Reactions of phosphonium-iodonium ylides with alkynes as a process of targeted synthesis of phosphorus-containing heterocycles: photoinduction and assistance of dipolarophiles

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2025-03-25 DOI:10.1007/s11172-025-4511-z
I. D. Potapov, A. S. Nenashev, I. I. Levina, Yu. V. Timchenko, I. A. Rodin, I. A. Shutkov, A. A. Nazarov, G. M. Kuramshina, M. V. Motyakin, T. D. Nekipelova, T. A. Podrugina
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Abstract

The heterocyclization reaction of mixed phosphonium-iodonium ylides with alkynes in the presence of various dipolarophiles was studied in order to identify the dependence of the process result on the dipolarophile nature. The library of phosphinolines and phosphonium-substituted furans obtained under the conditions of this process was expanded. The studies, including quantum chemical calculations, were conducted to reveal the influence of the nature of substituents in the iodonium fragment on the reactivity of mixed ylides in heterocyclization reactions. The antiproliferative activity of new compounds was studied and phosphonium-substituted furans were found in some cases to demonstrate higher activity in human cancer cell lines compared to cisplatin.

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磷-碘吡啶与炔的反应定向合成含磷杂环:光诱导和亲偶极试剂的辅助
研究了在多种亲偶极试剂存在下,混合磷-碘吡啶与炔的杂环化反应,以确定反应结果与亲偶极试剂性质的关系。扩大了在此条件下得到的膦碱和磷取代呋喃的文库。研究包括量子化学计算,揭示了碘碎片中取代基的性质对杂环化反应中混合杂环化反应活性的影响。研究了新化合物的抗增殖活性,发现在某些情况下,与顺铂相比,磷取代呋喃在人类癌细胞系中表现出更高的活性。
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来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
期刊介绍: Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.
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