Multicomponent Reaction of Indole with Formaldehyde, Carbon Disulfide, and Amines

IF 0.8 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Russian Journal of General Chemistry Pub Date : 2025-10-07 DOI:10.1134/S1070363225604260

V. R. Akhmetova, D. V. Leont’ev, V. R. Nigmatullina, E. A. Paramonov, N. F. Galimzyanova, A. S. Ryabova

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Abstract

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).

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吲哚与甲醛、二硫化碳和胺的多组分反应

研究了吲哚与甲醛、二硫化碳和胺在不同催化剂催化下的多组分反应（MCR），合成3-二硫代氨基乙基吲哚。结果表明，两性离子催化剂（牛磺酸、n-甲基碘化吡啶）直接催化吲哚的二硫代氨基甲酸酯甲基化反应，而碱性催化剂（NaOH、Py、TEA）则是非选择性的，主要引发吲哚的氨基甲基化反应。对合成的3-二硫代氨基乙基吲哚进行了抗菌活性评价。结果表明，合成的化合物中，h -吲哚-3-基甲基二甲氨基二硫代酸酯对植物病原真菌（双极真菌、灰霉病菌、尖孢镰刀菌、solani根丝胞菌）和非致病性细菌（革兰氏阳性枯草芽孢杆菌IB-54和革兰氏阴性曼氏假单胞菌IB-K14）的抑菌活性最高。

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来源期刊

Russian Journal of General Chemistry 化学-化学综合

CiteScore

1.40

自引率

22.20%

发文量

252

审稿时长

2-4 weeks

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.