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鏻酸性离子液体:一种用于合成2-芳基苯并恶唑、2-芳基苯并咪唑和2-芳基苯并噻唑的高效且可循环使用的均相催化剂。

Phosphonium acidic ionic liquid: an efficient and recyclable homogeneous catalyst for the synthesis of 2-arylbenzoxazoles, 2-arylbenzimidazoles, and 2-arylbenzothiazoles.

作者信息

Nguyen Quang The, Thi Hang Anh-Hung, Ho Nguyen Thuy-Linh, Nguyen Chau Duy-Khiem, Tran Phuong Hoang

机构信息

Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University - Ho Chi Minh City 721337 Viet Nam

Center for Innovative Materials and Architectures, Vietnam National University - Ho Chi Minh City 721337 Viet Nam.

出版信息

RSC Adv. 2018 Mar 27;8(21):11834-11842. doi: 10.1039/c8ra01709c. eCollection 2018 Mar 21.

Abstract

A highly efficient and green strategy for the synthesis of 2-arylbenzoxazoles, 2-arylbenzimidazoles, and 2-arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed the condensation of -aminophenol, -phenylenediamines, and -aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by H NMR, C NMR, P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

摘要

已开发出一种由鏻酸性离子液体催化合成2-芳基苯并恶唑、2-芳基苯并咪唑和2-芳基苯并噻唑的高效绿色策略,分别是邻氨基酚、邻苯二胺和邻氨基苯硫酚与醛的缩合反应。该反应产率高、底物范围广且条件温和。三苯基(丁基-3-磺酰基)鏻甲苯磺酸盐催化剂可通过一锅法从廉价易得的起始原料轻松制得。通过¹H NMR、¹³C NMR、³¹P NMR和FT-IR技术对其结构进行了鉴定。通过TGA和哈米特酸度函数法测定了包括热稳定性和酸度在内的其他性质。有趣的是,该催化剂在第四次回收时仍能保持其持续优异的性能。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d58/9079114/6e82bdd3d890/c8ra01709c-f1.jpg

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