Pub Date : 2024-08-30DOI: 10.1134/s1070428024060186
M. Pradeep, M. Vishnuvardhan, A. Ganesh, Gangadhar Thalari
Abstract
A novel series of pyrrolidinylquinoline–imidazolyl-1,2,3-triazole hybrids were synthesised starting from 2-(pyrrolidine-1-yl)quinoline-3-carbaldehyde. The aldehyde was reacted with o-phenylenediamine to produce benzimidazole derivative which was alkylated with propargyl bromide and then subjected to copper-catalyzed azide–alkyne cycloaddition to afford the desired 1,2,3-triazole derivatives. The cycloaddition step was performed under both traditional stirring and microwave irradiation. All synthesized triazole derivatives were screened for their in vitro antimicrobial activity against various bacterial and fungal pathogens. The majority of the synthesized compounds demonstrated moderate to good inhibition zones compared to the standard drugs.
{"title":"Green Synthesis and Antimicrobial Activity of 3-{1-[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzimidazol-2-yl}-2-(pyrrolidin-1-yl)quinoline Derivatives","authors":"M. Pradeep, M. Vishnuvardhan, A. Ganesh, Gangadhar Thalari","doi":"10.1134/s1070428024060186","DOIUrl":"https://doi.org/10.1134/s1070428024060186","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A novel series of pyrrolidinylquinoline–imidazolyl-1,2,3-triazole hybrids were synthesised starting from 2-(pyrrolidine-1-yl)quinoline-3-carbaldehyde. The aldehyde was reacted with <i>o</i>-phenylenediamine to produce benzimidazole derivative which was alkylated with propargyl bromide and then subjected to copper-catalyzed azide–alkyne cycloaddition to afford the desired 1,2,3-triazole derivatives. The cycloaddition step was performed under both traditional stirring and microwave irradiation. All synthesized triazole derivatives were screened for their in vitro antimicrobial activity against various bacterial and fungal pathogens. The majority of the synthesized compounds demonstrated moderate to good inhibition zones compared to the standard drugs.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227528","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060083
L. S. Khasanova, V. A. Egorov, M. F. Abdullin, F. A. Gimalova
Abstract
The reaction of 5-allenyl-2,3,5-trichlorocyclopentenone with glycine, L-methionine, L-leucine, and L-tyrosine methyl esters gave the corresponding AdNE adducts, and the subsequent oxidative cleavage of the allene fragment afforded new 4-carboxymethylidene derivatives.
{"title":"New Cross-Conjugated Chlorocyclopentenone Derivatives Containing an Amino Acid Fragment at C3","authors":"L. S. Khasanova, V. A. Egorov, M. F. Abdullin, F. A. Gimalova","doi":"10.1134/s1070428024060083","DOIUrl":"https://doi.org/10.1134/s1070428024060083","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>The reaction of 5-allenyl-2,3,5-trichlorocyclopentenone with glycine, L-methionine, L-leucine, and L-tyrosine methyl esters gave the corresponding Ad<sub>N</sub>E adducts, and the subsequent oxidative cleavage of the allene fragment afforded new 4-carboxymethylidene derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222333","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060137
I. O. Gudkova, E. A. Sorokina, E. A. Zaborin, M. S. Polinskaya, O. V. Borshchev, S. A. Ponomarenko
Abstract
Mono- and dioctyl-substituted benzo[b]benzo[4,5]thieno[2,3-d]thiophenes C8-BTBT and C8-BTBT-C8 that are widely used as organic semiconductors in the manufacture of various organic electronic devices have been synthesized in two steps, by Friedel–Crafts acylation of benzo[b]benzo[4,5]thieno[2,3-d]thiophene (BTBT) and subsequent reduction of the ketone group(s). Taking into account that the limiting stage in the synthesis of such compounds is the reduction stage, different methods for the reduction acyl-substituted BTBT derivatives have been studied and probable reduction mechanisms have been proposed. The best results in the keto group reduction stage have been obtained with the use of hydrazine hydrate as reducing agent.
{"title":"Peculiar Features of the Reduction of Keto Group in the Synthesis of Mono- and Dialkyl-Substituted Benzo[b]benzo[4,5]thieno[2,3-d]thiophene","authors":"I. O. Gudkova, E. A. Sorokina, E. A. Zaborin, M. S. Polinskaya, O. V. Borshchev, S. A. Ponomarenko","doi":"10.1134/s1070428024060137","DOIUrl":"https://doi.org/10.1134/s1070428024060137","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Mono- and dioctyl-substituted benzo[<i>b</i>]benzo[4,5]thieno[2,3-<i>d</i>]thiophenes <b>C8-BTBT</b> and <b>C8-BTBT-C8</b> that are widely used as organic semiconductors in the manufacture of various organic electronic devices have been synthesized in two steps, by Friedel–Crafts acylation of benzo[<i>b</i>]benzo[4,5]thieno[2,3-<i>d</i>]thiophene (BTBT) and subsequent reduction of the ketone group(s). Taking into account that the limiting stage in the synthesis of such compounds is the reduction stage, different methods for the reduction acyl-substituted BTBT derivatives have been studied and probable reduction mechanisms have been proposed. The best results in the keto group reduction stage have been obtained with the use of hydrazine hydrate as reducing agent.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222336","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060058
V. R. Sinyakov, T. V. Mezhenkova, V. M. Karpov, Ya. V. Zonov
Abstract
The reaction of perfluorotetralin with zinc in DMF, followed by treatment with water, gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2′-binaphthalene, and octafluoronaphthalene. Under similar conditions, perfluoro-1-ethyltetralin was converted into a mixture of 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes, perfluoro-6-methyltetralin gave rise to 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene, and perfluoro-1-methylnaphthalene was obtained from perfluoro-4-methyl-1,2-dihydronaphthalene. Perfluoro-1-ethyltetralin reacted with bromine-activated zinc in DMF to produce a mixture containing (perfluoro-4-ethylnaphthalen-1-yl)zinc bromide which was converted to 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene by the action of water, while its reaction with CuCl2 afforded perfluoro-4,4′-diethyl-1,1′-binaphthalene.
{"title":"Defluorination and Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-dihydronaphthalene in the System Zn–DMF. Synthesis of Perfluoro-1-ethyl- and -1-methylnaphthalenes","authors":"V. R. Sinyakov, T. V. Mezhenkova, V. M. Karpov, Ya. V. Zonov","doi":"10.1134/s1070428024060058","DOIUrl":"https://doi.org/10.1134/s1070428024060058","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>The reaction of perfluorotetralin with zinc in DMF, followed by treatment with water, gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2′-binaphthalene, and octafluoronaphthalene. Under similar conditions, perfluoro-1-ethyltetralin was converted into a mixture of 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes, perfluoro-6-methyltetralin gave rise to 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene, and perfluoro-1-methylnaphthalene was obtained from perfluoro-4-methyl-1,2-dihydronaphthalene. Perfluoro-1-ethyltetralin reacted with bromine-activated zinc in DMF to produce a mixture containing (perfluoro-4-ethylnaphthalen-1-yl)zinc bromide which was converted to 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene by the action of water, while its reaction with CuCl<sub>2</sub> afforded perfluoro-4,4′-diethyl-1,1′-binaphthalene.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227508","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060034
T. A. Kulahava, V. A. Shumski, I. V. Mineyeva
Abstract
Modification of 2-acetyl-3H-benzo[f]chromen-3-one and 2-[(2E)-3-phenylprop-2-enoyl]-3H-benzo[f]chromen-3-one has been performed for the first time via the reaction with indole. The resulting benzo[f]coumarins have been found to exhibit antioxidant properties in model systems: they react with hydrogen peroxide and sodium hypochlorite and regulate redox state of rat C6 glioma cells, which is reflected in reduced concentration of intracellular hydrogen peroxide and increased level of reduced glutathione. The synthesized compounds in the presence of exogenous hydrogen peroxide exert a protective effect on the cells, acting as antioxidants and restoring the redox balance. 2-[3-(1H-Indol-3-yl)-3-phenylpropanoyl]-3H-benzo[f]khromen-3-one at a micromolar concentrations inhibited the rat C6 glioma cell proliferation by 25–35%.
{"title":"Synthesis of New Indole-Containing Benzo[f]coumarin Derivatives and Their Effect on the Proliferation and Redox State of Rat C6 Glioma Cells","authors":"T. A. Kulahava, V. A. Shumski, I. V. Mineyeva","doi":"10.1134/s1070428024060034","DOIUrl":"https://doi.org/10.1134/s1070428024060034","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Modification of 2-acetyl-3<i>H</i>-benzo[<i>f</i>]chromen-3-one and 2-[(2<i>E</i>)-3-phenylprop-2-enoyl]-3<i>H</i>-benzo[<i>f</i>]chromen-3-one has been performed for the first time via the reaction with indole. The resulting benzo[<i>f</i>]coumarins have been found to exhibit antioxidant properties in model systems: they react with hydrogen peroxide and sodium hypochlorite and regulate redox state of rat C6 glioma cells, which is reflected in reduced concentration of intracellular hydrogen peroxide and increased level of reduced glutathione. The synthesized compounds in the presence of exogenous hydrogen peroxide exert a protective effect on the cells, acting as antioxidants and restoring the redox balance. 2-[3-(1<i>H</i>-Indol-3-yl)-3-phenylpropanoyl]-3<i>H</i>-benzo[<i>f</i>]khromen-3-one at a micromolar concentrations inhibited the rat C6 glioma cell proliferation by 25–35%.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222310","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060204
D. A. Lomov
Abstract
The reaction of ethyl pyridine-2-ylcarbamate with phenacyl bromides in acetonitrile gave 2-aryl-1-(ethoxycarbonyl)-2-hydroxy-2-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridine-4-ium bromides which were converted into 2-arylimidazo[1,2-a]pyridines by heating in acetic anhydride, followed by treatment with potassium carbonate.
{"title":"Quaternization of Ethyl Pyridin-2-ylcarbamate with Phenacyl Bromides","authors":"D. A. Lomov","doi":"10.1134/s1070428024060204","DOIUrl":"https://doi.org/10.1134/s1070428024060204","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>The reaction of ethyl pyridine-2-ylcarbamate with phenacyl bromides in acetonitrile gave 2-aryl-1-(ethoxycarbonyl)-2-hydroxy-2-phenyl-2,3-dihydro-1<i>H</i>-imidazo[1,2-<i>a</i>]pyridine-4-ium bromides which were converted into 2-arylimidazo[1,2-<i>a</i>]pyridines by heating in acetic anhydride, followed by treatment with potassium carbonate.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227510","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060010
L. P. Yunnikova, O. V. Pshenitsyna
Abstract
The review summarizes literature data on new nucleophilic functionalization reactions of tropylium salts with heterocyclic amines and monocarboxylic acid amides and hydrazides over the past decade.
摘要 综述了过去十年中有关托品鎓盐与杂环胺和单羧酸酰胺及酰肼的新亲核功能化反应的文献数据。
{"title":"Nucleophilic Functionalization of Tropylium Salts with Heterocyclic Amines and Carboxylic Acid Amides and Hydrazides","authors":"L. P. Yunnikova, O. V. Pshenitsyna","doi":"10.1134/s1070428024060010","DOIUrl":"https://doi.org/10.1134/s1070428024060010","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>The review summarizes literature data on new nucleophilic functionalization reactions of tropylium salts with heterocyclic amines and monocarboxylic acid amides and hydrazides over the past decade.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227505","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060150
Y. Bouchebcheb, D. Fedaoui, A. Alem, M. Liacha
Abstract
A new series of Schiff bases have been prepared by the condensation between 3-methyl-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde and primary aromatic amines using an eco-friendly method that employs the ionic liquid triethylammonium acetate [TEAA] as a solvent and catalyst at 80°C under ultrasonic irradiation. This protocol has a number of benefits, including short reaction times, direct isolation of the pure product, and high yield. The structures of the newly synthesized derivatives were established on the basis of IR, 1H NMR, and 13C NMR spectroscopic techniques (including two-dimensional 1H–13C HSQC and 1H–13C HMBC experiments) and elemental analysis. A DFT theoretical study was carried out for the synthesized molecules in the gas phase using the B3LYP method with 6-311G(d,p) basis set; the HUMO and LUMO energies were calculated for the optimized geometries, which showed that compound 4e is the most stable with an energy gap of 4.05585 eV, as presented by the DOS spectrum. The reactivity of the compounds was studied by calculating some global reactivity descriptors, revealing that compound 4b is the most chemically reactive. In addition, molecular electrostatic potentials (MEP) was studied for the reaction centers of the synthesized compounds.
{"title":"Ultrasound-Assisted Synthesis and DFT Studies of Novel Schiff Bases Derived from 3-Methyl-1,3-benzothiazol-2(3H)-one in an Ionic Liquid Medium","authors":"Y. Bouchebcheb, D. Fedaoui, A. Alem, M. Liacha","doi":"10.1134/s1070428024060150","DOIUrl":"https://doi.org/10.1134/s1070428024060150","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A new series of Schiff bases have been prepared by the condensation between 3-methyl-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde and primary aromatic amines using an eco-friendly method that employs the ionic liquid triethylammonium acetate [TEAA] as a solvent and catalyst at 80°C under ultrasonic irradiation. This protocol has a number of benefits, including short reaction times, direct isolation of the pure product, and high yield. The structures of the newly synthesized derivatives were established on the basis of IR, <sup>1</sup>H NMR, and <sup>13</sup>C NMR spectroscopic techniques (including two-dimensional <sup>1</sup>H–<sup>13</sup>C HSQC and <sup>1</sup>H–<sup>13</sup>C HMBC experiments) and elemental analysis. A DFT theoretical study was carried out for the synthesized molecules in the gas phase using the B3LYP method with 6-311G(<i>d</i>,<i>p</i>) basis set; the HUMO and LUMO energies were calculated for the optimized geometries, which showed that compound <b>4e</b> is the most stable with an energy gap of 4.05585 eV, as presented by the DOS spectrum. The reactivity of the compounds was studied by calculating some global reactivity descriptors, revealing that compound <b>4b</b> is the most chemically reactive. In addition, molecular electrostatic potentials (MEP) was studied for the reaction centers of the synthesized compounds.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222332","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060174
K. Ramya, Seena Chakko, V. S. Shinu, S. Arun
Abstract
An efficient, mild, and green one-pot multicomponent synthetic approach has been proposed for the synthesis of β-amido carbonyl scaffolds via coupling of aromatic aldehydes, enolizable ketones, and acetonitrile in the presence of acetyl chloride and ammonium chloride as a metal-free highly effective catalyst. The developed approach provides a novel cost-effective and environmentally friendly route to access highly functionalized structural scaffolds in in good to excellent yields and requires less operational skill and conditions.
{"title":"Expanding the Scope of Metal-Free Catalytic Approach for the Green One-Pot Multicomponent Synthesis of β-Amido Carbonyl Scaffolds","authors":"K. Ramya, Seena Chakko, V. S. Shinu, S. Arun","doi":"10.1134/s1070428024060174","DOIUrl":"https://doi.org/10.1134/s1070428024060174","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>An efficient, mild, and green one-pot multicomponent synthetic approach has been proposed for the synthesis of β-amido carbonyl scaffolds via coupling of aromatic aldehydes, enolizable ketones, and acetonitrile in the presence of acetyl chloride and ammonium chloride as a metal-free highly effective catalyst. The developed approach provides a novel cost-effective and environmentally friendly route to access highly functionalized structural scaffolds in in good to excellent yields and requires less operational skill and conditions.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222335","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}
Pub Date : 2024-08-30DOI: 10.1134/s1070428024060095
K. E. Shepelenko, I. G. Gnatiuk, V. M. Chernyshev
Abstract
Unusual direction of the C–H arylation of 2-(het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with (het)aryl halides under catalysis by ruthenium(II) complexes has been revealed. The reaction involved activation of the C7–H bond rather than the Cα–H bond of the (het)aryl substituent at C2 of the triazolopyrimidine core. The arylation of 2-substituted [1,2,4]triazolo[1,5-a]pyrimidines with (het)aryl bromides afforded a series of 7-(het)aryl derivatives in good yields.
{"title":"Ruthenium-Catalyzed Regioselective C7–H Arylation of 2-(Het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with Aryl Halides","authors":"K. E. Shepelenko, I. G. Gnatiuk, V. M. Chernyshev","doi":"10.1134/s1070428024060095","DOIUrl":"https://doi.org/10.1134/s1070428024060095","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Unusual direction of the C–H arylation of 2-(het)aryl[1,2,4]triazolo[1,5-<i>a</i>]pyrimidines with (het)aryl halides under catalysis by ruthenium(II) complexes has been revealed. The reaction involved activation of the C<sup>7</sup>–H bond rather than the C<sup>α</sup>–H bond of the (het)aryl substituent at C<sup>2</sup> of the triazolopyrimidine core. The arylation of 2-substituted [1,2,4]triazolo[1,5-<i>a</i>]pyrimidines with (het)aryl bromides afforded a series of 7-(het)aryl derivatives in good yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222313","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}
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