Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

doi:10.6023/cjoc202109007

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4535-4553.DOI: 10.6023/cjoc202109007 Previous Articles Next Articles

Special Issue: 绿色合成化学专辑；热点论文虚拟合集

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α,β-不饱和硝酮的合成及其应用的研究进展

邹宁^a, 覃小婷^a, 王治新^a, 石维敏^b^,^*(), 莫冬亮^a^,^*()

a 广西师范大学化学与药学学院省部共建药用资源化学与药物分子工程国家重点实验室广西桂林 541004
b 广西科技大学医学部药学系广西柳州 545006

收稿日期:2021-09-03 修回日期:2021-10-30 发布日期:2021-11-09
通讯作者: 石维敏, 莫冬亮
基金资助:
国家自然科学基金(21871062); 国家自然科学基金(22071035); 广西省自然科学基金(2018GXNSFAA281329); 广西教育厅研究生创新计划(YCBZ2021039); 广西高校千名中青年骨干教师培育计划资助项目

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

Ning Zou^a, Xiaoting Qin^a, Zhixin Wang^a, Weimin Shi^b(), Dongliang Mo^a()

a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004
b School of Medicine, Guangxi University of Science and Technology, Liuzhou, Guangxi 545006

Received:2021-09-03 Revised:2021-10-30 Published:2021-11-09
Contact: Weimin Shi, Dongliang Mo
Supported by:
National Natural Science Foundation of China(21871062); National Natural Science Foundation of China(22071035); Natural Science Foundation of Guangxi Province(2018GXNSFAA281329); Graduate Innovation Project of Guangxi Education(YCBZ2021039); “One thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program” of Guangxi

Nitrones, served as one of the most important 1,3-dipoles in organic synthetic chemistry, can participate in various organic synthetic reactions to synthesize various heterocyclic compounds, such as nucleophilic addition, cycloaddition reaction, rearrangement reaction, C—H bond activation, etc. They are very important organic building blocks for the further construction of complex molecules. In recent years, α,β-unsaturated nitrone has attracted widespread attention from synthetic chemists because of its α,β-unsaturated bond containing rich chemical transformations, and can take part in various new chemical conversions to construct new structural heterocyclic compounds. The new strategies for the preparation of α,β-unsaturated nitrones in the past ten years, and their applications to construct nitrogen heterocyclic compounds, including O-transfer reaction, addition of nucleophiles and radical reagents, and various cycloaddition reactions, are reviewed.

Key words: α,β-unsaturated nitrone, cycloaddition reaction, 1,3-dipole, N-heterocyclic compound, cascade reaction

Cite this article

Ning Zou, Xiaoting Qin, Zhixin Wang, Weimin Shi, Dongliang Mo. Advances on the Synthesis and Application of α,β-Unsaturated Nitrones[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4535-4553.

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Fig. & Tab. 35

Figure 1. Type of nitrones

Scheme 1. Synthesis of N-aryl-α,β-unsaturated nitrones

Scheme 2. Preparation of N-aryl-α,β-unsaturated nitrones through N-arylation of oximes

Scheme 3. Amine-catalyzed nitrone formation via redox reaction

Scheme 4. Synthesis of α-alkynylnitrones via hydromagnesiation of 1,3-enynes

Scheme 5. Preparation of N-vinyl-α,β-unsaturated nitrone via Chan-Lam reaction

Scheme 6. Synthesis of N-alkyl-α,β-unsaturated nitrones via Cu-catalyzed 2,3-rearrangement

Scheme 7. Proposed mechanism of forming N-alkyl-α,β- unsaturated nitrones

Scheme 8. Synthesis of C(3)-quaternary indolenine from N-aryl- α,β-unsaturated nitrones

Scheme 9. Possible mechanism of forming C(3)-quaternary indolenines from N-phenyl-α,β-unsaturated nitrones

Scheme 10. Synthesis of pyrroloindolines from N-aryl-α,β- unsaturated nitrones

Scheme 11. Asymmetric synthesis of trans-dihydropyridoindoles from N-aryl-α,β-unsaturated nitrone

Scheme 12. Epimerization of cis-dihydropyridoinoldes

Scheme 13. A cascade strategy for the construction of 2,3-quaternary fused indolines

Scheme 14. Synthesis of functionalized indoles from N-aryl-α,β-unsaturated nitrone

Scheme 15. Synthesis of functionalized indoles from N-aryl-α,β-unsaturated nitrone

Scheme 16. Construction of isoxazolidines from N-aryl-α,β- unsaturated nitrones

Scheme 17. Visible light promoted Chan-Lam reaction and [3+2] cycloaddition

Scheme 18. Preparation α,β-epoxyketimines from N-aryl-α,β- unsaturated nitrones

Scheme 19. Synthesis of N-styryl amidines from N-aryl-α,β-unsaturated nitrones

Scheme 20. Synthesis of β-lactams from N-aryl-α,β-unsaturated nitrones

Scheme 21. Construction of bicyclic tetrahydrobenzoazepines from N-aryl-α,β-unsaturated nitrones

Scheme 22. Synthesis of nine-membered heterocycles from N-vinyl-α,β-unsaturated nitrones

Scheme 23. Construction of nine-membered heterocycles from N-vinyl-α,β-unsaturated nitrones

Scheme 24. Construction of nine-membered heterocycles from N-vinyl-α,β-unsaturated nitrones

Scheme 25. Construction of nine-membered heterocycles from N-vinyl-α,β-unsaturated nitrones through visible light

Scheme 26. Proposed mechanism of constructing nine-membered heterocycles endoperoxides from N-vinyl-α,β-unsaturated nitrones through visible light

Scheme 27. Synthesis of isoxazolines and Ligand L1

Scheme 28. Reaction mechanism of synthesis of polysubstituted pyridine and 3,5-disubstituted isoxazoline

Scheme 29. Construction of γ-lactones from N-vinyl-α,β-unsaturated nitrones

Scheme 30. Proposed mechanism of constructing γ-lactones from N-vinyl-α,β-unsaturated nitrones

Scheme 31. Synthesis of polysubstituted pyrrolizines from N-vinyl-α,β-unsaturated nitrones

Scheme 32. Construction of oxazinones from N-alkyl-α,β-unsaturated nitrones

Scheme 33. Construction of oxazines from N-alkyl-α,β-unsaturated nitrones

Scheme 34. Construction of isoxazole derivatives by 1,3-dipolar cycloadditions of five-membered cyclic nitrones

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α,β-不饱和硝酮的合成及其应用的研究进展

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

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