{"title":"Regioselective Synthesis of 3,4,5-Trisubstituted Pyrazoles from 2,3-Allenoates and a Sterically Hindered Diazo Ketone: Expanding the Scope of 1,3-Dipolar Cycloaddition","authors":"G. M. Gindullina, I. M. Sakhautdinov","doi":"10.1134/S1234567825601731","DOIUrl":"10.1134/S1234567825601731","url":null,"abstract":"<p>Novel 3,4,5-trisubstituted pyrazoles were synthesized from keto-stabilized 2,3-allenoates and a sterically hindered diazoketone (derived from α-amino-β-phenylpropionic acid) in acetonitrile under thermal conditions. The reaction occurred in a regio- and stereoselective fashion, positioning the bulky substituents in the diazoketone moiety of the resulting pyrazoles at the maximal distance from the ester group. The physical properties of the synthesized compounds were investigated.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"855 - 859"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143150","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. G. Danagulyan, L. S. Khachatryan, А. G. Danagulyan, M. Yu. Dangyan, G. A. Panosyan
{"title":"Recyclization of a Pyrimidinium Salt as a Synthetic Approach to Novel Nitrogenous Heterocycles","authors":"G. G. Danagulyan, L. S. Khachatryan, А. G. Danagulyan, M. Yu. Dangyan, G. A. Panosyan","doi":"10.1134/S1234567825601469","DOIUrl":"10.1134/S1234567825601469","url":null,"abstract":"<p>The recyclization of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidin-1-ium iodide under the action of ethylhydrazine and (4,6-dimethylpyrimidin-2-yl)acetic acid hydrazide, 1-ethyl-3-(ethoxycarbonyl)methyl-5-methyl-1,2,4-triazole and 5,7-dimethyl-3-(ethoxycarbonyl)-2-(4',6'-dimethylyrimidin- 2'-yl-)methylpyrazolo[1,5-<i>a</i>]pyrimidine were synthesized, respectively. Alkylation of 1-ethyl-3-ethoxycarbonylmethyl-5-methyl-1,2,4-triazole with various alkyl iodides yielded the corresponding <i>N</i>-alkyltriazolium salts, and reactions of triazolylacetic acid esters yielded their hydrazides. Based on the nuclear Overhauser effect (NOE), it was clearly demonstrated that alkylation occurs at the N-4 nitrogen atom of the triazole ring.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"974 - 980"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143153","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}
Z. F. Nuriakhmetova, S. A. Torosyan, F. A. Gimalova, M. S. Miftakhov
{"title":"Synthesis of New 1,2,3-Triazole Derivatives of Methyl 4-Propargylthieno[3,2-b]pyrrole-5-carboxylate","authors":"Z. F. Nuriakhmetova, S. A. Torosyan, F. A. Gimalova, M. S. Miftakhov","doi":"10.1134/S123456782560138X","DOIUrl":"10.1134/S123456782560138X","url":null,"abstract":"<p>New 1,2,3-triazole derivatives of methyl 4-(2-propyn-1-yl)-1<i>H</i>-thieno[3.2-<i>b</i>]pyrrole-5-carboxylate, which have a methylene bridge between the heterocyclic units.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"860 - 863"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143162","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":"One-Pot Synthesis of 3,4-Dihydropyrimidino[2,1-a]isoindol-6(2H)-one","authors":"G. S. Martyanov, M. A. Barabanov, A. V. Pestov","doi":"10.1134/S1234567825601494","DOIUrl":"10.1134/S1234567825601494","url":null,"abstract":"<p>A one-pot synthesis of 3,4-dihydropyrimidino[2,1-<i>a</i>]isoindol-6(2<i>H</i>)-one, an analog of the promising anticancer drug batracylin, involving the acylation of 1,3-diaminopropane with phthalic anhydride followed by cyclocondensation under heating in toluene or <i>o</i>-xylene, was developed. The highest yield of the target isoindolone of 76% was obtained by adding 1,3-diaminopropane to phthalic anhydride in toluene, while when the order of reagent addition was reversed, the yield decreased to 60%. The reaction occurred stepwise through the formation of 2-[(3-aminopropyl)carbamoyl)]benzoic acid and its subsequent conversion to isoindolone under heating in a yield of 68%.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"831 - 837"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145142917","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}
L. V. Klyba, E. R. Sanzheeva, N. A. Nedolya, O. A. Tarasova
{"title":"Mass Spectra of New Heterocycles: XXIX. Study of 2-(Alkylsulfanyl)quinolines by Electron Ionization Mass Spectrometry","authors":"L. V. Klyba, E. R. Sanzheeva, N. A. Nedolya, O. A. Tarasova","doi":"10.1134/S1234567825600816","DOIUrl":"10.1134/S1234567825600816","url":null,"abstract":"<p>The behavior of a representative series of previously unknown 2-(alkylsulfanyl)quinolines, prepared from aryl isothiocyanates, allene or acetylene carbanions, and methyl iodide, under electron ionization (70 eV) have been studied for the first time. The studied compounds all form stable molecular ions clearly detected in the mass spectra and have similar fragmentation patterns, including the formation of [<i>M</i> – H]<sup>+</sup>, [<i>M</i> – Me]<sup>+</sup>, and [<i>M</i> – HS]<sup>+</sup> ions. Fragmentation is most affected by the nature of the substituents in positions 3 and 4 of the quinoline pyridine ring. The molecular ion of 4-methyl-2-(methylsulfanyl)-3-(1<i>H</i>-pyrrol-1-yl)quinolines undergoes rearrangement, which involves either the sulfur atom or the carbon atom of the 4-methyl substituent in the heteroring. The fragmentation pathways of the fragment ions of the studied 2-(alkylsulfanyl)quinolines are proposed based on an analysis of the daughter ion mass spectra.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"800 - 812"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143163","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. V. Velikorodov, E. N. Kutlalieva, E. A. Shustova, S. B. Nosachev
{"title":"Synthesis of New Functionally Substituted Pyrazoles and Indoles from Acetophenones with a Carbamate Moiety","authors":"A. V. Velikorodov, E. N. Kutlalieva, E. A. Shustova, S. B. Nosachev","doi":"10.1134/S1234567825601378","DOIUrl":"10.1134/S1234567825601378","url":null,"abstract":"<p>The condensation of acetophenones containing a carbamate moiety with phenylhydrazine in ethanol was used to obtain the corresponding phenylhydrazones, which were further converted into methyl <i>N</i>-[2(3,4)-(4-formyl-1-phenyl-1<i>H</i>-pyrazol-3-yl)phenyl]carbamates in yields of 79–83% via the Vilsmeier–Haack reaction. Refluxing methyl <i>N</i>-[4-(4-formyl-1-phenyl-1<i>H</i>-pyrazol-3-yl)phenyl]carbamate with barbituric and thiobarbituric acids in ethanol in the presence of triethylamine gave methyl <i>N</i>-[4-(1-phenyl-4-{[2,4,6-trioxotetrahydro-5(2<i>H</i>)-pyrimidinylidene]methyl}-1<i>H</i>-pyrazol-3-yl)phenyl]carbamate and methyl <i>N</i>-[4-(4-{[4,6-dioxo-2-thioxotetrahydro-5(2<i>H</i>)-pyrimidinylidene]methyl}-1-phenyl-1<i>H</i>-pyrazol-3-yl)phenyl]carbamate in yields of 50–54%. The three-component condensation of methyl <i>N</i>-[4-(4-formyl-1-phenyl-1<i>H</i>-pyrazol-3-yl)phenyl]carbamate with thiourea and ethyl acetoacetate or ethyl cyanoacetate under reflux in ethanol afforded ethyl 4-(3-{4-[(methoxycarbonyl)amino]phenyl}-1-phenyl-1<i>H</i>-pyrazol-4-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate and methyl <i>N</i>-{4-[4-(6-oxo-2-thioxo-5-cyano-1,2,3,6-tetrahydro-4-pyrimidinyl)-1-phenyl-1<i>H</i>-pyrazol-3-yl]phenyl}carbamate in yields of 61 and 75% yields, respectively. Treatment of the synthesized phenylhydrazones with boron trifluoride etherate in glacial acetic acid under heating resulted in the formation of methyl <i>N</i>-[2(3,4)-(1<i>H</i>-indol-2-yl)phenyl]carbamates in yields of 84–86%. 3-Nitroso-, 3-amino-, and 3-methoxycarbonylamino derivatives of methyl <i>N</i>-[4-(1<i>H</i>-indol-2-yl)phenyl]carbamate were also prepared.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"838 - 846"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143166","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, I. G. Abramov, V. V. Aleksandriiskii
{"title":"Synthesis of Heterocycles Based on 4,5-Dichlorophthalonitrile","authors":"V. L. Baklagin, V. V. Bukhalin, I. G. Abramov, V. V. Aleksandriiskii","doi":"10.1134/S1234567825600932","DOIUrl":"10.1134/S1234567825600932","url":null,"abstract":"<p>The <i>S</i><sub>N</sub>Ar reaction of 4,5-dichlorophthalonitrile with various bifunctional nucleophiles was carried out in anhydrous DMF in the presence of K<sub>2</sub>CO<sub>3</sub> as a deprotonating agent. It was shown that 4,5-dichlorophthalonitrile can be successfully employed in the synthesis of heterocyclic compounds; however, in some cases, these reactions may either give product mixtures or result in an unexpected rearrangement.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"813 - 820"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143156","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}
Shu-Tong Han, Cong Qi, Zhao-Yuan Zhang, Wei Hong, Ran He, Peng-Hong Hu, Yao-Yao Cao, Yuan-Fen Zhai, Da-Hua Shi
{"title":"Synthesis, Characterization, and Anticancer Activity of 2-Aminothiazole Derivatives","authors":"Shu-Tong Han, Cong Qi, Zhao-Yuan Zhang, Wei Hong, Ran He, Peng-Hong Hu, Yao-Yao Cao, Yuan-Fen Zhai, Da-Hua Shi","doi":"10.1134/S1234567825600026","DOIUrl":"10.1134/S1234567825600026","url":null,"abstract":"<p>Eight novel 2-[(substituted)acetamido]thiazole-4-carboxylates were designed and synthesized as potential anticancer agents. The synthesized compounds were tested for in vitro cytotoxic activity against Panc-1 cells by the MTT assay and showed significant inhibition of cell proliferation. At 90 μM, ethyl 2-[2-(dibutylamino)acetamido]- and 2-[2-(4-methylpiperidin-1-yl)acetamidothiazole-carboxylates inhibited proliferation by > 50%, with the former demonstrating a particularly strong potency (IC<sub>50</sub> = 43.08 μM<b>)</b>. Further experiments showed the ethyl 2-(2-(dibutylamino)acetamido)thiazole-4-carboxylate also markedly inhibited Panc-1 cell migration, invasion, and adhesion, which positions this compound as a promising candidate for anticancer drug development.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"881 - 891"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143158","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":"Green Synthesis of Novel Bis(1,2,3,4-tetrahydropyrimidines) and Impact of Rigid Linkers on Their In Vitro ACE Inhibitory and Antimicrobial Activities","authors":"S. K. Bhatia, V. Samdhian, B. Kaur","doi":"10.1134/S1234567824604923","DOIUrl":"10.1134/S1234567824604923","url":null,"abstract":"<p>This study focuses on the convergent one-pot, multicomponent greener synthesis of novel bis(1,2,3,4-tetrahydropyrimidines) via the renowned Biginelli reaction. Dialdehydes with five different rigid linkers were employed as key precursors for the target compounds. All reactions were performed under microwave irradiation and were complete within a few minutes. The target compounds were isolated with remarkable yields and high purity and characterized using up-to-date spectroscopic methods. All the synthesized compounds were tested for in vitro ACE inhibitory activity, as well as for antimicrobial activity against two Gram-positive and two Gram-negative bacterial strains and antifungal activity against <i>Aspergillus flavus</i> and <i>Aspergillus niger</i>. The results showed that the choice of linkers and the presence of sulfur or oxygen at the C<sup>2</sup> position of the pyrimidine rings strongly affect the biological activity of the compounds. The highest ACE inhibitory activity with an IC<sub>50</sub> value of 7.29 μg/mL was revealed in bis(1,2,3,4-tetrahydro-1,3-pyrimidine-2-thione) with an alkyne linker, and the same compound and its structural analog containing 1,3-pyrimidin-2-one moieties were identified as the most potent antibacterial agents.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"931 - 940"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143151","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 Principal Building Blocks of Amphidinolides of the G and H Families","authors":"I. V. Mineyeva","doi":"10.1134/S1070428025600809","DOIUrl":"10.1134/S1070428025600809","url":null,"abstract":"<p>Unsaturated lactones, (6<i>R</i>)- and (6<i>S</i>)-6-[(2<i>R</i>)-1,4-dioxaspiro[4.5]dec-2-yl]-4-methyl-5,6-dihydro-2<i>H</i>-pyran-2-ones, have been synthesized by diastereoselective allylation of (<i>R</i>)-2,3-<i>O</i>-cyclohexylideneglyceraldehyde with methyl 3-(bromomethyl)but-3-enoate and its allylstannyl derivative. These lactones have been subjected to highly diastereoselective reduction and utilized in a new retrosynthetic scheme for obtaining C<sup>5</sup>–C<sup>14</sup>, C<sup>15</sup>–C<sup>19</sup>, and C<sup>20</sup>–C<sup>26</sup> building blocks of amphidinolide G and H families.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"587 - 601"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143575","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}