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三氟甲磺酸银(I)催化的吡唑并二氮杂䓬的Ugi反应后合成。

Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines.

作者信息

Hasan Muhammad, Peshkov Anatoly A, Shah Syed Anis Ali, Belyaev Andrey, Lim Chang-Keun, Wang Shunyi, Peshkov Vsevolod A

机构信息

College of Chemistry Chemical Engineering and Material Science, Soochow University, Suzhou, 215123, P.R. China.

Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, Astana, 010000, Kazakhstan.

出版信息

Beilstein J Org Chem. 2025 May 8;21:915-925. doi: 10.3762/bjoc.21.74. eCollection 2025.

Abstract

A silver(I) triflate-catalyzed post-Ugi assembly of novel pyrazolo[1,5-][1,4]diazepine scaffolds is reported offering high yields (up to 98%) under mild conditions. The synthetic sequence involves the Ugi four-component reaction (U4CR) of pyrazole-3-carbaldehydes, primary amines, 3-substituted propiolic acids, and isocyanides, followed by a silver(I) triflate-catalyzed intramolecular heteroannulation of the resulting pyrazole-tethered propargylamides occurring in a 7-- fashion. The approach is scalable and tolerates a diverse range of substitution patterns.

摘要

据报道,一种三氟甲磺酸银(I)催化的新型吡唑并[1,5 - ][1,4]二氮杂卓支架的Ugi后组装反应,在温和条件下可提供高产率(高达98%)。合成序列包括吡唑 - 3 - 甲醛、伯胺、3 - 取代的炔丙酸和异腈的Ugi四组分反应(U4CR),随后是三氟甲磺酸银(I)催化的所得吡唑连接的炔丙酰胺的分子内杂环化反应,该反应以7 - 方式进行。该方法具有可扩展性,并且能够耐受多种取代模式。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bce9/12067096/042bcdaf50fa/Beilstein_J_Org_Chem-21-915-g002.jpg

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