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以赤藓红B为光催化剂的可见光介导的吡唑并[1,5 - ]嘧啶的区域选择性C3 - H硒化反应

Visible-Light-Mediated Regioselective C3-H Selenylation of Pyrazolo[1,5-]pyrimidines Using Erythrosine B as Photocatalyst.

作者信息

Choudhuri Tathagata, Paul Suvam, Das Sourav, Pathak Devendra Deo, Bagdi Avik Kumar

机构信息

Department of Chemistry, University of Kalyani, Kalyani 741235, India.

Department of Chemistry & Chemical Biology, Indian Institute of Technology (ISM), Dhanbad 826 004, India.

出版信息

J Org Chem. 2023 Jul 7;88(13):8992-9003. doi: 10.1021/acs.joc.3c00720. Epub 2023 Jun 11.

DOI:10.1021/acs.joc.3c00720
PMID:37302135
Abstract

A visible-light-induced efficient methodology has been developed for the C-H selenylation of pyrazolo[1,5-]pyrimidine derivatives employing erythrosine B as the photocatalyst. This is the first report on the regioselective selenylation of pyrazolo[1,5-]pyrimidines. The efficiency of this methodology for the selenylation of different electron-rich heterocycles like pyrazole, indole, imidazo[1,2-]pyridine, imidazo[2,1-]thiazole, and 4-(phenylamino)-2-chromen-2-one has been also demonstrated. The exploration of erythrosine B as a photocatalyst with a simple and mild procedure, wide substrate scope, and practical applicability and the employment of eco-friendly energy, oxidant, and solvent are the attractive characteristics of this methodology.

摘要

已经开发出一种可见光诱导的高效方法,以赤藓红B作为光催化剂,用于吡唑并[1,5 - ]嘧啶衍生物的C-H硒化反应。这是关于吡唑并[1,5 - ]嘧啶区域选择性硒化的首次报道。该方法对不同富电子杂环(如吡唑、吲哚、咪唑并[1,2 - ]吡啶、咪唑并[2,1 - ]噻唑和4 -(苯氨基)-2 - 色烯 - 2 - 酮)进行硒化反应的效率也得到了证明。赤藓红B作为光催化剂具有操作简单温和、底物范围广、实际适用性强等特点,并且使用了环保型能源、氧化剂和溶剂,这些都是该方法吸引人的特性。

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