3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles

Xinhui Pan; Xiaobing Xin; Ying Mao; Xin Li; Yanan Zhao; Yidi Liu; Ke Zhang; Xiaoda Yang; Jinhui Wang

doi:10.3390/molecules26123491

3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles

Molecules. 2021 Jun 8;26(12):3491. doi: 10.3390/molecules26123491.

Authors

Xinhui Pan^{1

2}, Xiaobing Xin^{2

3}, Ying Mao⁴, Xin Li², Yanan Zhao², Yidi Liu², Ke Zhang², Xiaoda Yang^{1

2}, Jinhui Wang²

Affiliations

¹ Stake Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
² Key Laboratory of Xinjiang Phytomedicine Resource and Utilisation, Ministry of Education, School of Pharmaceutical Sciences, Shihezi University, Shihezi 832002, China.
³ Department of Pharmacology, Houbo College of Xinjiang Medical University, Karamay 834000, China.
⁴ School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China.

Abstract

In this study, 3-benzoylisoxazolines were synthesized by reacting alkenes with various α-nitroketones using chloramine-T as the base. The scope of α-nitroketones and alkenes is extensive, including different alkenes and alkynes to form various isoxazolines and isoxazoles. The use of chloramine-T, as the low-cost, easily handled, moderate base for 1,3-dipolar cycloaddition is attractive.

Keywords: 1,3-dipolar cycloaddition; alkenes; chloramine-T; isoxazolines; α-nitroketones.

Abstract

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