An Oxidative [3+2+1] Cyclization of Enaminones and N-Alkenyl-2-pyrrolidinone: Access to Polysubstituted 4-Alkylated 1,4-dihydropyridines,Advanced Synthesis & Catalysis

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An Oxidative [3+2+1] Cyclization of Enaminones and N-Alkenyl-2-pyrrolidinone: Access to Polysubstituted 4-Alkylated 1,4-dihydropyridines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-03-25 , DOI: 10.1002/adsc.202300088
Zhangmengjie Chai ₁ , Longkun Chen ₁ , Zhuoyuan Liu ₁ , Yulin Sun ₁ , Donghan Liu ₁ , Mingshuai Zhang ₁ , Yongchao Wang ₂ , Fuchao Yu ₁

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An oxidative [3+2+1] cyclization of enaminones and N-alkenyl-2-pyrrolidinone is described for the synthesis of 4-alkylated 1,4-dihydropyridines (1,4-DHPs). By using terminal olefin as the C4 source of the 1,4-DHP skeleton, this synthetic strategy provides a series of 1,4-DHPs through a 1,1-difunctionalization/cyclization process. In this protocol, two C(sp³)−C(sp²) bonds and a C(sp²)−N bond are simultaneously formed, the hydrogen source on the newly formed methyl group of the 1,4-DHP skeleton is confirmed and a possible mechanism is proposed.

中文翻译：

烯胺酮和 N-烯基-2-吡咯烷酮的氧化 [3+2+1] 环化：获得多取代的 4-烷基化 1,4-二氢吡啶

烯胺酮和N -烯基-2-吡咯烷酮的氧化 [3+2+1] 环化用于合成 4-烷基化 1,4-二氢吡啶 (1,4-DHP)。通过使用末端烯烃作为 1,4-DHP 骨架的 C4 来源，该合成策略通过 1,1-双官能化/环化过程提供了一系列 1,4-DHP。在该方案中，两个C( sp ³ )−C( sp ² )键和一个C( sp ² )−N键同时形成，确认了1,4-DHP骨架新形成的甲基上的氢源并提出了一种可能的机制。

更新日期：2023-03-25

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