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由酮和乙腈电化学合成多取代恶唑

Electrochemical Synthesis of Polysubstituted Oxazoles from Ketones and Acetonitrile.

作者信息

Bao Liang, Liu Chen, Li Wenyi, Yu Jiage, Wang Min, Zhang Yunfei

机构信息

Department of Chemistry, China Agricultural University, Beijing100193, P. R. China.

出版信息

Org Lett. 2022 Aug 12;24(31):5762-5766. doi: 10.1021/acs.orglett.2c02252. Epub 2022 Jul 31.

Abstract

Herein we report an electrochemical strategy for the construction of polysubstituted oxazoles from easily available ketones and acetonitrile under room temperature. The method shows high efficiency, a broad substrate scope, and requires no external chemical oxidant. Mechanistic investigations suggest that the reaction proceeds through a Ritter-type reaction/oxidative cyclization using acetonitrile as the reactant and solvent. X-ray crystallographic analysis reveals that the reaction involves the attack of acetonitrile on the carbonyl carbon instead of the α-carbon.

摘要

在此,我们报道了一种在室温下由易得的酮和乙腈构建多取代恶唑的电化学策略。该方法显示出高效率、广泛的底物范围,并且不需要外部化学氧化剂。机理研究表明,该反应通过使用乙腈作为反应物和溶剂的 Ritter 型反应/氧化环化进行。X 射线晶体学分析表明,该反应涉及乙腈对羰基碳而非α-碳的进攻。

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