V. R. Akhmetova, D. V. Leont’ev, V. R. Nigmatullina, E. A. Paramonov, N. F. Galimzyanova, A. S. Ryabova
{"title":"吲哚与甲醛、二硫化碳和胺的多组分反应","authors":"V. R. Akhmetova, D. V. Leont’ev, V. R. Nigmatullina, E. A. Paramonov, N. F. Galimzyanova, A. S. Ryabova","doi":"10.1134/S1070363225604260","DOIUrl":null,"url":null,"abstract":"<p>The multicomponent reaction (MCR) of indole with formaldehyde, carbon disulfide, and amines catalyzed with various catalysts was studied as a method for the synthesis of 3-dithiocarbamatomethylindoles. It was shown that zwitterionic catalysts (taurine, <i>N</i>-methylpyridinium iodide) direct the reaction towards dithiocarbamate methylation of indole, whereas basic catalysts (NaOH, Py, TEA) are non-selective and primarily initiate the indole aminomethylation. The synthesized 3-dithiocarbamatomethylindoles were evaluated for antimicrobial activity. It was found that among the synthesized compounds, 1<i>H</i>-indol-3-ylmethyl dimethylcarbamodithioate exhibits the highest antimicrobial activity against phytopathogenic fungi (<i>Bipolaris sorokiniana</i>, <i>Botrytis cinerea</i>, <i>Fusarium oxysporum</i>, <i>Rhizoctonia solani</i>) and bacteria non-pathogenic to humans (gram-positive <i>Bacillus subtilis</i> IB-54 and gram-negative <i>Pseudomonas mandelii</i> IB-K14).</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"95 9","pages":"2691 - 2698"},"PeriodicalIF":0.8000,"publicationDate":"2025-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Multicomponent Reaction of Indole with Formaldehyde, Carbon Disulfide, and Amines\",\"authors\":\"V. R. Akhmetova, D. V. Leont’ev, V. R. Nigmatullina, E. A. Paramonov, N. F. Galimzyanova, A. S. Ryabova\",\"doi\":\"10.1134/S1070363225604260\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The multicomponent reaction (MCR) of indole with formaldehyde, carbon disulfide, and amines catalyzed with various catalysts was studied as a method for the synthesis of 3-dithiocarbamatomethylindoles. It was shown that zwitterionic catalysts (taurine, <i>N</i>-methylpyridinium iodide) direct the reaction towards dithiocarbamate methylation of indole, whereas basic catalysts (NaOH, Py, TEA) are non-selective and primarily initiate the indole aminomethylation. The synthesized 3-dithiocarbamatomethylindoles were evaluated for antimicrobial activity. It was found that among the synthesized compounds, 1<i>H</i>-indol-3-ylmethyl dimethylcarbamodithioate exhibits the highest antimicrobial activity against phytopathogenic fungi (<i>Bipolaris sorokiniana</i>, <i>Botrytis cinerea</i>, <i>Fusarium oxysporum</i>, <i>Rhizoctonia solani</i>) and bacteria non-pathogenic to humans (gram-positive <i>Bacillus subtilis</i> IB-54 and gram-negative <i>Pseudomonas mandelii</i> IB-K14).</p>\",\"PeriodicalId\":761,\"journal\":{\"name\":\"Russian Journal of General Chemistry\",\"volume\":\"95 9\",\"pages\":\"2691 - 2698\"},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2025-10-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Journal of General Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S1070363225604260\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of General Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070363225604260","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Multicomponent Reaction of Indole with Formaldehyde, Carbon Disulfide, and Amines
The multicomponent reaction (MCR) of indole with formaldehyde, carbon disulfide, and amines catalyzed with various catalysts was studied as a method for the synthesis of 3-dithiocarbamatomethylindoles. It was shown that zwitterionic catalysts (taurine, N-methylpyridinium iodide) direct the reaction towards dithiocarbamate methylation of indole, whereas basic catalysts (NaOH, Py, TEA) are non-selective and primarily initiate the indole aminomethylation. The synthesized 3-dithiocarbamatomethylindoles were evaluated for antimicrobial activity. It was found that among the synthesized compounds, 1H-indol-3-ylmethyl dimethylcarbamodithioate exhibits the highest antimicrobial activity against phytopathogenic fungi (Bipolaris sorokiniana, Botrytis cinerea, Fusarium oxysporum, Rhizoctonia solani) and bacteria non-pathogenic to humans (gram-positive Bacillus subtilis IB-54 and gram-negative Pseudomonas mandelii IB-K14).
期刊介绍:
Russian Journal of General Chemistry is a journal that covers many problems that are of general interest to the whole community of chemists. The journal is the successor to Russia’s first chemical journal, Zhurnal Russkogo Khimicheskogo Obshchestva (Journal of the Russian Chemical Society ) founded in 1869 to cover all aspects of chemistry. Now the journal is focused on the interdisciplinary areas of chemistry (organometallics, organometalloids, organoinorganic complexes, mechanochemistry, nanochemistry, etc.), new achievements and long-term results in the field. The journal publishes reviews, current scientific papers, letters to the editor, and discussion papers.