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DOI: 10.1055/a-2735-9351
Three-Component Reaction of N-(Sulfonyl)acrylamides, Tert-Butyl nitrite, and Acetone: Preparation of Isoxazole Compounds
Autoren
We gratefully thank the Key R&D Program of Shandong Province (Major Science and Technology Innovation Project) (Project No. 2024CXGC010609) for financial support.

Abstract
Herein, we present a simple, efficient, and additive-free multicomponent, tandem method for synthesizing a series of isoxazole frameworks. By using readily available N-(sulfonyl)-acrylamide with tert-butyl nitrite in acetone at 110 °C for 12 h, we successfully synthesized the target compounds. This method demonstrates excellent substrate compatibility, yielding a total of 22 target compounds, with the highest yield reaching 83%. In conclusion, the proposed method offers a reliable and straightforward approach to the synthesis of structurally diverse isoxazole frameworks.
Keywords
N-(sulfonyl)-acrylamide - Tandem reaction - C–H activation - Isoxazole frameworks - 1,3-Dipolar cycloadditionPublikationsverlauf
Eingereicht: 23. Juli 2025
Angenommen nach Revision: 17. Oktober 2025
Artikel online veröffentlicht:
26. November 2025
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References
- 1a Berthet M, Cheviet T, Dujardin J. Chem Rev 2016; 116: 15235-15283
- 1b Kumar G, Shankar R. ChemMedChem 2021; 16: 430-447
- 1c D’Ascenzio M, Secci D, Carradori S. et al. J Med Chem 2020; 63: 2470-2488
- 1d Puttaswamy N, Pavan Kumar GS, Al-Ghorbani M, Vigneshwaran V, Prabhakar BT, Khanum SA. Eur J Med Chem 2016; 114: 153-161
- 1e Lingaraju GS, Balaji KS, Jayarama S, Anil SM, Kiran KR, Sadashiva MP. Bioorg Med Chem Lett 2018; 28: 3606-3612
- 2a Charest MG, Lerner CD, Brubaker JD, Siegel DR, Myers AG. Science 2005; 308: 395-398
- 2b Minter AR, Fuller AA, Mapp AK. J Am Chem Soc 2003; 125: 6846-6847
- 2c Fuller AA, Chen B, Minter AR, Mapp AK. J Am Chem Soc 2005; 127: 5376-5383
- 2d Jiang D, Peng J, Chen Y. Org Lett 2008; 10: 1695-1698
- 3a Sedenkova KN, Andriasov S, Eremenko MG. et al. Molecules 2022; 27: 3546
- 3b Kamal A, Bharathi EV, Reddy JS. et al. Eur J Med Chem 2011; 46: 691-703
- 4a Brabham C, Johnen P, Hendriks J. et al. Weed Sci 2021; 69: 18-30
- 4b Koo SJ, Hwang KH, Jeon MS. et al. Pest Manage Sci 2014; 70: 156-162
- 5a Adiloğlu Y, Şahin E, Tutar A, Menzek AJ. Heterocycl Chem 2018; 55: 1917-1925
- 5b Song XM, Wang HJ, Zou W. et al. J Agric Food Chem 2025; 73: 6589-6598
- 5c Liu ZY, Han MY, Yan XT. et al. J Agric Food Chem 2022; 70: 7921-7928
- 5d Huang SS, Ma HN, Wang ZW. et al. J Agric Food Chem 2023; 71: 5107-5116
- 6a Huang HW, Li FF, Xu ZH, Cai JH, Ji XC, Deng GJ. Adv Synth Catal 2017; 359: 3102-3107
- 6b Mallick S, Baidya M, Mahanty K, Maiti D, De Sarkar S. Adv Synth Catal 2020; 362: 1046-1052
- 6c Antonova YA, Nelyubina YV, Ioffe SL, Sukhorukov AY, Tabolin AA. Adv Synth Catal 2022; 364: 2606-2612
- 6d Vara V, Thete KR, Ghotekar GS, Muthukrishnan M. Chem Asian J 2025; 20: e202401079
- 6e Liu SR, Ying ZM, Zhu Q. et al. Org Chem Front 2023; 10: 3269-3274
- 6f Gao WC, Li BB, Zong LY. et al. Eur J Org Chem 2021; 2431-2435
- 6g Jimoh AA, Hosseyni S, Ye XH, Wojtas L, Hu Y, Shi XD. Chem Commun 2019; 55: 8150-8153
- 7 Gao MC, Li YY, Gan YS, Xu B. Angew Chem Int Ed 2015; 54: 8795-8799
- 8 Chen F, Zhu FF, Zhang M, Liu RH, Yu W, Han B. Org Lett 2017; 19: 3255-3258
- 9 Ma L, Jin F, Cheng XL. et al. Chem Sci 2021; 12: 9823-9830
- 10a Liang YF, Li XY, Wang XY, Yan YP, Feng P, Jiao N. ACS Catal 2015; 5: 1956-1963
- 10b Sau P, Santra SK, Rakshit A, Patel BK. J Org Chem 2017; 82: 6358-6365
- 10c Zhu YH, Mao J, Ma QY, Zhang SW, Yuan Y, Jia XD. J Org Chem 2025; 90: 2459-2471
- 10d Prasad SS, Baskaran S. J Org Chem 2018; 83: 1558-1564
- 10e Cecchi L, De Sarlo F, Machetti F. Eur J Org Chem 2006; 4852-4860
- 10f Cecchi L, De Sarloa F, Machetti F. Tetrahedron Lett 2005; 46: 7877-7879
- 10g Jen T, Mendelsohn BA, Ciufolini MA. J Org Chem 2011; 76: 728-731
- 10h Kacka-Zych A, Jasinski R. New J Chem 2021; 45: 9491-9500
- 10i Dai P, Tan X, Luo Q. et al. Org Lett 2019; 21: 5096-5100