3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Methods
3.2. General Procedure for the Cycloaddition of Alkenes and α-Nitroketones
3.2.1. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (3a)
3.2.2. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(2-bromophenyl)methanone (3b)
3.2.3. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(3-bromophenyl)methanone (3c)
3.2.4. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(4-bromophenyl)methanone (3d)
3.2.5. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(p-tolyl)methanone (3e)
3.2.6. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(4-methoxyphenyl)methanone (3f)
3.2.7. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(4-tert-butylphenyl)methanone (3g)
3.2.8. [1,1′-Biphenyl]-4-yl(5-benzyl-4,5-dihydroisoxazol-3-yl)methanone (3h)
3.2.9. Methyl 5-benzyl-4,5-dihydroisoxazole-3-carboxylate (3i)
3.2.10. (5-(2-Methylbenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5a)
3.2.11. (5-(3-Methylbenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5b)
3.2.12. (5-(4-Methylbenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5c)
3.2.13. (5-(4-Methoxybenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5d)
3.2.14. (5-Octyl-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5e)
3.2.15. (5-(Chloromethyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5f)
3.2.16. (3a,4,5,6,7,7a-Hexahydrobenzo[d]isoxazol-3-yl)(phenyl)methanone (5g)
3.2.17. Ethyl 3-benzoyl-4,5-dihydroisoxazole-5-carboxylate (7a)
3.2.18. (5-Butylisoxazol-3-yl)(phenyl)methanone (7b)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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| |||
---|---|---|---|
Entry | Catalyst | Amount of Base (mol) | Yield b (%) of 3a |
1 | -- | -- | <5 |
2 | Imidazole | 0.5 | 43 |
3 | 4-Dimethylaminopyridine | 0.5 | 45 |
4 | Triethylamine | 0.5 | 55 |
5 | N,N,N’,N’-Tetramethylethylenediamine | 0.5 | 48 |
6 | Chloramine-T | 0.5 | 77 |
7 | Chloramine-T | 1.0 | 52 |
8 | Chloramine-T | 0.25 | 68 |
9 | Chloramine-T | 0.1 | 65 |
10 c | Chloramine-T | 0.5 | 46 |
11 d | Chloramine-T | 0.5 | 40 |
12 e | Chloramine-T | 0.5 | 11 |
13 f | Chloramine-T | 0.5 | 36 |
14 g | Chloramine-T | 0.5 | 70 |
15 h | Chloramine-T | 0.5 | 59 |
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Pan, X.; Xin, X.; Mao, Y.; Li, X.; Zhao, Y.; Liu, Y.; Zhang, K.; Yang, X.; Wang, J. 3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles. Molecules 2021, 26, 3491. https://doi.org/10.3390/molecules26123491
Pan X, Xin X, Mao Y, Li X, Zhao Y, Liu Y, Zhang K, Yang X, Wang J. 3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles. Molecules. 2021; 26(12):3491. https://doi.org/10.3390/molecules26123491
Chicago/Turabian StylePan, Xinhui, Xiaobing Xin, Ying Mao, Xin Li, Yanan Zhao, Yidi Liu, Ke Zhang, Xiaoda Yang, and Jinhui Wang. 2021. "3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles" Molecules 26, no. 12: 3491. https://doi.org/10.3390/molecules26123491