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通过亚甲胺叶立德与烯烃的多种环化反应合成功能化吡咯衍生物。

Synthesis of functionalized pyrrole derivatives via diverse cyclization of azomethine ylide and olefins.

机构信息

Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Vakilabad Blvd., Mashhad, 91775-1436, Iran.

出版信息

Mol Divers. 2022 Aug;26(4):2221-2230. doi: 10.1007/s11030-021-10328-x. Epub 2021 Oct 15.

Abstract

The azomethine ylides are generally used in 1,3-dipolar cycloadditions with various dipolarophiles. In this work, a new and diverse route has been developed for the azomethine ylides, for synthesis of novel pyrrole derivatives. The azomethine ylide, produced via C-H activation of unreactive C(sp)-H bond of 2-methylquinoline, by molecular iodine, in the presence of pyridine. Herein, we represent novel pyrrole derivatives, synthesized from the reaction of pyridinium ylide with olefins, which formed via a reaction of isatin, dialkyl acetylenedicarboxylate derivatives and pyridine as a base in moderate to excellent yields. Various features of this cyclization, discussed.

摘要

亚甲胺叶立德通常用于与各种偶极子的 1,3-偶极环加成反应。在这项工作中,为合成新型吡咯衍生物,开发了一种新的、多样化的亚甲胺叶立德合成方法。亚甲胺叶立德通过分子碘在吡啶存在下对 2-甲基喹啉的惰性 C(sp)-H 键的 C-H 活化产生。在此,我们代表了新型吡咯衍生物,它们是通过色胺、二烷基丙二酸盐衍生物和吡啶作为碱反应生成的吡啶翁叶立德与烯烃反应合成的,产率中等至优秀。讨论了这种环化反应的各种特点。

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