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光氧化还原/铜共催化肟酯与NHSCN的多米诺环化反应:全取代2-氨基噻唑的合成方法

Photoredox/Copper-Cocatalyzed Domino Annulation of Oxime Esters and NHSCN: Access to Fully Substituted 2-Aminothiazoles.

作者信息

Luo Yongyan, Zhang Yanyan, Liu Mengting, Wang Xiaozhen, Wan Yichao, Cao Shujun

机构信息

Key Laboratory of Theoretical Organic Chemistry and Functional Molecule, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.

出版信息

J Org Chem. 2024 Oct 18;89(20):15187-15196. doi: 10.1021/acs.joc.4c01951. Epub 2024 Oct 7.

Abstract

Domino cyclization of oxime esters and NHSCN facilitated by photoredox and copper cocatalysis has been established. Various structurally diverse fully substituted 2-aminothiazoles have been obtained in good yields at room temperature. It is featured by mild conditions, favorable functional group tolerance, and wide substrate scope. The present reaction is amenable to gram-scale synthesis, which is expected to find potential applications in organic synthesis and drug discovery. A plausible reaction mechanism is proposed.

摘要

通过光氧化还原和铜共催化实现的肟酯和NHSCN的多米诺环化反应已被确立。在室温下以良好的产率获得了各种结构多样的全取代2-氨基噻唑。该反应具有条件温和、官能团耐受性良好和底物范围广泛的特点。目前的反应适用于克级规模的合成,有望在有机合成和药物发现中找到潜在应用。提出了一种合理的反应机理。

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