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Interaction of 3,6-Bis(2-pyridyl)-1,2,4,5-tetrazine and 3,4,5,6-Tetrabromo-1,2-dehydrobenzene 3,6-二（2-吡啶基）-1,2,4,5-四嗪与3,4,5,6-四溴-1,2-脱氢苯的相互作用
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602043
S. E. Vatolina, A. P. Krinochkin, A. V. Rybakova, I. A. Khalymbadzha, V. S. Gaviko, D. S. Kopchuk, G. V. Zyryanov
{"title":"Interaction of 3,6-Bis(2-pyridyl)-1,2,4,5-tetrazine and 3,4,5,6-Tetrabromo-1,2-dehydrobenzene","authors":"S. E. Vatolina,&nbsp;A. P. Krinochkin,&nbsp;A. V. Rybakova,&nbsp;I. A. Khalymbadzha,&nbsp;V. S. Gaviko,&nbsp;D. S. Kopchuk,&nbsp;G. V. Zyryanov","doi":"10.1134/S1070428025602043","DOIUrl":"10.1134/S1070428025602043","url":null,"abstract":"<p>The interaction of 3,6-bis(2-pyridyl)-substituted 1,2,4,5-tetrazine with 3,4,5,6-tetrabromo-1,2-dehydrobenzene obtained in situ from the corresponding anthranilic acid was studied for the first time. In this case, instead of the expected product, 5,6,7,8-tetrabromo-1,4-di(2-pyridyl)phthalazine, two alternative transformation products were found, namely 1,2,3,4-tetrabromo-6-methylnaphthalene and 3,6-di(2-pyridyl)pyridazine. The structure of the products was confirmed by physicochemical methods, including X-ray diffraction data. A possible mechanism for this interaction was proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1127 - 1133"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164451","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
Features of Conjugation of Ipidacrine Chloroalkylamides with 5-Acetyl-3-(trifluoromethyl)pyrazole and Its Derivatives. Study of Biological Activity Ipidacrine氯烷基酰胺与5-乙酰-3-（三氟甲基）吡唑及其衍生物的偶联特性。生物活性研究
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602389
O. G. Khudina, D. N. Bazhin, G. F. Makhaeva, Y. V. Burgart, N. V. Kovaleva, N. P. Boltneva, E. V. Rudakova, T. S. Skornyakova, V. I. Saloutin
{"title":"Features of Conjugation of Ipidacrine Chloroalkylamides with 5-Acetyl-3-(trifluoromethyl)pyrazole and Its Derivatives. Study of Biological Activity","authors":"O. G. Khudina,&nbsp;D. N. Bazhin,&nbsp;G. F. Makhaeva,&nbsp;Y. V. Burgart,&nbsp;N. V. Kovaleva,&nbsp;N. P. Boltneva,&nbsp;E. V. Rudakova,&nbsp;T. S. Skornyakova,&nbsp;V. I. Saloutin","doi":"10.1134/S1070428025602389","DOIUrl":"10.1134/S1070428025602389","url":null,"abstract":"<p>An approach to the preparation of ipidacrine conjugates with trifluoromethyl pyrazoles containing acetyl, hydrazone, or oxime groups as functional substituents has been studied. The alkylation of 5-acetyl-3-(trifluoromethyl)pyrazole with 2-chloroacetamide of ipidacrine proceeds non-regioselectively on the nitrogen atoms of the pyrazole ring, giving a mixture of 3-/5-CF<sub>3</sub>-regioisomeric products. The introduction of a hydrazone/oxime substituent into the structure of CF<sub>3</sub>-pyrazoles leads to the preferential formation of 3-CF<sub>3</sub>-regioisomeric conjugates. In alkylation reactions, preservation of the arylhydrazone substituent in pyrazolyl-containing ipidacrines is observed, whereas the oxime group undergoes hydrolysis to the acetyl function. Conjugation of 5-(1-hydrazinylidenethyl)pyrazole with 3-chloropropanamide of ipidacrine is accompanied by partial reduction of the hydrazone substituent. 4-Chlorobutanamide of ipidacrine in MeCN did not react with pyrazoles, and upon heating in DMF, 5-(1-hydrazinylideneethyl)pyrazole underwent transamination to form a symmetric ketazine. The conjugate with the <i>N</i>-propanamide spacer showed moderate selective inhibitory activity towards butyrylcholinesterase (IC<sub>50</sub> = 14.5 ± 0.8 µM) and towards self-aggregation of β-amyloid (1–42). The introduction of an aryl substituent into the hydrazone fragment led to an increase in the antioxidant activity of pyrazoles and to the appearance of significant antioxidant properties of the conjugates in the ABTS (TEAC = 0.47–0.56) and FRAP (0.44–0.55 TE) tests.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1112 - 1126"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165540","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
PREFACE to Special Issues Dedicated to Academician Valentin Pavlovich Ananikov in Honor of His 50th Birthday 为纪念瓦伦丁·帕夫洛维奇·阿纳尼科夫院士50岁生日而写的特刊序言
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025060016
The Editorial Board of the Russian Journal of Organic Chemistry
{"title":"PREFACE to Special Issues Dedicated to Academician Valentin Pavlovich Ananikov in Honor of His 50th Birthday","authors":"The Editorial Board of the Russian Journal of Organic Chemistry","doi":"10.1134/S1070428025060016","DOIUrl":"10.1134/S1070428025060016","url":null,"abstract":"","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"981 - 982"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165541","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
Reactivity Features of ortho-Carboranillithium towards 3,6-Diaryl-1,2,4,5-tetrazines 邻碳硼铵对3,6-二芳基-1,2,4,5-四嗪的反应性特征
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025601578
T. D. Moseev, D. S. Kopchuk, L. A. Smyshliaeva, A. N. Tsmokaluk, P. A. Slepukhin, A. V. Rybakova, M. V. Varaksin, G. V. Zyryanov, V. N. Charushin, O. N. Chupakhin
{"title":"Reactivity Features of ortho-Carboranillithium towards 3,6-Diaryl-1,2,4,5-tetrazines","authors":"T. D. Moseev,&nbsp;D. S. Kopchuk,&nbsp;L. A. Smyshliaeva,&nbsp;A. N. Tsmokaluk,&nbsp;P. A. Slepukhin,&nbsp;A. V. Rybakova,&nbsp;M. V. Varaksin,&nbsp;G. V. Zyryanov,&nbsp;V. N. Charushin,&nbsp;O. N. Chupakhin","doi":"10.1134/S1070428025601578","DOIUrl":"10.1134/S1070428025601578","url":null,"abstract":"<p>The reaction of <i>ortho</i>-carboranilithium with 3,6-di(2-pyridyl)-1,2,4,5-tetrazine, considered as an example of the “from challenging to simple” strategy in the chemistry of carboranes, leads to the previously unknown 3-<i>ortho</i>-carboranyl-[1,2,3]triazolo[1,5-<i>a</i>]pyridine as a result of cleavage of the tetrazine cycle and subsequent formation of the triazole cycle with nitrogen elimination. The structure of the obtained compound was confirmed by the spectroscopic and X-ray diffraction studies. The reaction mechanism, which was additionally confirmed by quantum-chemical calculations of electron densities and the Fukui function, was proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1004 - 1010"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164449","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
Direct C–H Fluorination of N-Heterocycles Promoted by Transition Metals in High Oxidation State 高氧化态过渡金属促进n -杂环直接C-H氟化
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602080
T. V. Gryaznova, K. V. Kholin, M. V. Tarasov, E. L. Gavrilova, Yu. H. Budnikova
{"title":"Direct C–H Fluorination of N-Heterocycles Promoted by Transition Metals in High Oxidation State","authors":"T. V. Gryaznova,&nbsp;K. V. Kholin,&nbsp;M. V. Tarasov,&nbsp;E. L. Gavrilova,&nbsp;Yu. H. Budnikova","doi":"10.1134/S1070428025602080","DOIUrl":"10.1134/S1070428025602080","url":null,"abstract":"<p>A method for obtaining of monofluoro <i>N</i>-heterocycles (pyridines, benzazoles) in the presence of salts of transition metals (nickel, cobalt or silver) in high oxidation states under electrochemical catalytic oxidative conditions is developed. Electrochemical reactions are shown to be effective for the C–H functionalization of heterocyclic substrates. Monitoring of the reaction progress under electrochemical conditions provides mechanistic insight into the C–H functionalization of a heterocycles, which are of interest in medicinal chemistry. It was demonstrated that the electrochemical fluorination results either in 2-fluoro-, or 3-fluorine pyridine depending on the used catalyst.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1180 - 1188"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164450","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 Antioxidant Properties of 1,3,4-Oxadiazole Derivatives of Benzoic and Monohydroxybenzoic Acids 苯甲酸和单羟基苯甲酸类1,3,4-恶二唑衍生物的合成及抗氧化性能
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602456
I. E. Mikhailov, N. I. Belaya, A. V. Belyi, Yu. M. Artyushkina, G. A. Dushenko, V. I. Minkin
{"title":"Synthesis and Antioxidant Properties of 1,3,4-Oxadiazole Derivatives of Benzoic and Monohydroxybenzoic Acids","authors":"I. E. Mikhailov,&nbsp;N. I. Belaya,&nbsp;A. V. Belyi,&nbsp;Yu. M. Artyushkina,&nbsp;G. A. Dushenko,&nbsp;V. I. Minkin","doi":"10.1134/S1070428025602456","DOIUrl":"10.1134/S1070428025602456","url":null,"abstract":"<p>2-Aryl- and 2-aryl-5-alkyl-1,3,4-oxadiazoles were synthesized by the interaction of benzoic acid hydrazides with orthoesters of carboxylic acids, and their antiradical action was studied in the reaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH<sup>•</sup>). In the reaction with DPPH<sup>•</sup>, phenoloxadiazoles showed higher antiradical activity compared to the corresponding monohydroxybenzoic acids due to intramolecular synergism, which is a result of the combined action of the phenol and oxadiazole fragments within one molecule, leading to resonance stabilization of the resulting phenoxyl radical. For 1,3,4-oxadiazoles, which do not contain a phenolic fragment in their composition and exhibit lower antiradical activity compared to phenoloxadiazoles, a mechanism of their antioxidant action has been proposed, which is associated with the formation of a radical adduct.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1099 - 1111"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165542","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
Cross-Coupling Reactions of Organometallic Derivatives of Nitronyl Nitroxides with Aryl Halides Catalyzed by Palladium Complexes (A Review) 钯配合物催化硝基氮氧化物有机金属衍生物与芳基卤化物的交叉偶联反应（综述）
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025601608
I. A. Zayakin, A. M. Zimina, E. V. Tretyakov
{"title":"Cross-Coupling Reactions of Organometallic Derivatives of Nitronyl Nitroxides with Aryl Halides Catalyzed by Palladium Complexes (A Review)","authors":"I. A. Zayakin,&nbsp;A. M. Zimina,&nbsp;E. V. Tretyakov","doi":"10.1134/S1070428025601608","DOIUrl":"10.1134/S1070428025601608","url":null,"abstract":"<p>Sterically hindered 2-imidazoline-3-oxide-1-oxyls (nitronyl nitroxides) are a class of organic radicals that are widely used in the field of molecular design of magnets and spintronic devices. Over the past decade, the most significant advances in the chemistry and function-oriented synthesis of nitronyl nitroxide radicals have been achieved through palladium-catalyzed cross-coupling reaction of organometallic derivatives of nitronyl nitroxides with aryl halides. The review presents the development of this field, the challenges encountered in the application of the cross-coupling reaction in the chemistry of nitronyl nitroxides, and the solutions found that made it possible to implement the targeted synthesis of organic high-spin systems.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1011 - 1033"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165544","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
Photocatalytic Fluoroalkylation of Derivatives of 3-Aminopyrazole 3-氨基吡唑衍生物的光催化氟烷基化反应
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602262
D. S. Koltun, V. V. Levin, A.D. Dilman
{"title":"Photocatalytic Fluoroalkylation of Derivatives of 3-Aminopyrazole","authors":"D. S. Koltun,&nbsp;V. V. Levin,&nbsp;A.D. Dilman","doi":"10.1134/S1070428025602262","DOIUrl":"10.1134/S1070428025602262","url":null,"abstract":"<p>The reaction of 3-aminopyrazole derivatives with pentafluoroethyl iodide in the presence of a ruthenium photocatalyst under blue light irradiation is described. 3-Aminopyrazoles bearing a substituent at position 4 or 5 yielded the corresponding fluoroalkylation products. In the case of N-Boc derivatives of 3-aminopyrazole, the selectivity of radical fluoroalkylation depended on the structure of the N-Boc pyrazole.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1076 - 1080"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165551","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
Late-Stage C–H Functionalization of Nimesulide via (Nimesulide)(3,5-dimethylisoxazol-4-yl)iodonium Salt Formation 尼美舒利通过（尼美舒利）（3,5-二甲基异恶唑-4-基）碘盐形成的后期C-H功能化
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S107042802560192X
D. I. Bugaenko, A. V. Karchava
{"title":"Late-Stage C–H Functionalization of Nimesulide via (Nimesulide)(3,5-dimethylisoxazol-4-yl)iodonium Salt Formation","authors":"D. I. Bugaenko,&nbsp;A. V. Karchava","doi":"10.1134/S107042802560192X","DOIUrl":"10.1134/S107042802560192X","url":null,"abstract":"<p>The reaction of N-methylated nimesulide with Koiser’s reagent based on 4-iodo-3,5-dimethylisoxazole (DMIX-I(OH)OTs) yielded the corresponding iodonium salt. Subsequent interaction of this salt with S-, O-, and N-nucleophiles gave functionalized derivatives of nimesulide.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1081 - 1088"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165596","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 New 2-Carboxamide-Substituted 5-Oxo-5,6-dihydro-4H-1,3,4-thiadiazines 新2-羧基酰胺取代5-氧-5,6-二氢- 4h -1,3,4-噻二嗪的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602766
M. A. Prezent, S. V. Baranin, I. V. Zavarzin
{"title":"Synthesis of New 2-Carboxamide-Substituted 5-Oxo-5,6-dihydro-4H-1,3,4-thiadiazines","authors":"M. A. Prezent,&nbsp;S. V. Baranin,&nbsp;I. V. Zavarzin","doi":"10.1134/S1070428025602766","DOIUrl":"10.1134/S1070428025602766","url":null,"abstract":"<p>Based on the reaction of benzylmaleimide and N-substituted 2-hydrazinyl-2-thioxoacetamide, a series of new 2-carboxamide-substituted 5-oxo-5,6-dihydro-4<i>H</i>-1,3,4-thiadiazines, compounds with potential biological activity, were synthesized and characterized.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"984 - 987"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164453","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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