M. P. Shurygina, M. V. Arsenyev, E. V. Baranov, M. A. Baten’kin, M. Yu. Zakharina, E. R. Zhiganshina, A. N. Konev, S. A. Chesnokov
{"title":"Synthesis and properties of a new photoinitiator of polymerization by visible irradiation based on 3,5-di-tert-butyl-o-benzoquinone","authors":"M. P. Shurygina, M. V. Arsenyev, E. V. Baranov, M. A. Baten’kin, M. Yu. Zakharina, E. R. Zhiganshina, A. N. Konev, S. A. Chesnokov","doi":"10.1007/s11172-024-4460-y","DOIUrl":"10.1007/s11172-024-4460-y","url":null,"abstract":"<div><p>A new sterically hindered trialkyl-substituted <i>o</i>-benzoquinone, 4,6-di-<i>tert</i>-butyl-3-[(3,5-di-<i>tert</i>-butyl-1<i>H</i>-pyrazol-1-yl)methyl]cyclohexane-3,5-diene-1,2-dione was synthesized. Its spectral, electronic, and structural characteristics were determined, which were found to be similar to those for analogous 3,6- and 3,5-di-<i>tert</i>-butyl-<i>o</i>-benzoquinones. The following sequence was observed for the reactivity in the photoreduction reaction in the presence of <i>N,N</i>-dimethylaniline (DMA): 3,6-di-<i>tert</i>-butyl-<i>o</i>-benzoquinone > 4,6-di-<i>tert</i>-butyl-3-[(3,5-di-<i>tert</i>-butyl-1<i>H</i>-pyrazol-1-yl)methyl]cyclohexane-3,5-diene-1,2-dione > 3,5-di-<i>tert</i>-butyl-<i>o</i>-benzoquinone. The new quinone, like 3,6- and 3,5-di-<i>tert</i>-butyl-<i>o</i>-benzoquinones, in combination with DMA was found to initiate radical polymerization under the irradiation by LED sources in the range from 395 to 630 nm. It was found that the introduction of the pyrazole-containing fragment at position 6 of the quinonoid ring of 3,5-di-<i>tert</i>-butyl-<i>o</i>-benzoquinone led to a sharp increase in the activity of the new compound as a photoinitiator compared to 3,5-di-<i>tert</i>-butyl-<i>o</i>-benzoquinone and made the new quinone comparable with 3,6-di-<i>tert</i>-butyl-<i>o</i>-benzoquinone in the photoinitiating activity. At the same time, a photopolymerizable composition containing a photoinitiating system based on 4,6-di-<i>tert</i>-butyl-3-[(3,5-di-<i>tert</i>-butyl-1<i>H</i>-pyrazol-1-yl)methyl]cyclohexane-3,5-diene-1,2-dione was found to be more stable than the photoinitiating system based on 3,6-di-<i>tert</i>-butyl-<i>o</i>-benzoquinone.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3429 - 3440"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976422","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. A. Slesarenko, G. Z. Tulibaeva, A. V. Yudina, N. A. Slesarenko, A. F. Shestakov, O. V. Yarmolenko
{"title":"Low-temperature gelled electrolytes based on the salt LiN(SO2CF3)2 in mixed glyme solutions for lithium power sources","authors":"A. A. Slesarenko, G. Z. Tulibaeva, A. V. Yudina, N. A. Slesarenko, A. F. Shestakov, O. V. Yarmolenko","doi":"10.1007/s11172-024-4442-0","DOIUrl":"10.1007/s11172-024-4442-0","url":null,"abstract":"<div><p>New low-temperature gelled electrolytes based on 1 <i>M</i> LiN(SO<sub>2</sub>CF<sub>3</sub>)<sub>2</sub> in mixed solutions of glymes and 1,3-dioxolane with the addition of 1 wt.% polyethylene oxide (PEO) were obtained. The conductometry method was used to demonstrate that all the compositions have a conductivity of 7–8 and 3–4 mS cm<sup>−1</sup> at 20 at −20 °C, respectively. The interface between the electrolyte and the metallic lithium was investigated using electrochemical impedance spectroscopy. The composition 1 <i>M</i> LiN(SO<sub>2</sub>CF<sub>3</sub>)<sub>2</sub> in a mixture of dioxolane—dimethoxyethane—diglyme—tetraglyme (1: 2: 2: 1 v/v) + 1 wt.% PEO was found to be the best for low temperatures. Quantum chemical modeling of solvate complexes of the Li<sup>+</sup> cation was used to propose a mechanism for improving ion transport from glyme solvates along the PEO chain.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3267 - 3274"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976468","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. L. Baklagin, V. V. Bukhalin, E. A. Smirnova, I. G. Abramov, S. I. Filimonov, S. A. Ivanovsky, K. Yu. Suponitsky
{"title":"Synthesis of condensed dibenzo[b,f]pyrimido[1,6-d][1,4]oxazepines based on Biginelli products","authors":"V. L. Baklagin, V. V. Bukhalin, E. A. Smirnova, I. G. Abramov, S. I. Filimonov, S. A. Ivanovsky, K. Yu. Suponitsky","doi":"10.1007/s11172-024-4451-z","DOIUrl":"10.1007/s11172-024-4451-z","url":null,"abstract":"<div><p>A method for the synthesis of substituted dibenzo[<i>b,f</i>]pyrimido[1,6-<i>d</i>][1,4]oxazepines fused with the Biginelli products was proposed. This condensation was accomplished by the aromatic nucleophilic substitution reaction between 4,5-dichlorophthalonitrile or 4-bromo-5-nitrophthalonitrile and the salicylaldehyde-based Biginelli products.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3352 - 3358"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976436","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}
{"title":"Synthesis of new N-substituted octahydrothieno[3,4-b]pyrazine 6,6-dioxide derivatives","authors":"M. A. Prezent, S. V. Baranin, Yu. N. Bubnov","doi":"10.1007/s11172-024-4429-x","DOIUrl":"10.1007/s11172-024-4429-x","url":null,"abstract":"<div><p>A series of new <i>N</i>-substituted derivatives of octahydrothieno[3,4-<i>b</i>]pyrazine 6,6-dioxide were synthesized for further biological screening.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"3104 - 3108"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778414","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}
{"title":"Available strategies for the synthesis of indenes for metal complex catalysis","authors":"V. B. Kharitonov, D. A. Loginov","doi":"10.1007/s11172-024-4395-3","DOIUrl":"10.1007/s11172-024-4395-3","url":null,"abstract":"<div><p>Simple and available methods for the synthesis of indene derivatives, mainly alkyl- and aryl-substituted indenes, which are most sought after as ligands for the development of catalysts based on transition metal complexes, are summarized. The review covers synthetic approaches including both the assembly of the indene structure from acyclic or monocyclic precursors and the functionalization of the indene framework or related compounds, such as benzofulvenes, indanones, indanes, indenones, fluorenes, <i>etc</i>. However, we excluded from our consideration the multi-step synthetic pathways and those which require commercially unavailable precursors and reagents.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2787 - 2800"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778418","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}
{"title":"(Tetramethylcyclobutadiene)cobalt complexes with arene ligands. Arene replacement: X-ray diffraction and quantum chemical studies","authors":"D. A. Loginov, Yu. V. Nelyubina","doi":"10.1007/s11172-024-4403-7","DOIUrl":"10.1007/s11172-024-4403-7","url":null,"abstract":"<div><p>The structures of the complexes [Cb*Co(η<sup>6</sup>-indane)] • PF<sub>6</sub> (<b>1</b> • PF<sub>6</sub>, Cb* = C<sub>4</sub>Me<sub>4</sub>) and [Cb*Co(η<sup>6</sup>-naphthalene)] • PF<sub>6</sub> (<b>2</b> • PF<sub>6</sub>) were determined by X-ray diffraction. The dissociation energies of Co—arene bonds in cations <b>1</b> and <b>2</b> and in related derivatives containing benzene, <i>o</i>-xylene, and anthracene ligands were estimated by DFT calculations. The effect of substituents in the arene ligand on the direction of the nucleophilic attack by acetonitrile during the arene replacement was analyzed.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2866 - 2871"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778431","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}
B. P. Gladkikh, D. V. Danilov, V. S. D’yachenko, E. S. Il’ina, G. M. Kurunina, G. M. Butov, I. A. Novakov
{"title":"Synthesis and properties of 1,1′-(alkane-1,n-diyl)bis[3-(3,5,7-trifluoroadamantan-1-yl)ureas]","authors":"B. P. Gladkikh, D. V. Danilov, V. S. D’yachenko, E. S. Il’ina, G. M. Kurunina, G. M. Butov, I. A. Novakov","doi":"10.1007/s11172-024-4411-7","DOIUrl":"10.1007/s11172-024-4411-7","url":null,"abstract":"<div><p>New 1,1′-(alkane-1,<i>n</i>-diyl)bis[3-(3,5,7-trifluoroadamantan-1-yl)ureas] were obtained by the reaction of 1,3,5-trifluoroadamantane-7-isocyanate with aliphatic diamines in 71–92% yields. For the first time, the influence of the number of fluorine atoms in the adamantyl substituent on the melting point, lipophilicity, and water solubility of the ureas was established, which allows one to purposefully regulate the important properties of ureas as potential enzyme inhibitors. Using molecular docking, their possible efficiency in the inhibition of such targets as p38 MAPK, c-Raf, and hsEH was shown.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2941 - 2947"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778480","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. O. Kushch, M. V. Goryaeva, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin
{"title":"Three-component domino reactions in the synthesis of polyfluoroalkyl-containing tetrahydropyrido[2,1-b]quinazolines","authors":"S. O. Kushch, M. V. Goryaeva, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin","doi":"10.1007/s11172-024-4413-5","DOIUrl":"10.1007/s11172-024-4413-5","url":null,"abstract":"<div><p>The three-component reaction of polyfluoroalkyl-3-oxo esters with α,β-unsaturated aldehydes and 2-(aminomethyl)aniline afforded 8-(polyfluoro-1-hydroxyalkyl)-6,7,8,11-tetrahydro-9<i>H</i>-pyrido[2,1-<i>b</i>]quinazolin-9-ones upon heating; under mild conditions, this reaction gave bicyclic dihydroquinazoline intermediates, CF<sub>3</sub> derivatives of which exist in the form of bases and their C<sub>2</sub>F<sub>5</sub> analogues exist in the form of salts. The diastereomeric and tautomeric structures of the new heterocycles were studied by <sup>1</sup>H, <sup>19</sup>F, and <sup>13</sup>C NMR spectroscopy, IR spectroscopy, and X-ray diffraction. A domino mechanism for their formation was proposed.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2953 - 2967"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778482","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. F. Mironov, A. V. Nemtarev, M. N. Dimukhametov, T. A. Baronova, A. T. Gubaidullin, I. A. Litvinov, S. A. Katsuba, T. I. Burganov
{"title":"Synthesis and structures of 1-phosphaindene derivatives with five- and four-coordinate phosphorus atom","authors":"V. F. Mironov, A. V. Nemtarev, M. N. Dimukhametov, T. A. Baronova, A. T. Gubaidullin, I. A. Litvinov, S. A. Katsuba, T. I. Burganov","doi":"10.1007/s11172-024-4416-2","DOIUrl":"10.1007/s11172-024-4416-2","url":null,"abstract":"<div><p>The reactions of 1,1,1,2,3-pentachloro-1-phosphaindene <b>(1)</b> with phenylacetylene and catechol were found to lead to the regioselective formation of the addition product, 1,1,2,3-tetrachloro-1-(2-chloro-2-phenylvinyl)-1-phosphaindene <b>(6)</b>, and spirophosphorane, 1,2-bis{(2′,3′-dichloro-2<i>H</i>-2λ<sup>5</sup>-spiro[benzo[<i>d</i>][1,3,2]dioxaphosphole-2,1′-phosphaindene]-2-yl)oxy}benzene <b>(13)</b>. The hydrolysis of compound <b>6</b> proceeds through the intermediate formation of (<i>Z</i>)-2,3-dichloro-1-(2-chloro-2-phenylvinyl)phosphaindene 1-oxide <b>(9)</b> and affords the P—C bond cleavage product, [(<i>Z</i>)-2-chloro-2-phenylvinyl]-{(2-[(<i>Z</i>)-1,2-dichlorovinyl]phenyl}phosphinic acid <b>(10)</b>. The structures of compounds <b>1, 6</b>, and <b>13</b> were determined by X-ray diffraction. Compound <b>6</b> is the first example of monocyclic phosphoranes containing the phosphorus atom in a nearly ideal trigonal-bipyramidal configuration with an antiapicophilic (diequatorial) arrangement of the five-membered ring at the base. Quantum chemical calculations showed that this structure is favorable due to conjugation effects. Compound <b>13</b> has a planar chirality in the crystal (space group <i>P</i>2<sub>1</sub>).</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2987 - 3011"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778485","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}
{"title":"Epigenetic aspects of a putative mechanism of antitumor action of ferrocenylalkylazoles","authors":"V. N. Babin, Yu. A. Belousov, V. N. Kulikov","doi":"10.1007/s11172-024-4397-1","DOIUrl":"10.1007/s11172-024-4397-1","url":null,"abstract":"<div><p>The results of antitumor assays of ferrocenylalkylazoles and possible mechanisms of their biological activity were analyzed. A model of the antitumor action of ferrocenylalkylazoles was proposed, according to which ferrocenylalkylation of nitrogenous bases of the tumor cell DNA takes place, resulting in a change in the epigenetic regulation and in the initiation of apoptosis.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"2815 - 2820"},"PeriodicalIF":1.7,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142778420","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}