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用于合成高官能化螺内酰胺的电化学后乌吉环化反应

Electrochemical Post-Ugi Cyclization for the Synthesis of Highly Functionalized Spirolactams.

作者信息

Nagar Riya, Suwalka Dinesh, Malviya Bhanwar Kumar, Verma Ved Prakash, Jassal Amanpreet Kaur, Sharma Siddharth

机构信息

Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India.

Department of Chemistry, Banasthali University, Niwai-Jodhpuriya Road, Vanasthali 304022, India.

出版信息

J Org Chem. 2023 Oct 6;88(19):13977-13994. doi: 10.1021/acs.joc.3c01532. Epub 2023 Sep 11.

Abstract

The combination of the Ugi reaction and electro-organic synthesis can aid in the creation of novel heterocycles that have not been previously explored. In this study, a new strategy utilizing bis-amides from the Ugi reaction has been developed, which can produce C-S, C-Se, and C-C═O functionalized five-membered spirolactams mediated by electricity under catalyst- and metal-free conditions. Notably, this approach can be applied using a microelectro-flow reactor (μ-EFR) for gram-scale synthesis. The described strategy can synthesize complex azaspiro-fused tricyclic scaffolds with high diastereo- and regioselectivity, highlighting its versatility and potential.

摘要

乌吉反应与有机电合成相结合有助于创造出以前未被探索过的新型杂环化合物。在本研究中,开发了一种利用乌吉反应中的双酰胺的新策略,该策略可以在无催化剂和无金属条件下通过电介导生成碳-硫、碳-硒和碳-碳═O官能化的五元螺内酰胺。值得注意的是,这种方法可以使用微电流动反应器(μ-EFR)进行克级规模的合成。所描述的策略可以以高非对映选择性和区域选择性合成复杂的氮杂螺稠合三环支架,突出了其多功能性和潜力。

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