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Helical Poly(phenyl isocyanide)-Supported (R,R)-(–)-1,2-Diaminocyclohexane Catalyst for Direct Asymmetric Aldol Reaction
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428025020198
Chonglong Li, Caiyun Lai, Murong Zhan, Xiaona Zhao, Wenyuan Dong, Jiaqi Liu, Peibiao Wang
{"title":"Helical Poly(phenyl isocyanide)-Supported (R,R)-(–)-1,2-Diaminocyclohexane Catalyst for Direct Asymmetric Aldol Reaction","authors":"Chonglong Li,&nbsp;Caiyun Lai,&nbsp;Murong Zhan,&nbsp;Xiaona Zhao,&nbsp;Wenyuan Dong,&nbsp;Jiaqi Liu,&nbsp;Peibiao Wang","doi":"10.1134/S1070428025020198","DOIUrl":"10.1134/S1070428025020198","url":null,"abstract":"<p>A novel helical poly(phenyl isocyanide) bearing an (<i>R,R</i>)-(‒)-1,2-diaminocyclohexane pendant (poly-<b>2</b><sub>200</sub>) was designed and synthesized. Helical poly-<b>2</b><sub>200</sub> showed an excellent catalytic performance in the asymmetric aldol reaction between cyclohexanone and 2-(trifluoromethyl)benzaldehyde in ethanol: the reaction product had an enantiomeric excess (<i>ee</i>) of 87.8%.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"338 - 345"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830815","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
Tetrabutylammonium Iodide-Catalyzed Oxidative Coupling of Enol Acetates with Sodium Sulfinates: A Mild Access to β-Keto Sulfones
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428025020174
Babita Yadav
{"title":"Tetrabutylammonium Iodide-Catalyzed Oxidative Coupling of Enol Acetates with Sodium Sulfinates: A Mild Access to β-Keto Sulfones","authors":"Babita Yadav","doi":"10.1134/S1070428025020174","DOIUrl":"10.1134/S1070428025020174","url":null,"abstract":"<p>An efficient, one-pot, and metal-free catalytic synthesis of β-keto sulfones was developed through the oxidative sulfonylation of enol acetates with readily available sodium sulfinates. The protocol involves tetrabutylammonium iodide (TBAI) as a catalyst and <i>tert</i>-butyl hydroperoxide (TBHP) as an oxidant at 60°C. The developed protocol offers such advantages as the use of commercially available inexpensive catalysts and oxidants and safe and environmentally benign conditions, and it provides a facile and mild access to a variety of β-keto sulfones.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"320 - 329"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830892","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-Disubstituted-3-thioindoles by the Madelung Reaction
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428025600779
G. K. Sterligov, M. A. Rasskazova, M. A. Topchiy, A. F. Asachenko
{"title":"Synthesis of 1,2-Disubstituted-3-thioindoles by the Madelung Reaction","authors":"G. K. Sterligov,&nbsp;M. A. Rasskazova,&nbsp;M. A. Topchiy,&nbsp;A. F. Asachenko","doi":"10.1134/S1070428025600779","DOIUrl":"10.1134/S1070428025600779","url":null,"abstract":"<p>1,2-Disubstituted-3-thioindoles were synthesized by the Madelung reaction from the available starting compounds benzyl sulfides. The synthesis under the optimized conditions (0.2 M benzyl sulfide in THF, 2 equiv LDA) gave 1,2-disubstituted-3-thioindoles with electron-donor and electron-acceptor substituents in the 5 and 6 positions, as well as with aromatic and aliphatic substituents on the sulfur atom in high yields (62–93%).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"217 - 224"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830789","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
An Expeditious Solid-Phase Synthesis of 2-Aryl-cyclohepta[b]pyran-4,9-diones under Solvent-Free Conditions
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428025020204
D. Kumar
{"title":"An Expeditious Solid-Phase Synthesis of 2-Aryl-cyclohepta[b]pyran-4,9-diones under Solvent-Free Conditions","authors":"D. Kumar","doi":"10.1134/S1070428025020204","DOIUrl":"10.1134/S1070428025020204","url":null,"abstract":"<p>An expeditious and ecofriendly synthesis of 2-arylcyclohepta[<i>b</i>]pyran-4,9-diones involving oxidative cyclization of 2-hydroxy-3-(3-arylacryloyl)cyclohepta-2,4,6-trienones with silica-supported iodine under grinding conditions has been developed. The procedure offers the follwing advantages: the synthesis occurs under solvent-free conditions at room temperature and it provides high yields of the target products in shorter reaction times and involves no hazardous chemicals and organic solvents at any stage.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"346 - 351"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830888","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, Identification, and Antioxidant Activity Evaluation of New Diazine 2-Sulfanylbenzoxadiazole Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S107042802460150X
S. J. Abed, M. R. Ahmad
{"title":"Synthesis, Identification, and Antioxidant Activity Evaluation of New Diazine 2-Sulfanylbenzoxadiazole Derivatives","authors":"S. J. Abed,&nbsp;M. R. Ahmad","doi":"10.1134/S107042802460150X","DOIUrl":"10.1134/S107042802460150X","url":null,"abstract":"<p>Previously unknown 1-(2-{[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetyl)tetrahydropyridazine-3,6-dione, 1-(2-{[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetyl)tetrahydropyridazine-1,4-dione, and 2-(2-{[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetyl)-2,3,5,6,7,8-hexahydrophthalazine-1,4-dione were synthesized by the reaction of 2-{[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetohydrazide with succinic, phthalic, and 3,4,5,6-tetrahydrophthalic anhydrides, respectively, in glacial acetic acid. The synthesized compounds were characterized by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, and their potency as antioxidants was evaluated. 1-(2-{[5-(2-Hydroxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetyl)tetrahydropyridazine-3,6-dione showed a higher antioxidant activity than the reference antioxidants ascorbic acid that BHT.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"288 - 291"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830787","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 (3aS,4S,6aR)-2-Oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-yl Acetate as a Key Synthon for (–)-Galiellalactone
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428024603479
A. M. Gimazetdinov, V. V. Zagitov, Z. R. Makaev, M. S. Miftakhov
{"title":"Synthesis of (3aS,4S,6aR)-2-Oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-yl Acetate as a Key Synthon for (–)-Galiellalactone","authors":"A. M. Gimazetdinov,&nbsp;V. V. Zagitov,&nbsp;Z. R. Makaev,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428024603479","DOIUrl":"10.1134/S1070428024603479","url":null,"abstract":"<p>The synthesis of a bicyclic allyl acetate, a promising precursor of (–)-galiellalactone, is performed. The synthetic approach is based on separation of the diastereomeric carboxamides prepared by the amidation of racemic <i>gem</i>-dichloro-substituted Grieco lactone with (+)-α-methylbenzylamine. The subsequent steps of transformation of an individual diastereomer involve complete reductive dechlorination, construction of an allyl alcohol fragment in the ring part by stereo- and regiospecific bromohydroxylation with NBS in aqueous THF, and dehydrobromination.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"253 - 257"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830794","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 New Class of Functionalized Isoxazole/Isoxazoline Styrylchromone Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428025020162
P. Limbadri, Y. Hemasri
{"title":"Synthesis of a New Class of Functionalized Isoxazole/Isoxazoline Styrylchromone Derivatives","authors":"P. Limbadri,&nbsp;Y. Hemasri","doi":"10.1134/S1070428025020162","DOIUrl":"10.1134/S1070428025020162","url":null,"abstract":"<p>A simple and practical method of synthesis of a new series of functionalized isoxazole/isoxazoline styrylchromone derivatives from 3-hydroxy-2-styrylchromone <i>via</i> an alkene/alkyne-tethered intermediate by adopting intermolecular 1,3-dipolar cycloaddition of nitrile oxide in the presence of the environmentally safe sodium hypochloride oxidant under mild reaction conditions. The structures of all the synthesized compounds were confirmed by <sup>1</sup>H and <sup>13</sup>C NMR, ESI–MS, and ESI-HRMS.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"312 - 319"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830891","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 [(E)-3-Aryl-3-oxoprop-1-en-1-yl]triphenylphosphonium Bromides with 2-Aminopyridine
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428024603522
R. J. Khachikyan, K. K. Harutyunyan, A. G. Ayvazyan, Z. G. Hovakimyan
{"title":"Reaction of [(E)-3-Aryl-3-oxoprop-1-en-1-yl]triphenylphosphonium Bromides with 2-Aminopyridine","authors":"R. J. Khachikyan,&nbsp;K. K. Harutyunyan,&nbsp;A. G. Ayvazyan,&nbsp;Z. G. Hovakimyan","doi":"10.1134/S1070428024603522","DOIUrl":"10.1134/S1070428024603522","url":null,"abstract":"<p>[(<i>E</i>)-(3-Aryl-3-oxoprop-1-en-1-yl]triphenylphosphonium bromides react with 2-aminopyridine to form [(2-aryl-3-imidazo-[1,2-<i>a</i>]pyridin-3-yl)methyl]triphenylphosphonium bromides. An alternative reaction scheme is proposed, including the initial attack of the nucleophile on the carbonyl group.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"258 - 262"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830689","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 Maleimides and Itaconimides with Carboxymethyleneazine Binucleophiles
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428024603492
Ya. Yu. Kulichikhina, S. M. Medvedeva, I. V. Nechaev, Yu. A. Kovygin, Kh. S. Shikhaliev, M. A. Present, D. V. Nikitenko
{"title":"Reaction of Maleimides and Itaconimides with Carboxymethyleneazine Binucleophiles","authors":"Ya. Yu. Kulichikhina,&nbsp;S. M. Medvedeva,&nbsp;I. V. Nechaev,&nbsp;Yu. A. Kovygin,&nbsp;Kh. S. Shikhaliev,&nbsp;M. A. Present,&nbsp;D. V. Nikitenko","doi":"10.1134/S1070428024603492","DOIUrl":"10.1134/S1070428024603492","url":null,"abstract":"<p>Reactions of <i>N</i>-arylmaleimides and <i>N</i>-arylitaconimides with carboxymethyleneazines has been studied. The reaction of itaconic acid imides with oxopiperazinylideneacetates and oxomorpholinylidene acetate involve imide recyclization to form pyridine-containing heterosystems. The reaction of <i>N</i>-arylitaconimides and <i>N</i>-arylmaleimides with oxoquinoxalinylidene acetate involves Michael addition to form linear adducts. The features of this process have been explored by means of quantum-chemical calculations.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"239 - 252"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830793","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
Reduction of the Peroxide Products of Cyclooctene Ozonolysis with Sebacic Acid Dihydrazide
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-04-15 DOI: 10.1134/S1070428024604217
M. P. Yakovleva, A. A. Kravchenko, K. A. Saitov, I. S. Nazarov, N. M. Ishmuratova, G. Y. Ishmuratov
{"title":"Reduction of the Peroxide Products of Cyclooctene Ozonolysis with Sebacic Acid Dihydrazide","authors":"M. P. Yakovleva,&nbsp;A. A. Kravchenko,&nbsp;K. A. Saitov,&nbsp;I. S. Nazarov,&nbsp;N. M. Ishmuratova,&nbsp;G. Y. Ishmuratov","doi":"10.1134/S1070428024604217","DOIUrl":"10.1134/S1070428024604217","url":null,"abstract":"<p>The reduction with sebacic acid dihydrazide of the peroxide products of cyclooctene ozonolysis in different solvents leads, depending on the solvent, to three acyclic differently functionalized cyclooctene derivatives: methyl 11,20-dioxo-9,10,21,22-tetraazadocos-8<i>E</i>-enoic acid is formed in methanol, 11,20-dioxo-9,10,21,22-tetraazadocos-8<i>E</i>-enoic acid in methylene chloride, and natural cortic acid in THF.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 2","pages":"263 - 266"},"PeriodicalIF":0.8,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830690","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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