{"title":"Microwave-Assisted Synthesis and Characterization of Calix[4]resorcinarenes","authors":"P. H. Kanaiya, V. K. Jain","doi":"10.1134/S107042802410018X","DOIUrl":"10.1134/S107042802410018X","url":null,"abstract":"<p>Microwave irradiation was used to promote the cyclocondensation of certain aldehydes and resorcinol, resulting in a sustainable synthesis of calix[4]resorcinarenes. This environmentally conscious technology possesses numerous attractive characteristics, including high productivity, short reaction time, and straightforward workup protocol. The structures of all calix[4]resorcinarenes were verified using a range of physicochemical techniques, including elemental analysis, FT-IR, <sup>1</sup>H NMR, and mass spectrometry.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2014 - 2019"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858722","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, Crystal Structure, and Antibacterial Activity of N-(2-Chlorobenzyl)-3-methylbut-2-enamide","authors":"W. J. Hu, Y. Q. Liu, J. Y. Yu","doi":"10.1134/S1070428024100191","DOIUrl":"10.1134/S1070428024100191","url":null,"abstract":"<p><i>N</i>-(2-Сhlorobenzyl)-3-methylbut-2-enamide was synthesized, and its structure was determined by single crystal X-ray diffraction and other spectroscopic methods. The compound crystallized in <i>P</i>-1 space group of the triclinic crystal system with the following unit cell parameters: <i>a</i> = 8.8767(5), <i>b</i> = 10.2535(6), <i>c</i> = 13.8768(7) Å; α = 98.608(4)°, β = 103.920(4)°, γ = 98.298(4)°; <i>Z</i> = 4; <i>d</i><sub>calc</sub> = 1.248 g/cm<sup>3</sup>; <i>V</i> = 1190.54(12) Å<sup>3</sup>. Preliminary antibacterial tests showed that <i>N</i>-(2-chlorobenzyl)-3-methylbut-2-enamide exhibited strong antibacterial activity against <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> with minimum inhibitory concentration (MIC) values of 0.01 and 0.02 g/mL, respectively. However, this compound has no obvious bacteriostatic effect on <i>Enterobacter aerogenes</i>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2020 - 2025"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859590","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":"A Facile and Highly Efficient One-Pot Synthesis of Symmetrical and Unsymmetrical Aldazines Using Reusable MMZHY Solid Acid Catalyst","authors":"S. Ilaamirthamani, M. Kumarraja","doi":"10.1134/S1070428024100099","DOIUrl":"10.1134/S1070428024100099","url":null,"abstract":"<p>A detailed study on one-pot synthesis of 2,3-diaza-1,3-butadiene derivatives from various aromatic aldehydes and hydrazine by using MMZ<sub>HY</sub> solid acid catalyst is reported. The role of the bifunctional nature of MMZ<sub>HY</sub> and the effect of metal ions in the catalyst are described with a supportive mechanism. Both symmetrical and unsymmetrical aldazines (hydrazone free) were prepared with excellent yields and characterized by <sup>1</sup>H and <sup>13</sup>C NMR spectra. The other advantages of the catalytic system like its easy preparation by the bottom-up method, reusability, multiporous nature which reduces diffusional limitations, easy separation, and mild reaction conditions with higher yield of products are also highlighted.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1950 - 1955"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859705","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. Hfaiedh, I. Smari, H. Marzouki, Ch. Youssef, H. Ben Ammar
{"title":"A Practical Transition Metal-Free Synthesis of Highly Substituted Thiophenes Containing a Benzoxazole Moiety and Their Antimicrobial Activity","authors":"A. Hfaiedh, I. Smari, H. Marzouki, Ch. Youssef, H. Ben Ammar","doi":"10.1134/S1070428024100105","DOIUrl":"10.1134/S1070428024100105","url":null,"abstract":"<p> Two new series of 3-(pyrrol-1-yl)thiophene derivatives <b>3a</b>–<b>3c</b> and 3-amino-4-(1,3-benzoxazol-2-yl)-5-(substituted-amino)thiophene derivatives <b>5a</b>–<b>5f</b> were synthesized in 75–85% and up to 91% yields, respectively, from readily available and simple substrates. Substrates <b>2a–2c</b> underwent an amino group change into a pyrrole unit on heating in acetic acid. This protocol has been proven effective by a scaled-up reaction and synthetic transformation. The functional group tolerance and substrate scope of this approach were both approved. It was also possible to prepare substituted thiophenes in a single process. The synthesized thiophene derivatives were tested for their antibacterial effects. The results showed that the presence of a ketone group on the thiophene unit was more efficient compared to the ester group. Compounds <b>2c</b>, <b>5b</b>, and <b>5c</b> showed higher antibacterial activity against both Gram-positive and Gram-negative bacteria. Particularly, compound <b>5b</b> exhibited the highest antibacterial activity with a MIC value of 0.0625 mg/mL against <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i> and with a MIC value of 0.125 mg/mL for <i>Bacillus subtilis</i>, <i>Salmonella enterica</i>, and <i>Pseudomonas aeruginosa</i>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1956 - 1962"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859761","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 Functionally Substituted 4H-Thiopyrans by Reaction of Carbon Disulfide with Malononitrile Trimer","authors":"K. V. Lipin, S. A. Blinov, I. N. Bardasov","doi":"10.1134/S1070428024100038","DOIUrl":"10.1134/S1070428024100038","url":null,"abstract":"<p>Tripotassium 2-(1-cyano-2,2-disulfidoethenyl)-1,1,3,3-tetracyanopropenide was synthesized for the first time by the reaction of carbon disulfide and malononitrile trimer. Its further transformations afforded 2-amino-4-(dicyanomethylidene)-4<i>H</i>-thiopyran-3,5-dicarbonitrile derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1897 - 1900"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024100038.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859758","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis, Identification, and Antibacterial Activity of Thioglycoside Derivatives of 1,3,4-Oxadiazole-2-thiols","authors":"S. J. Abed, M. R. Ahmad","doi":"10.1134/S1070428024100117","DOIUrl":"10.1134/S1070428024100117","url":null,"abstract":"<p>Thioglycoside analogues play an important role in different pharmaceutical products; therefore, we synthesized new thioglycoside analogues containing a 2-sulfanyl-1,3,4-oxadiazole moiety. The main steps of the synthesis were condensation of benzohydrazides with carbon disulfide to form 5-aryl-1,3,4-oxadiazole-2-thiols which were coupled with bromo sugars in the presence of triethylamine to afford the corresponding <i>S</i>-glycoside analogues. The subsequent deprotection of the latter in basic medium gave free thioglycoside derivatives. The structure of all isolated compounds was confirmed by FT-IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. The target products showed good antibacterial activity in vitro.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1963 - 1967"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859762","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. Harutyunyan, S. G. Israelyan, M. S. Safaryan, A. S. Sumbatyan, L. E. Nersesyan, A. S. Aharonyan, I. S. Danielyan, R. E. Muradyan, A. S. Sargsyan, A. A. Hambardzumyan, H. A. Panosyan
{"title":"Synthesis, Molecular Docking Study, and Effect on the Methylation of Tumor DNA of Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidines Functionalized by Aromatic Groups and Azines","authors":"A. A. Harutyunyan, S. G. Israelyan, M. S. Safaryan, A. S. Sumbatyan, L. E. Nersesyan, A. S. Aharonyan, I. S. Danielyan, R. E. Muradyan, A. S. Sargsyan, A. A. Hambardzumyan, H. A. Panosyan","doi":"10.1134/S1070428024100051","DOIUrl":"10.1134/S1070428024100051","url":null,"abstract":"<p>6-Benzyl-4-styrylbenzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-<i>d</i>]pyrimidines and their conjugates with uracil, 5-fluorouracil, and 6-azauracile were synthesized. In addition to the previous findings, it was found that the reaction of 4-methyl-2-phenyl-5,6-dihydrobenzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-<i>d</i>]pyrimidine with aromatic aldehydes in acetic anhydride, depending on the nucleophilicity of the aldehyde carbonyl group, involved both C<sup>6</sup>H<sub>2</sub> methylene group at the α-position with respect to the benzimidazole fragment and the 4-methyl group. The results of molecular docking study of the synthesized compounds and their effect on the methylation of tumor DNA are presented.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1909 - 1920"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859759","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. M. Farzaliyev, M. T. Abbasova, X. K. Efendiyeva, Z. K. Soltanova, L. M. Shahgeldiyeva, L. R. Safarova, N. A. Alieva
{"title":"Synthesis of 3-(Organyloxymethyl)tetrahydro-1,3-oxazines","authors":"V. M. Farzaliyev, M. T. Abbasova, X. K. Efendiyeva, Z. K. Soltanova, L. M. Shahgeldiyeva, L. R. Safarova, N. A. Alieva","doi":"10.1134/S1070428024100087","DOIUrl":"10.1134/S1070428024100087","url":null,"abstract":"<p>3-(Organyloxymethyl)tetrahydro-1,3-oxazines were synthesized by the condensation–heterocyclization of 3-aminopropan-1-ol, formaldehyde, and various hydroxyl-containing compounds. 3,3′-methylenebis(tetrahydro-2<i>H</i>-1,3-oxazine) was also formed as byproduct in ~10% yield. The yield of the title compounds increased in parallel with the length of the hydrocarbon chain in the initial alcohol. Furthermore, the yields of the target products obtained from unbranched alcohols were higher than in the reactions with their branched isomers. The product structure was determined by <sup>13</sup>C NMR spectroscopy. The effect of the organyloxymethyl substituent on the <sup>13</sup>C chemical shifts of the endocyclic carbons in comparison to unsubstituted tetrahydro-1,3-oxazine and 3-methyltetrahydro-1,3-oxazine was studied.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1945 - 1949"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858725","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}
I. I. Stoikov, I. S. Antipin, V. A. Burilov, A. R. Kurbangalieva, N. V. Rostovskii, A. S. Pankova, I. A. Balova, Yu. O. Remizov, L. M. Pevzner, M. L. Petrov, A. V. Vasilyev, A. D. Averin, I. P. Beletskaya, V. G. Nenajdenko, E. K. Beloglazkina, S. P. Gromov, S. S. Karlov, T. V. Magdesieva, A. A. Prishchenko, S. V. Popkov, A. O. Terent’ev, G. V. Tsaplin, T. P. Kustova, L. B. Kochetova, N. A. Magdalinova, E. A. Krasnokutskaya, A. V. Nyuchev, Yu. L. Kuznetsova, A. Yu. Fedorov, A. Yu. Egorova, V. S. Grinev, V. V. Sorokin, K. L. Ovchinnikov, E. R. Kofanov, A. V. Kolobov, V. L. Rusinov, G. V. Zyryanov, E. V. Nosov, V. A. Bakulev, N. P. Belskaya, T. V. Berezkina, D. L. Obydennov, V. Ya. Sosnovskikh, S. G. Bakhtin, O. V. Baranova, V. S. Doroshkevich, G. Z. Raskildina, R. M. Sultanova, S. S. Zlotskii, V. D. Dyachenko, I. V. Dyachenko, A. S. Fisyuk, V. V. Konshin, V. V. Dotsenko, E. A. Ivleva, A. N. Reznikov, Yu. N. Klimochkin, D. A. Aksenov, N. A. Aksenov, A. V. Aksenov, V. V. Burmistrov, G. M. Butov, I. A. Novakov, Kh. S. Shikhaliev, N. V. Stolpovskaya, S. M. Medvedev, N. V. Kandalintseva, O. I. Prosenko, E. B. Menshchikova, A. A. Golovanov, S. Yu. Khashirova
{"title":"Erratum to: Organic Chemistry in Russian Universities. Achievements of Recent Years","authors":"I. I. Stoikov, I. S. Antipin, V. A. Burilov, A. R. Kurbangalieva, N. V. Rostovskii, A. S. Pankova, I. A. Balova, Yu. O. Remizov, L. M. Pevzner, M. L. Petrov, A. V. Vasilyev, A. D. Averin, I. P. Beletskaya, V. G. Nenajdenko, E. K. Beloglazkina, S. P. Gromov, S. S. Karlov, T. V. Magdesieva, A. A. Prishchenko, S. V. Popkov, A. O. Terent’ev, G. V. Tsaplin, T. P. Kustova, L. B. Kochetova, N. A. Magdalinova, E. A. Krasnokutskaya, A. V. Nyuchev, Yu. L. Kuznetsova, A. Yu. Fedorov, A. Yu. Egorova, V. S. Grinev, V. V. Sorokin, K. L. Ovchinnikov, E. R. Kofanov, A. V. Kolobov, V. L. Rusinov, G. V. Zyryanov, E. V. Nosov, V. A. Bakulev, N. P. Belskaya, T. V. Berezkina, D. L. Obydennov, V. Ya. Sosnovskikh, S. G. Bakhtin, O. V. Baranova, V. S. Doroshkevich, G. Z. Raskildina, R. M. Sultanova, S. S. Zlotskii, V. D. Dyachenko, I. V. Dyachenko, A. S. Fisyuk, V. V. Konshin, V. V. Dotsenko, E. A. Ivleva, A. N. Reznikov, Yu. N. Klimochkin, D. A. Aksenov, N. A. Aksenov, A. V. Aksenov, V. V. Burmistrov, G. M. Butov, I. A. Novakov, Kh. S. Shikhaliev, N. V. Stolpovskaya, S. M. Medvedev, N. V. Kandalintseva, O. I. Prosenko, E. B. Menshchikova, A. A. Golovanov, S. Yu. Khashirova","doi":"10.1134/S1070428024100257","DOIUrl":"10.1134/S1070428024100257","url":null,"abstract":"","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2052 - 2053"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859592","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":"Novel Bis-spiro-β-lactams Derived from Some Quinolinones via the Staudinger Synthesis","authors":"E. J. Fadhil, A. O. Hammady, A. N. Ayyash","doi":"10.1134/S1070428024100130","DOIUrl":"10.1134/S1070428024100130","url":null,"abstract":"<p>A series of novel bis-spiro-β-lactams were obtained by the Staudinger synthesis. Pyrazine-2,3-dicarboxylic acid was cyclized with thiosemicarbazide to yield bis-2-amino-1,3,4-thiadiazole derivative which was further condensed with some commercial quinolinone derivatives to give imines. The reaction of these new imines with phenoxyacetyl chloride in the presence of triethylamine afforded spiro-β-lactams. The structures of the synthesized compounds were deduced from their FTIR, <sup>1</sup>H NMR, and <sup>13</sup>C NMR spectra, and elemental analyses.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1980 - 1983"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859691","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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