Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones,Organic Letters

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Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones
Organic Letters ( IF 4.9 ) Pub Date : 2020-09-28 , DOI: 10.1021/acs.orglett.0c02821
Bianca T. Matsuo ₁ , José Tiago M. Correia ₁ , Márcio W. Paixão ₁

Affiliation

Herein, a mild and robust photocatalytic protocol for the combination of amino and pyrazolidinone functionalities through a radical α-amino alkylation of azomethine iminium ions is demonstrated. This method presents a high functional group tolerance providing direct access to a large family of N-(β-aminoalkyl)pyrazolidinones in good to excellent yields, including the late-stage incorporation of the pyrazolidinone moiety to pharmaceutical ingredients. We propose a plausible scenario for the C–C bond-forming step which involves radical addition followed by a spin-center-shift event.

中文翻译：

可见光介导的甲亚胺亚胺的α-氨基烷基化：N-（β-氨基烷基）吡唑烷酮的一种方法

在本文中，展示了一种温和且坚固的光催化方案，用于通过偶氮甲碱亚胺离子的自由基α-氨基烷基化来结合氨基和吡唑烷酮官能团。该方法具有很高的官能团耐受性，可以以良好至极佳的收率直接进入大家族的N-（β-氨基烷基）吡唑烷酮，包括将吡唑烷酮部分后期掺入药物成分中。我们为C–C键形成步骤提出了一种可行的方案，该方案涉及自由基加成，然后发生自旋中心移位事件。

更新日期：2020-10-17

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