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Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety 基于具有 (Z,Z)-1,5 二烯分子的新型 ω-hydroxyalkadienoic acids 的大环单二元醇化合物的合成
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-07-26 DOI: 10.1007/s11172-024-4278-7
I. I. Islamov, I. V. Gaisin, U. M. Dzhemilev, V. A. D’yakonov
{"title":"Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety","authors":"I. I. Islamov, I. V. Gaisin, U. M. Dzhemilev, V. A. D’yakonov","doi":"10.1007/s11172-024-4278-7","DOIUrl":"https://doi.org/10.1007/s11172-024-4278-7","url":null,"abstract":"<p>A stereoselective synthesis of new (6<i>Z</i>,10<i>Z</i>)-16-hydroxyhexadeca-6,10-dienoic and (7<i>Z</i>,11<i>Z</i>)-18-hydroxyoctadeca-7,11-dienoic acid that involved the Ti-catalyzed homocyclomagnesiation of the functionally substituted 1,2-dienes was developed. Subsequent intramolecular cyclization of the synthesized ω-hydroxyalkadienoic acids in the presence of catalytic amounts (2.5–10 mol.%) of hafnium(<span>iv</span>) triflate gave unsaturated macrocyclic lactones and diolides with pharmacophoric 1<i>Z</i>,5<i>Z</i>-diene moieties.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784872","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
One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones 一锅形成六个键：含吡啶的哌啶-2-酮的伪六组份非对映选择性合成
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4242-6
A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin
{"title":"One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones","authors":"A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin","doi":"10.1007/s11172-024-4242-6","DOIUrl":"https://doi.org/10.1007/s11172-024-4242-6","url":null,"abstract":"<p>The present study describes a multicomponent synthesis of pyridinium derivatives of piperidin-2-ones from aromatic aldehydes, malononitriles, pyridines, haloacetates, and ammonium acetate. The synthesis occurs through the <i>in situ</i> formation of pyridinium ylide and involves the Knoevenagel—Michael—Mannich cyclization cascade. 1-[(3<i>RS</i>,4<i>SR</i>,6<i>RS</i>)-4,6-Diaryl-5,5-dicyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with three stereocenters and 1-[(3<i>RS</i>,4<i>SR</i>,5<i>SR</i>,6<i>RS</i>)-5-alkoxycarbonyl-4,6-diaryl-5-cyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with four stereocenters were synthesized.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510067","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 N-(iminyl)pyridinium salts from hydrazones by the Zincke reaction 利用锌克反应从酰肼合成 N-(亚氨基)吡啶鎓盐
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4246-2
E. A. Ilin, V. O. Smirnov, A. D. Dilman
{"title":"Synthesis of N-(iminyl)pyridinium salts from hydrazones by the Zincke reaction","authors":"E. A. Ilin, V. O. Smirnov, A. D. Dilman","doi":"10.1007/s11172-024-4246-2","DOIUrl":"https://doi.org/10.1007/s11172-024-4246-2","url":null,"abstract":"<p><i>N</i>-(Iminyl)pyridinium salts are a rare and poorly explored class of pyridine derivatives. In this work, we propose a method for the synthesis of these compounds from methyl nicotinate and hydrazones of aromatic ketones. The method involves <i>N</i>-arylation of pyridine with 2,4-dinitrophenol tosylate and subsequent reaction of the arylpyridinium salt with the amino group of <i>N</i>-unsubstituted hydrazones (the Zincke reaction).</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510071","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
Highly efficient cobalt-promoted V2O5/SiO2 catalyst for the oxidation of volatile organic compounds by ozone 臭氧氧化挥发性有机化合物的高效钴促进 V2O5/SiO2 催化剂
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4236-4
D. A. Bokarev, S. A. Kanaev, G. O. Bragina, A. E. Vaulina, G. N. Baeva, A. Yu. Stakheev
{"title":"Highly efficient cobalt-promoted V2O5/SiO2 catalyst for the oxidation of volatile organic compounds by ozone","authors":"D. A. Bokarev, S. A. Kanaev, G. O. Bragina, A. E. Vaulina, G. N. Baeva, A. Yu. Stakheev","doi":"10.1007/s11172-024-4236-4","DOIUrl":"https://doi.org/10.1007/s11172-024-4236-4","url":null,"abstract":"<p>The study demonstrates the possibility of promoting the V<sub>2</sub>O<sub>5</sub>/SiO<sub>2</sub> catalyst with a small amount of Co to increase its activity in the ozone-assisted catalytic oxidation (OZCO) of volatile organic compounds. It was found that the conversion of <i>n</i>-C<sub>4</sub>H<sub>10</sub> over the Co-promoted V<sub>2</sub>O<sub>5</sub>/SiO<sub>2</sub> catalyst (0.5% of Co w/w) at 50–100 °C significantly increases compared to that found over the reference catalysts Co<sub>3</sub>O<sub>4</sub>/SiO<sub>2</sub> and V<sub>2</sub>O<sub>5</sub>/SiO<sub>2</sub>. This is achieved by increasing the rate of O<sub>3</sub> decomposition at Co sites, which enhances the formation of reactive atomic oxygen species O*, and subsequent acceleration of the OZCO process. High efficiency of ozone consumption in the OZCO of <i>n</i>-C<sub>4</sub>H<sub>10</sub> over the Co-promoted V<sub>2</sub>O<sub>5</sub>/SiO<sub>2</sub> catalyst is due to the involvement of molecular oxygen in the oxidation reaction and to minimization of undesired recombination of the O* species.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510083","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 N-heterocyclic analogs of natural muricadienin — promising antitumor agents 合成天然花翠素的 N-杂环类似物--有望成为抗肿瘤药物
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4259-x
R. A. Tuktarova, L. U. Dzhemileva, U. M. Dzhemilev, V. A. D’yakonov
{"title":"Synthesis of N-heterocyclic analogs of natural muricadienin — promising antitumor agents","authors":"R. A. Tuktarova, L. U. Dzhemileva, U. M. Dzhemilev, V. A. D’yakonov","doi":"10.1007/s11172-024-4259-x","DOIUrl":"https://doi.org/10.1007/s11172-024-4259-x","url":null,"abstract":"<p>A series of <i>N</i>-heterocyclic analogs of muricadienin, a precursor of various acetogenins, were synthesized, and their biological activity was studied. It was revealed that the linking group between the <i>N</i>-methylpyrazole/imidazole part and the hydrophobic alkadienyl chain affects the ability of these compounds to induce apoptosis and cause cell cycle arrest. Compound <b>3b</b> showed the highest cytotoxic activity.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510123","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
Stannylenes based on alkyl- and aryl-substituted diethylenetriamines: synthesis, structure, and catalytic activity 基于烷基和芳基取代的二乙烯三胺的苯并芘：合成、结构和催化活性
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4237-3
M. U. Agaeva, B. N. Mankaev, K. A. Lyssenko, M. P. Egorov, S. S. Karlov
{"title":"Stannylenes based on alkyl- and aryl-substituted diethylenetriamines: synthesis, structure, and catalytic activity","authors":"M. U. Agaeva, B. N. Mankaev, K. A. Lyssenko, M. P. Egorov, S. S. Karlov","doi":"10.1007/s11172-024-4237-3","DOIUrl":"https://doi.org/10.1007/s11172-024-4237-3","url":null,"abstract":"<p>The reaction of 1,4,7-trisubstituted 1,4,7-triazaheptane derivatives RN(CH<sub>2</sub>CH<sub>2</sub>NHR′)<sub>2</sub> with one equivalent of Lappert’s stannylene Sn[N(SiMe<sub>3</sub>)<sub>2</sub>]<sub>2</sub> afforded the corresponding stannylenes RN(CH<sub>2</sub>CH<sub>2</sub>NR)<sub>2</sub>Sn (R′ = Bn, R = Et (<b>1h</b>), Bn (<b>1i</b>); R′ = Et, R = Et (<b>1j</b>), Bn (<b>1k);</b> R′ = Ph, R = Et (<b>1l</b>), Bu<sup>t</sup> (<b>1m</b>)) in satisfactory yields. According to the <sup>1</sup>H, <sup>13</sup>C (for <b>1h—m</b>), and <sup>119</sup>Sn (for <b>1i,k—m</b>) NMR data and the X-ray diffraction data (for stannylenes <b>1h—m</b> are monomeric; the coordination number of the tin atom is 3. Stannylenes <b>1h—m</b> were tested as initiators for the <i>ε</i>-caprolactone polymerization. The highest activity was shown by derivatives <b>1l,m</b> containing phenyl groups at the terminal nitrogen atoms of the ligand. Stannylenes <b>1h—k</b> containing ethyl and benzyl substituents are less active in the ring-opening polymerization of <i>ε</i>-caprolactone.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141530046","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
Nitro-substituted 2-aryl-[1,2,4]triazolo[1,5-a]azines in the reactions with C-nucleophiles 硝基取代的 2-芳基-[1,2,4]三唑并[1,5-a]氮杂与 C-亲核物的反应
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4251-5
M. A. Bastrakov, A. A. Kruchinin, S. A. Kolyadina, A. M. Starosotnikov
{"title":"Nitro-substituted 2-aryl-[1,2,4]triazolo[1,5-a]azines in the reactions with C-nucleophiles","authors":"M. A. Bastrakov, A. A. Kruchinin, S. A. Kolyadina, A. M. Starosotnikov","doi":"10.1007/s11172-024-4251-5","DOIUrl":"https://doi.org/10.1007/s11172-024-4251-5","url":null,"abstract":"<p>Synthesis of nitro-substituted [1,2,4]triazolo[1,5-<i>a</i>]pyrimidines based on oxidative cyclization of the corresponding nitropyrimidinyl hydrazones of aromatic aldehydes was developed. The reactions of 2-aryl-6-nitro-[1,2,4]triazolo[1,5-<i>a</i>]pyrimidines and their structural analogs (2-aryl-6,8-dinitro-[1,2,4]triazolo[1,5-<i>a</i>]pyridines) with different C-nucleophiles were studied. Nucleophilic addition to the pyridine and pyrimidine rings carried out under mild base-free conditions gave new stable 1.5-dihydro-[1,2,4]triazolo [1,5-<i>a</i>]-pyridines and 1.5-dihydro-[1,2,4]triazolo[1,5-<i>a</i>]pyrimidines in the yields up to 94%.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510082","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 5-oxo-1-[4-(aminosulfonyl)phenyl]pyrrolidine-3-carboxylic acids 合成 5-氧代-1-[4-(氨基磺酰基)苯基]吡咯烷-3-羧酸
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4243-5
S. A. Serkov, N. V. Sigay, N. N. Kostikova, A. P. Tyurin, N. G. Kolotyrkina, G. A. Gazieva
{"title":"Synthesis of 5-oxo-1-[4-(aminosulfonyl)phenyl]pyrrolidine-3-carboxylic acids","authors":"S. A. Serkov, N. V. Sigay, N. N. Kostikova, A. P. Tyurin, N. G. Kolotyrkina, G. A. Gazieva","doi":"10.1007/s11172-024-4243-5","DOIUrl":"https://doi.org/10.1007/s11172-024-4243-5","url":null,"abstract":"<p>A series of new 1-[4-(aminosulfonyl)phenyl]-5-oxopyrrolidine-3-carboxylic acids were synthesized by the solvent-free condensation of 4-aminobenzenesulfonamides with itaconic acid at 140–165 °C. The synthesized compounds were examined for antimicrobial activity.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510069","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
Pathways of reactions of 2-arylcyclopropane-1,1-dicarboxylates with monosubstituted cycloheptatrienes under the action of GaCl3 2- 芳基环丙烷-1,1-二羧酸盐与单取代环庚三烯在三氯化镓作用下的反应途径
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4239-1
D. D. Borisov, A. A. Ershova, D. N. Platonov, R. A. Novikov, Yu. V. Tomilov
{"title":"Pathways of reactions of 2-arylcyclopropane-1,1-dicarboxylates with monosubstituted cycloheptatrienes under the action of GaCl3","authors":"D. D. Borisov, A. A. Ershova, D. N. Platonov, R. A. Novikov, Yu. V. Tomilov","doi":"10.1007/s11172-024-4239-1","DOIUrl":"https://doi.org/10.1007/s11172-024-4239-1","url":null,"abstract":"<p>The reaction of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) with the unsaturated cyclohepta-2,4,6-triene-1-carboxylate system under the action of GaCl<sub>3</sub> proceeds with a contraction of the seven-membered cycle and formally corresponds to the [2+4] or [3+2] cycloaddition of 1,2- or 1,3-zwitterionic intermediates generated from ACDCs to the double bonds of the norcaradiene structure. On the contrary, cycloheptatrienes with donor substituents practically do not form cycloaddition products in reactions with 1,2-zwitterionic intermediates, but undergo dehydrogenation and significant oligomerization. Methyl- and phenylcycloheptatriene turned out to be rather good precursors of hydride ions, which resulted in the formation of (2-phenylethyl)malonate, while 7-methoxycycloheptatriene predominantly transforms the 1,2-zwitterion open form to the initial ACDC.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510064","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 spin-labeled bispidines 自旋标记二叉膦的合成
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-06-21 DOI: 10.1007/s11172-024-4241-7
A. M. Zakirov, A. V. Medved’ko, I. I. Troshin, E. V. Tretyakov, S. Z. Vatsadze
{"title":"Synthesis of spin-labeled bispidines","authors":"A. M. Zakirov, A. V. Medved’ko, I. I. Troshin, E. V. Tretyakov, S. Z. Vatsadze","doi":"10.1007/s11172-024-4241-7","DOIUrl":"https://doi.org/10.1007/s11172-024-4241-7","url":null,"abstract":"<p>Conjugates of bispidines and free radicals of the (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl type were synthesized for the first time. The conjugates were obtained by the alkylation reaction of NH-bispidines with electrophilic chloro derivatives containing a free radical. The structure of the latter was established by X-ray diffraction analysis. The products obtained were characterized by IR spectroscopy, ESR spectroscopy, and high-resolution mass spectrometry.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141510068","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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