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

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

Xinhui Pan  1   2 , Xiaobing Xin  2   3 , Ying Mao  4 , Xin Li  2 , Yanan Zhao  2 , Yidi Liu  2 , Ke Zhang  2 , Xiaoda Yang  1   2 , Jinhui Wang  2
Affiliations

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

Xinhui Pan et al. Molecules. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Examples of important isoxazolines.
Figure 2
Figure 2
Application of 2-isoxazoline as a key building block.
Scheme 1
Scheme 1
Scope of cycloaddition.
Scheme 2
Scheme 2
Scope of alkenes.
Scheme 3
Scheme 3
The reaction of 1a with 6 in the presence of chloramine-T in CH3CN.
Scheme 4
Scheme 4
A plausible mechanism for the condensation of nitro compounds and dipolarophiles.
See this image and copyright information in PMC

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