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铁(0)催化的硝基芳烃与醇的转移氢缩合反应:苯并恶唑、苯并噻唑和苯并咪唑的简便合成方法。

Iron(0)-Catalyzed Transfer Hydrogenative Condensation of Nitroarenes with Alcohols: A Straightforward Approach to Benzoxazoles, Benzothiazoles, and Benzimidazoles.

机构信息

BK 21 Plus Project, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

出版信息

J Org Chem. 2020 Dec 4;85(23):15396-15405. doi: 10.1021/acs.joc.0c02191. Epub 2020 Nov 2.

Abstract

The iron-catalyzed hydrogen transfer strategy has been applied to the redox condensation of -hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism. Furthermore, the reaction system was successfully extended to the synthesis of benzothiazoles and benzimidazoles.

摘要

铁催化的氢转移策略已被应用于 -羟基硝基苯与醇的氧化还原缩合反应,生成苯并恶唑衍生物。在没有外加氧化还原试剂的情况下,以良好至优异的收率合成了一系列 2-取代的苯并恶唑。一系列对照实验提供了一个合理的反应机制。此外,该反应体系还成功扩展到苯并噻唑和苯并咪唑的合成中。

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