel,&nbsp;S. Jyothi","doi":"10.1134/S1070428024120157","DOIUrl":"10.1134/S1070428024120157","url":null,"abstract":"<p>2-Chloro-<i>N</i>-[3-methyl-1-(pyridin-4-yl)-1<i>H</i>-pyrazol-5-yl]acetamide (<b>2</b>) was synthesized from 3-methyl-1-(pyridin-4-yl)-1<i>H</i>-pyrazol-5-amine (<b>1</b>) and chloroacetyl chloride in DMF under reflux condition in a straightforward and very efficient process. New pyrazole derivatives were synthesized from compounds <b>1</b> and <b>2</b> and were characterized by elemental analysis, IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and mass spectroscopy. The anti­microbial activity of the synthesized compounds was evaluated against a variety of bacterial and fungal species in comparison to streptomycin and nystatin, respectively.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2417 - 2421"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361998","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
Microwave Activation of the [FeCl3·6H2O–TsOH·H2O]-Catalyzed Reaction of Norbornene with Organic Nitriles
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S107042802412008X
K. S. Frolova, T. P. Zosim, I. R. Ramazanov
{"title":"Microwave Activation of the [FeCl3·6H2O–TsOH·H2O]-Catalyzed Reaction of Norbornene with Organic Nitriles","authors":"K. S. Frolova,&nbsp;T. P. Zosim,&nbsp;I. R. Ramazanov","doi":"10.1134/S107042802412008X","DOIUrl":"10.1134/S107042802412008X","url":null,"abstract":"<p>An efficient catalytic system consisting of 20 mol % FeCl<sub>3</sub>·6H<sub>2</sub>O and 20 mol % of <i>p</i>-toluenesulfonic acid has been proposed for the amidation of norbornene in toluene with organic nitriles under microwave irradiation at 95°C for 1 h. The corresponding <i>N</i>-(norbornan-2-<i>exo</i>-yl) carboxamides have been obtained with high yields. The efficiency of InCl<sub>3</sub> in the amidation of norbornene with aryl cyanides has been demonstrated for the first time.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2362 - 2366"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S107042802412008X.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362011","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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
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
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
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
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