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Russian Journal of Organic Chemistry最新文献

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Green and Efficient Synthesis of 1H-Pyrazole-Conjugated 5,6,7,9-Tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-ones 1h -吡唑偶联5,6,7,9-四氢四唑[5,1-b]喹唑啉-8(4H)-酮的绿色高效合成
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024603571
K. Kalpana
{"title":"Green and Efficient Synthesis of 1H-Pyrazole-Conjugated 5,6,7,9-Tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-ones","authors":"K. Kalpana","doi":"10.1134/S1070428024603571","DOIUrl":"10.1134/S1070428024603571","url":null,"abstract":"<p>1<i>H</i>-Pyrazole-conjugated tetrazoloquinazolinone scaffolds represent crucial structural motifs in various novel chemical entities with medicinal potential. 9-(1<i>H</i>-pyrazol-5-yl)-5,6,7,9-tetrahydrotetrazolo­[5,1-<i>b</i>]­quinazolin-8(4<i>H</i>)-one derivatives were efficiently synthesized in 85–90% yields by the reaction of methyl- and dimethyl-substituted 1<i>H</i>-pyrazole-5-carbaldehydes, 1<i>H</i>-tetrazol-5-amine, and dimedone or cyclo­hexane-1,3-dione using the ionic liquid [BMIM][OH] as a green reaction medium at 75–80°C for 40–60 min. The synthesized compounds were characterized by NMR and mass spectra. This synthetic methodology offers several advantages, including high yields, a straightforward protocol, environmental compatibility, short reaction times, and mild reaction conditions. Notably, the use of a catalytically active ionic liquid as reaction medium obviates the necessity for additional catalysts and solvents, thus streamlining the synthetic process and aligning with principles of green chemistry. Overall, this approach holds promise for the efficient and sustainable synthesis of 1<i>H</i>-pyrazole-conjugated tetrazoloquinazolinone derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"499 - 503"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919124","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
Efficient Synthesis and Biological Evaluation of 1,4-Disubstituted 3-Cyanopyridin-2(1H)-ones as Selective Inhibitors of the Post-Acid Activity of Mammalian 20S Proteasomes 1,4-二取代3-氰吡啶-2(1H)- 1作为哺乳动物20S蛋白酶体酸后活性选择性抑制剂的高效合成及生物学评价
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S107042802460373X
L. V. Karapetyan, G. G. Tokmajyan, G. S. Melikyan, M. Bouvier-Durand, M. Reboud-Ravaux, T. H. Pham
{"title":"Efficient Synthesis and Biological Evaluation of 1,4-Disubstituted 3-Cyanopyridin-2(1H)-ones as Selective Inhibitors of the Post-Acid Activity of Mammalian 20S Proteasomes","authors":"L. V. Karapetyan,&nbsp;G. G. Tokmajyan,&nbsp;G. S. Melikyan,&nbsp;M. Bouvier-Durand,&nbsp;M. Reboud-Ravaux,&nbsp;T. H. Pham","doi":"10.1134/S107042802460373X","DOIUrl":"10.1134/S107042802460373X","url":null,"abstract":"<p>A set of new 1,4-disubstituted 3-cyanopyridin-2(1<i>H</i>)-ones were synthesized in good yields by a simple and handy method using various primary amines for the construction of pyridine ring. The synthesized compounds were tested on three types of catalytic sites of mammalian constitutive 20S proteasome (c20S) and 20S immunoproteasome (i20S). Most of the new compounds (<b>7a</b>–<b>7g</b>) specifically inhibited the post-acid (PA) activity in the low micromolar range. Compounds <b>7h</b> and <b>7i</b> poorly inhibited the three types of catalytic activities. Challenging proteases calpain I and cathepsin B were not inhibited.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"449 - 455"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143918930","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
Catalytic Oxidation of Organic Molecules by Cold Plasma in the Presence of Magnetic Iron Compounds 磁性铁化合物存在下冷等离子体对有机分子的催化氧化
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024603716
H. Hassani, A. Raghavi, A. Abbaszadeh
{"title":"Catalytic Oxidation of Organic Molecules by Cold Plasma in the Presence of Magnetic Iron Compounds","authors":"H. Hassani,&nbsp;A. Raghavi,&nbsp;A. Abbaszadeh","doi":"10.1134/S1070428024603716","DOIUrl":"10.1134/S1070428024603716","url":null,"abstract":"<p>Aldehydes and ketones play a crucial role as intermediates in forming C–C bonds and are present in various target molecules like pharmaceuticals and natural compounds. This study presents an effective catalytic method for producing aldehydes and ketones in the presence of cold plasma using Fe<sub>3</sub>O<sub>4</sub>@CeO<sub>2</sub> magnetic nanoparticles as a catalyst. No need for oxidants and solvents along with a significant reduction in oxidation time are the advantages of this method compared to previous methods. Furthermore, the catalyst can be reused in up to four consecutive reactions without significant loss of activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"492 - 498"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919092","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 Facile Environment-Friendly Synthesis of 7-(Naphthalen-1-yl)­pyrazolo[1,5-a]pyrimidine Analogues via Aza-Michael Addition–Elimination–Cyclodehydration. X-Ray Crystallography and Structural Elucidation Aza-Michael加成-消除-环脱水法合成7-（萘-1-酰基）-吡唑[1,5- A]嘧啶类似物x射线晶体学和结构解析
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024604059
T. R. A. Sangma, D. K. Lamin, T. S. Sangma, C. R. Marak, L. B. Marpna, S. Kaping, J. N. Vishwakarma
{"title":"A Facile Environment-Friendly Synthesis of 7-(Naphthalen-1-yl)­pyrazolo[1,5-a]pyrimidine Analogues via Aza-Michael Addition–Elimination–Cyclodehydration. X-Ray Crystallography and Structural Elucidation","authors":"T. R. A. Sangma,&nbsp;D. K. Lamin,&nbsp;T. S. Sangma,&nbsp;C. R. Marak,&nbsp;L. B. Marpna,&nbsp;S. Kaping,&nbsp;J. N. Vishwakarma","doi":"10.1134/S1070428024604059","DOIUrl":"10.1134/S1070428024604059","url":null,"abstract":"<p>The functionalization of 1-acetylnaphthalene (<b>1</b>) through the reaction with dimethylformamide dimethyl acetal resulted in the formation of 3-(dimethylamino)-1-(naphthalen-1-yl)prop-2-en-1-one (<b>2</b>) which reacted with substituted aminopyrazoles <b>3</b> in the presence of KHSO<sub>4</sub> in aqueous media under ultrasonic irradiation, yielding novel substituted 7-(naphthalen-1-yl)pyrazolo[1,5-<i>a</i>]pyrimidine derivatives <b>4a</b> and <b>4b</b>. The structures of these compounds were confirmed by analytical and spectral data, as well as by X-ray crys­tallo­graphic analysis of compound <b>4b</b>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"511 - 517"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919110","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 Chemical Properties of (E)-3-[3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]propenoic Acid Derivatives (E)-3-[3-（2,5-二氧基-2,5-二氢- 1h -吡咯-1-基）苯基]丙烯酸衍生物的合成及化学性质
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S107042802460462X
O. A. Kolyamshin, Yu. N. Mitrasov, V. A. Danilov, A. A. Avruyskaya, Yu. Yu. Pylchikova
{"title":"Synthesis and Chemical Properties of (E)-3-[3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]propenoic Acid Derivatives","authors":"O. A. Kolyamshin,&nbsp;Yu. N. Mitrasov,&nbsp;V. A. Danilov,&nbsp;A. A. Avruyskaya,&nbsp;Yu. Yu. Pylchikova","doi":"10.1134/S107042802460462X","DOIUrl":"10.1134/S107042802460462X","url":null,"abstract":"<p>The reaction of <i>m</i>-aminocinnamic acid with maleic anhydride in acetone gave (2<i>Z</i>)-4-{3-[(<i>E</i>)-2-carboxyethenyl]anilino}-4-oxobut-2-enoic acid which underwent intramolecular cyclization in the presence of <i>p</i>-toluenesulfonic acid to produce (<i>E</i>)-3-[3-(2,5-dioxo-2,5-dihydro-1<i>H</i>-pyrrol-1-yl)phenyl]prop-2-enoic acid. <i>m</i>-Aminocinnamic acid potassium salts reacted with 2-(bromomethyl)-1,1-dichlorocyclopropane with retention of the three-membered ring, chemoselectively yielding 2,2-dichlorocyclopropylmethyl (2<i>E</i>)-3-(3-aminophenyl)­prop-2-enoate. Successive reactions of the latter with maleic anhydride and with acetic anhydride in the presence of sodium acetate afforded 2,2-dichlorocyclopropylmethyl (2<i>E</i>)-3-[3-(2,5-dioxo-2,5-dihydro-1<i>H</i>-pyrrol-1-yl)phenyl]prop-2-enoate which was subjected to aza-Michael reaction with secondary amines to obtain 2,2-dichlorocyclopropylmethyl (<i>E</i>)-3-[3-(3-dialkylamino-2,5-dioxopyrrolidin-1-yl)phenyl]prop-2-enoates.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"385 - 391"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919219","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
Method of Regeneration of DMSO-d6 DMSO-d6的再生方法
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024604539
D. A. Lomov
{"title":"Method of Regeneration of DMSO-d6","authors":"D. A. Lomov","doi":"10.1134/S1070428024604539","DOIUrl":"10.1134/S1070428024604539","url":null,"abstract":"<p>A method has been proposed for the regeneration of DMSO-<i>d</i><sub>6</sub> by azeotropic distillation of water and volatile impurities with carbon tetrachloride, followed by removal of impurities distillable with DMSO-<i>d</i><sub>6</sub> through complexation with copper ions.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"548 - 550"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919264","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
Cyclization of Ethyl 2-[Cyano(4,6-dimethylpyrimidin-2-yl)amino]acetate 2-[氰基（4,6-二甲基嘧啶-2-基）氨基]乙酸乙酯的环化
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024604667
A. K. Shiryaev, M. S. Krasavina, V. A. Shiryaev
{"title":"Cyclization of Ethyl 2-[Cyano(4,6-dimethylpyrimidin-2-yl)amino]acetate","authors":"A. K. Shiryaev,&nbsp;M. S. Krasavina,&nbsp;V. A. Shiryaev","doi":"10.1134/S1070428024604667","DOIUrl":"10.1134/S1070428024604667","url":null,"abstract":"<p>Ethyl 2-[cyano(4,6-dimethylpyrimidin-2-yl)amino]acetate reacted with morpholine, piperidine, and acid hydrazides to give the corresponding imidazolin-4-one derivatives. Cyclization of the title compound in the presence of sulfuric acid afforded 2-iminooxazolin-5-one derivative. The latter rearranged into imidazolidine-2,4-dione by the action of potassium cyanate, and its acylation involved the imino nitrogen atom.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"428 - 434"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919097","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
CBr4-Mediated Oxidative Desulfurization of N,N′-Disubstituted Thioureas: An Expedient Route to 5-Aminotetrazoles cbr4介导的N，N ' -二取代硫脲氧化脱硫：制备5-氨基四唑的便捷途径
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428023600201
B. Yadav,  Pragati, K. Lal, R. Kumar, Y. Singh, S. Das, A. K. Shukla, A. Yadav, S. K. Srivastava
{"title":"CBr4-Mediated Oxidative Desulfurization of N,N′-Disubstituted Thioureas: An Expedient Route to 5-Aminotetrazoles","authors":"B. Yadav,&nbsp; Pragati,&nbsp;K. Lal,&nbsp;R. Kumar,&nbsp;Y. Singh,&nbsp;S. Das,&nbsp;A. K. Shukla,&nbsp;A. Yadav,&nbsp;S. K. Srivastava","doi":"10.1134/S1070428023600201","DOIUrl":"10.1134/S1070428023600201","url":null,"abstract":"<p>A highly efficient environmentally friendly synthetic method was developed to synthesize 5-amino­tetrazole derivatives through oxidative desulfurization of <i>N</i>,<i>N</i>′-disubstituted thiourea with sodium azide using carbon tetrabromide as a thiophilic reagent. The proposed protocol also offers a unique and convenient method for synthesizing 5-amino tetrazoles at room temperature without using any expensive reagent or toxic heavy metal salts by employing readily available, cheap, inexpensive, odorless, and easily handled bromine sources. The developed methodology involves very modest reaction conditions and affords easily isolable products with excellent yield.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"518 - 526"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919111","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 a Hexasubstituted Benzene Derivative from Pyridine-4-carbaldehyde and Malononitrile 吡啶-4-乙醛与丙二腈合成六取代苯衍生物
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024604473
I. G. Mamedov, F. N. Naghiyev, I. A. Yakushev, V. N. Khrustalev
{"title":"Synthesis of a Hexasubstituted Benzene Derivative from Pyridine-4-carbaldehyde and Malononitrile","authors":"I. G. Mamedov,&nbsp;F. N. Naghiyev,&nbsp;I. A. Yakushev,&nbsp;V. N. Khrustalev","doi":"10.1134/S1070428024604473","DOIUrl":"10.1134/S1070428024604473","url":null,"abstract":"<p>Previously unknown 2-amino-4,6-di(pyridin-4-yl)benzene-1.3.5-tricarbonitrile has been synthesized by the 2:1 condensation of 2-(pyridin-4-ylmethylidene)malononitrile with malononitrile in the presence of <i>N</i>-methylpiperazine as catalyst. The product structure has been determined by NMR spectroscopy and X-ray analysis, and a probable mechanism of its formation has been proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"554 - 557"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919091","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
L-Proline as a Catalyst for the Synthesis of Polysubstituted Pyran Derivatives via Multicomponent Reaction l -脯氨酸在多组分反应合成多取代吡喃衍生物中的催化作用
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-05-07 DOI: 10.1134/S1070428024603364
Mugada Sugunakara Rao, M. Ravi Chandra, T. V. S. P. V. Satya Guru
{"title":"L-Proline as a Catalyst for the Synthesis of Polysubstituted Pyran Derivatives via Multicomponent Reaction","authors":"Mugada Sugunakara Rao,&nbsp;M. Ravi Chandra,&nbsp;T. V. S. P. V. Satya Guru","doi":"10.1134/S1070428024603364","DOIUrl":"10.1134/S1070428024603364","url":null,"abstract":"<p>An operationally simple, one-pot multicomponent protocol has been developed for the assembly of polysubstituted pyrans via an atom-economic transformation incorporating benzaldehyde, 4-hydroxycoumarin (dimedone, or cyclohexane-1,3-dione), and benzoylacetonitriles. This process involves L-proline-catalyzed domino condensation and Michael addition. The reaction is carried out by simply mixing the reactants and the catalyst in ethanol, followed by heating at 70°C, and the products are isolated in good yields after convenient workup.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"475 - 483"},"PeriodicalIF":0.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919105","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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