I. S. Odin, R. N. Itakhunov, D. M. Gusev, A. V. Vologzhanina, A. A. Golovanov
{"title":"Synthesis of 5-(1H-pyrazol-3-yl)isoxazoles","authors":"I. S. Odin, R. N. Itakhunov, D. M. Gusev, A. V. Vologzhanina, A. A. Golovanov","doi":"10.1007/s11172-024-4381-9","DOIUrl":"10.1007/s11172-024-4381-9","url":null,"abstract":"<div><p>5-(4,5-Dihydro-1<i>H</i>-pyrazol-3-yl)isoxazoles (pyrazoline-isoxazoles) are readily oxidized by active manganese dioxide in benzene or dichloromethane at room temperature. As a result, a simple and efficient method for the synthesis of the corresponding pyrazoleisoxazoles in 94–99% yields was developed. It was shown that 3-ethynyl-1<i>H</i>-pyrazoles are inactive in the 1,3-dipolar cycloaddition reaction with nitrile oxides and nitrile imines. The synthesized di- and trisubstituted pyrazole-isoxazoles showed weaker luminescent properties compared to pyrazoline-isoxazoles.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2687 - 2692"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518856","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}
Zhihui Yang, Xiaochen Wang, Yuanrong Wang, Jinyun Yang, Haifeng Lu
{"title":"A novel route for the synthesis of phosphonate-containing siloxanes by the catalyst-free Kabachnik—Fields reaction","authors":"Zhihui Yang, Xiaochen Wang, Yuanrong Wang, Jinyun Yang, Haifeng Lu","doi":"10.1007/s11172-024-4385-5","DOIUrl":"10.1007/s11172-024-4385-5","url":null,"abstract":"<div><p>A new route for the synthesis of siloxanes containing substituents with the phosphonate and amino groups based on the catalyst-free Kabachnik—Fields reaction was developed. The synthesis was accomplished under mild conditions using 3-aminopropylsilanes, cyclic ketones, and diethyl phosphite as the starting materials to give the corresponding 1-(3-silylpropylamino)cycloalkylphosphonates in high yields.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2725 - 2729"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518756","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}
O. P. Papeta, I. N. Zubkov, V. M. Chernyshev, D. V. Chernysheva, E. M. Bayan, A. P. Savost’yanov, A. N. Saliev, M. R. Agliullin, R. E. Yakovenko
{"title":"Conversion of syngas to hydrocarbons using bifunctional cobalt catalysts containing HZSM-5 zeolites of various porous structures","authors":"O. P. Papeta, I. N. Zubkov, V. M. Chernyshev, D. V. Chernysheva, E. M. Bayan, A. P. Savost’yanov, A. N. Saliev, M. R. Agliullin, R. E. Yakovenko","doi":"10.1007/s11172-024-4371-y","DOIUrl":"10.1007/s11172-024-4371-y","url":null,"abstract":"<div><p>New bifunctional composite catalysts for the Fischer—Tropsch synthesis were developed on the basis of a mixture of the Co—Al<sub>2</sub>O<sub>3</sub>/SiO<sub>2</sub> catalyst, meso-HZSM-5 hierarchical mesoporous zeolite, and boehmite binder. The mesoporous zeolite was obtained by alkaline treatment of the industrial HZSM-5 zeolite. The developed catalysts are suitable for one-pot conversion of syngas into linear C<sub>5+</sub> hydrocarbons, which then undergo cracking and isomerization reactions. The effect of the concentration of NaOH solution on the porosity and catalytic efficiency of the obtained meso-HZSM-5 zeolite was studied. The performances of the bifunctional catalysts obtained from alkali-treated and pristine HZSM-5 in the conversion of syngas were compared. In the presence of the catalyst based on the alkali-treated zeolite, the total productivity to C<sub>5+</sub> hydrocarbons somewhat decreases. However, the increase in the total yield of branched and unsaturated hydrocarbons provides the formation of motor fuels with high anti-knock properties.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2606 - 2615"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518821","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}
G. B. Eshova, Dzh. A. Davlatshoeva, F. Miraminzoda
{"title":"Distribution diagrams and stability of alanine coordination compounds of FeII and FeIII","authors":"G. B. Eshova, Dzh. A. Davlatshoeva, F. Miraminzoda","doi":"10.1007/s11172-024-4377-5","DOIUrl":"10.1007/s11172-024-4377-5","url":null,"abstract":"<div><p>The formation of mononuclear complexes and a heterovalent compound in the Fe<sup>II</sup>—Fe<sup>III</sup>—<span>l</span>-Ala—H<sub>2</sub>O system was observed when using the Clark—Nikolsky oxidation potential at a temperature of 298.15 K and an ionic strength of the (Na(H)ClO<sub>4</sub>) solution equal to 0.75 mol L<sup>−1</sup>. The method of successive approximations (iteration) of the Yusupov oxidation function was used to calculate the stability and the model parameters of the mononuclear coordination compounds [FeHL(H<sub>2</sub>O)<sub>5</sub>]<sup>3+</sup>, [Fe(HL)<sub>2</sub>(H<sub>2</sub>O)<sub>4</sub>]<sup>3+</sup>, [Fe<sub>2</sub>(HL)<sub>2</sub>(OH)<sub>4</sub>(H<sub>2</sub>O)<sub>6</sub>]<sup>2+</sup>, [Fe<sup>III</sup>Fe<sup>II</sup>(HL)<sub>2</sub>(OH)<sub>4</sub>(H<sub>2</sub>O)<sub>6</sub>]<sup>+</sup>, [FeHL(H<sub>2</sub>O)<sub>5</sub>]<sup>2+</sup>, [Fe(HL)(OH)(H<sub>2</sub>O)<sub>4</sub>]<sup>+</sup>, and [Fe(HL)(OH)<sub>2</sub>(H<sub>2</sub>O)<sub>3</sub>]<sup>0</sup> (L is an alanine ligand), the formation constants of these complexes, to determine the regions where they are dominant and their maximum degrees of accumulation, as well as to plot the diagrams of their distribution as a function of pH. It was determined that the heterovalent complex is the most stable and dominates up to pH 9.5.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2652 - 2659"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518755","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}
M. B. Gazizov, R. A. Khairullin, S. Yu. Ivanova, R. F. Karimova, B. D. Nuriakhmetov, O. D. Khairullina, L. R. Shaikhutdinova, N. N. Gazizova
{"title":"Reactions of phosphorus (iv) and orthocarboxylic acid esters with benzal and benzyl halides: pathways and catalysis","authors":"M. B. Gazizov, R. A. Khairullin, S. Yu. Ivanova, R. F. Karimova, B. D. Nuriakhmetov, O. D. Khairullina, L. R. Shaikhutdinova, N. N. Gazizova","doi":"10.1007/s11172-024-4382-8","DOIUrl":"10.1007/s11172-024-4382-8","url":null,"abstract":"<div><p>The main pathway of the reaction of benzal and benzyl halides with phosphorus(<span>iv</span>) acid esters followed the dehalophosphonyl/phosphinyl(oxylation) course and led to the corresponding carbonyl-containing compounds or benzyl esters. A new reaction between α-chloro ethers and <i>O</i>-alkyl diethylphosphinates was discovered. The reactions of benzyl halides with esters of phosphorus(<span>iv</span>) and orthocarboxylic acids were catalyzed by anhydrous zinc chloride.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2693 - 2700"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518857","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}
Yu. M. Selivantev, V. S. Mityanov, E. S. Uvarova, F. A. Kolokolov, A. N. Morozov, O. A. Raitman
{"title":"Interaction of 2-unsubstituted imidazole N-oxides with electron-deficient olefins: a quantum chemical analysis","authors":"Yu. M. Selivantev, V. S. Mityanov, E. S. Uvarova, F. A. Kolokolov, A. N. Morozov, O. A. Raitman","doi":"10.1007/s11172-024-4370-z","DOIUrl":"10.1007/s11172-024-4370-z","url":null,"abstract":"<div><p>Reactions between the model compound <i>N</i>-1,4,5-trimethyl-1<i>H</i>-imidazole-3-oxide and electron-deficient olefins including 2-(4-methoxybenzylidene)malononitrile, (<i>E</i>)-ethyl-2-cyano-3-(4-methoxyphenyl)acrylate, 2-benzoyl-3-(4-methoxyphenyl)acrylonitrile, and 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione were theoretically studied in terms of the density functional theory. It was demonstrated that the reactions can proceed either by the 1,3-dipolar cycloaddition mechanism or by the Michael addition mechanism depending on the type of electron-withdrawing substituents in the olefin molecule. The reaction pathways were calculated and the intermediate structures were determined.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2593 - 2605"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518735","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}
S. Yu. Vostruhina, A. N. Reznikov, Yu. N. Klimochkin
{"title":"Palladium-catalyzed cyclization of N-(2-iodophenyl)acrylamides and hydrophosphoryl compounds in the presence of (R,R)-DIOP and (S)-Monophos ligands","authors":"S. Yu. Vostruhina, A. N. Reznikov, Yu. N. Klimochkin","doi":"10.1007/s11172-024-4383-7","DOIUrl":"10.1007/s11172-024-4383-7","url":null,"abstract":"<div><p>3-Phosphorylmethyl-3-R-indolin-2-ones were synthesized by the cascade Heck cyclization—phosphorylation of <i>N</i>-(2-iodophenyl)acrylamides and hydrophosphoryl compounds. In the presence of the PdCl<sub>2</sub>/(<i>S</i>)-Monophos catalytic system, a racemic product was obtained; while, the (<i>R,R</i>)-DIOP ligand provided small chiral induction (up to 15% <i>ee</i>).</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2701 - 2707"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518759","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}
A. Yu. Potapov, A. A. Skoptsova, N. P. Novichikhina, N. A. Podoplelova, M. A. Panteleev, Kh. S. Shikhaliev
{"title":"Synthesis and anticoagulant activity of methyl 2-{2-[2-(4,4,6-trimethyl-2-oxo-4H-pyrrolo[3,2,1-ij]quinolin-1(2H)-ylidene)hydrazineyl]-4-oxothiazol-5(4H)-ylidene}acetates against blood clotting factors Xa, XIa and thrombin","authors":"A. Yu. Potapov, A. A. Skoptsova, N. P. Novichikhina, N. A. Podoplelova, M. A. Panteleev, Kh. S. Shikhaliev","doi":"10.1007/s11172-024-4390-8","DOIUrl":"10.1007/s11172-024-4390-8","url":null,"abstract":"<div><p>The sequential reaction of differently substituted 4,4,6-trimethyl-4<i>H</i>-pyrrolo[3,2,1-<i>ij</i>]-quinoline-1,2-diones with thiosemicarbazide and dimethyl acetylenedicarboxylate yielded a series of new 2-{2-[2-(4,4,6-trimethyl-2-oxo-4<i>H</i>-pyrrolo[3,2,1-<i>ij</i>]quinolin-1(2<i>H</i>)-ylidene)hydrazineyl]-4-oxothiazol-5(4<i>H</i>)-ylidene}acetates, 2-{[(1-{2-[5-(2-methoxy-2-oxoethylidene)-4-oxo-4,5-dihydrothiazol-2-yl]hydrazineylidene}-4,4-dimethyl-2-oxo-1,2-dihydro-4<i>H</i>-pyrrolo[3,2,1-<i>ij</i>]quinolin-6-yl)methyl]thio}benzoic acids, and 2-{[(1-{2-[5-(2-methoxy-2-oxoethylidene)-4-oxo-4,5-dihydrothiazol-2-yl]hydrazineyl-idene}-4,4-dimethyl-2-oxo-1,2-dihydro-4<i>H</i>-pyrrolo[3,2,1-<i>ij</i>]quinolin-6-yl)methyl]thio}-nicotinic acids. The synthesized compounds were isolated as single isomers having presumably the <i>Z,Z</i> configuration. Primary <i>in vitro</i> screening of inhibitory activity of the synthesized compounds against blood clotting factors Xa, XIa and thrombin was carried out. Efficient dual inhibitors of factors Xa and XIa and factor Xa and thrombin were identified.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2765 - 2771"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518764","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}
V. V. Baranov, M. M. Antonova, S. A. Aksenova, A. N. Kravchenko
{"title":"Synthesis of 3a,4,6a-triphenylimidazothiazoledione and 2-thioxo-3a,6,6a-triphenylimidazooxazolone in the reaction of 5-hydroxy-1,4,5-triphenyl-1H-imidazol-2(5H)-one with KSCN and AcOH","authors":"V. V. Baranov, M. M. Antonova, S. A. Aksenova, A. N. Kravchenko","doi":"10.1007/s11172-024-4391-7","DOIUrl":"10.1007/s11172-024-4391-7","url":null,"abstract":"<div><p>The study of the reaction of 5-hydroxy-1,4,5-triphenyl-1<i>H</i>-imidazol-2(5<i>H</i>)-one with KSCN and AcOH showed that it leads to the formation of 3a,4,6a-triphenyltetrahydro-2<i>H</i>-imidazo[4,5-<i>d</i>]thiazole-2,5(3<i>H</i>)-dione (<b>1a</b>) and 2-thioxo-3a,6,6a-triphenyltetrahydro-2<i>H</i>-imidazo[4,5-<i>d</i>]oxazol-5(3<i>H</i>)-one (<b>2b</b>) with the predominant formation of the former one. The structures of compounds <b>1a</b> and <b>2b</b> were confirmed by X-ray diffraction analysis on the examples of solvate <b>1a</b> • AcOH and monohydrate <b>2b</b> • H<sub>2</sub>O obtained by crystallization from AcOH and a mixture of EtOH—H<sub>2</sub>O (1: 10), respectively.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 9","pages":"2772 - 2777"},"PeriodicalIF":1.7,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142518762","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}
A. P. Krinochkin, D. S. Kopchuk, M. I. Valieva, E. S. Starnovskaya, Ya. K. Shtaitz, G. A. Kim, N. V. Slovesnova, A. S. Minin, A. V. Belousova, V. A. Pozdina, I. S. Kovalev, G. V. Zyryanov, A. N. Tsmokalyuk, I. L. Nikonov, V. L. Rusinov
{"title":"New europium complexes of C(6)-DTTA-appended 5-aryl-2,2′-bipyridines: synthesis, luminescence, and evaluation of their activity against cell culture","authors":"A. P. Krinochkin, D. S. Kopchuk, M. I. Valieva, E. S. Starnovskaya, Ya. K. Shtaitz, G. A. Kim, N. V. Slovesnova, A. S. Minin, A. V. Belousova, V. A. Pozdina, I. S. Kovalev, G. V. Zyryanov, A. N. Tsmokalyuk, I. L. Nikonov, V. L. Rusinov","doi":"10.1007/s11172-024-4343-2","DOIUrl":"10.1007/s11172-024-4343-2","url":null,"abstract":"<div><p>New 5-[4(3)-R-phenyl]-2,2′-bipyridines bearing the 1,1,7,7-tetrakis(<i>tert</i>-butoxycarbonylmethyl)-1,4,7-triazaheptane (DTTA) moiety at the C(6) position (R = Cl, Br, CF<sub>3</sub>) and their water-soluble Eu<sup>III</sup> complexes were synthesized. The photophysical properties of the synthesized complexes were investigated. More efficient sensitization of Eu<sup>3+</sup> cation luminescence was demonstrated for a number of halogen-containing ligands. Some chelates exhibited moderate cell-staining ability. The synthesized compounds did not show significant photodynamic activity, which may be due to the inhibition of the <i>in situ</i> generation of reactive oxygen species <i>via</i> the supposed interaction with the methylene moiety of DTTA-appended 2,2′-bipyridine ligands.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2216 - 2227"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267577","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}