α,β-不饱和硝酮的合成及其应用的研究进展

doi:10.6023/cjoc202109007

有机化学 ›› 2021, Vol. 41 ›› Issue (12): 4535-4553.DOI: 10.6023/cjoc202109007 上一篇下一篇

所属专题：绿色合成化学专辑；热点论文虚拟合集

综述与进展

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

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摘要/Abstract

在有机合成化学中, 硝酮作为有机合成中重要的1,3-偶极子, 由于其具有稳定性好、易合成和反应活性高等优点, 能够参与各种有机合成反应, 如氧转移反应、环加成反应、重排反应以及C—H键活化等, 可以用于合成各种各样的杂环化合物, 是进一步构建复杂分子的重要有机砌块. 近年来, α,β-不饱和硝酮由于其α,β-不饱和键具有较强的化学转化能力, 可以参与各种新型的化学转化合成结构新颖的杂环化合物, 从而引起了合成化学家的广泛关注. 综述了近十年来α,β-不饱和硝酮合成的新策略, 及其应用于构建各类骨架新颖的含氮杂环化合物, 包括氧转移反应、与亲核试剂或自由基的加成反应以及各种环加成反应.

关键词: α,β-不饱和硝酮, 环加成反应, 1,3-偶极子, 氮杂环化合物, 串联反应

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

引用此文

邹宁, 覃小婷, 王治新, 石维敏, 莫冬亮. α,β-不饱和硝酮的合成及其应用的研究进展[J]. 有机化学, 2021, 41(12): 4535-4553.

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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图/表 35

图1. 硝酮的类型

Figure 1. Type of nitrones

图式1. N-芳基-α,β-不饱和硝酮的合成

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

图式2. 通过肟N-芳基化反应合成N-芳基-α,β-不饱和硝酮

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

图式3. 有机胺催化氧化还原生成硝酮

Scheme 3. Amine-catalyzed nitrone formation via redox reaction

图式4. 1,3-烯炔的氢镁化合成α-炔基硝酮

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

图式5. Chan-Lam反应制备N-烯基-α,β不饱和硝酮

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

图式6. 铜催化2,3-重排合成N-烷基-α,β-不饱和硝酮

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

图式7. N-烷基-α,β-不饱和硝酮形成的反应机理

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

图式8. N-芳基-α,β-不饱和硝酮合成C(3)-季碳吲哚啉

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

图式9. N-苯基-α,β-不饱和硝酮合成C(3)-季碳吲哚啉的反应机理

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

图式10. N-芳基-α,β-不饱和硝酮合成吡咯并二氢吲哚

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

图式11. N-芳基-α,β-不饱和硝酮不对称构建二氢吡啶并吲哚化合物

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

图式12. 反式二氢吡啶并吲哚化合物的差向异构化

Scheme 12. Epimerization of cis-dihydropyridoinoldes

图式13. 级联策略构建2,3-季碳稠环吲哚啉

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

图式14. N-芳基-α,β-不饱和硝酮合成官能团化的吲哚化合物

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

图式15. N-芳基-α,β-不饱和硝酮合成官能团化的吲哚化合物

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

图式16. N-芳基-α,β-不饱和硝酮构建异噁唑啉化合物

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

图式17. 可见光促进的Chan-Lam偶联/[3+2]环加成反应

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

图式18. N-芳基-α,β-不饱和硝酮构建α,β-环氧酮亚胺

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

图式19. N-芳基-α,β-不饱和硝酮合成N-芳乙烯基脒

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

图式20. N-芳基-α,β-不饱和硝酮构建β-内酰胺化合物

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

图式21. N-芳基-α,β-不饱和硝酮构建双环四氢苯并氮杂酮

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

图式22. N-烯基-α,β-不饱和硝酮构建氮杂九元环化合物

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

图式23. N-烯基-α,β-不饱和硝酮构建氮杂九元环化合物

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

图式24. N-烯基-α,β-不饱和硝酮构建氮杂九元环化合物

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

图式25. N-烯基-α,β-不饱和硝酮通过可见光构建氮杂九元环化合物

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

图式26. N-烯基-α,β-不饱和硝酮通过可见光构建氮杂九元环过氧化合物的反应机理

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

图式27. 异噁唑啉及配体L1的合成

Scheme 27. Synthesis of isoxazolines and Ligand L1

图式28. 合成多取代吡啶和3,5-二取代异噁唑啉反应机理

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

图式29. N-烯基-α,β-不饱和硝酮构建γ-内酯化合物

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

图式30. N-烯基-α,β-不饱和硝酮构建γ-内酯反应机理

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

图式31. N-烯基-α,β-不饱和硝酮构建多取代稠环吡咯

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

图式32. N-烷基-α,β-不饱和硝酮构建噁嗪酮类化合物

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

图式33. N-烷基-α,β-不饱和硝酮构建噁嗪类化合物

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

图式34. 通过五元环状硝酮的1,3-偶极环加成构建异噁唑衍生物

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

参考文献 47

[1]	(a) Smith, L. L. Chem. Rev. 1938, 38, 193. pmid: 20111795
	(b) Bartoli, G.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1990, 55, 4456. doi: 10.1021/jo00301a046 pmid: 20111795
	(c) Braum, K. R.; Freysoldt, T. H. E.; Wierschem, F. Chem. Soc. Rev. 2005, 34, 507. doi: 10.1039/b311200b pmid: 20111795
	(d) Pellissier, H. Tetrahedron 2007, 63, 3235. doi: 10.1016/j.tet.2007.01.009 pmid: 20111795
	(e) Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247. doi: 10.1016/j.tet.2007.09.065 pmid: 20111795
	(f) Brandi, A.; Cardona, F.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem.-Eur. J. 2009, 15, 7808. doi: 10.1002/chem.v15:32 pmid: 20111795
	(g) Najera, C.; Sansano, J. M. Org. Biomol. Chem. 2009, 7, 4567. doi: 10.1039/b913066g pmid: 20111795
	(h) Kissane, M.; Maguire, A. R. Chem. Soc. Rev. 2010, 39, 845. doi: 10.1039/b909358n pmid: 20111795
[2]	(a) Saha, N.; Biswas, T.; Chattopadhyay, S. K. Org. Lett. 2011, 13, 5128. doi: 10.1021/ol2019967 pmid: 26376282
	(b) Hodges, A. J.; Adams, J. P.; Bond, A. D.; Holmes, A, B.; Press, N. J.; Roughley, S. D.; Ryan, J. H.; Saubern, S.; Smith, C. J.; Turnbull, M. D.; Newton, A. F. Org. Biomol. Chem. 2012, 10, 8963. pmid: 26376282
	(c) Martella, D.; Cardona, F.; Parmeggiani, C.; Franco, F.; Tamayo, J. A.; Robina, I.; Moreno-Clavijo, E.; Moreno-Vargas, A. J.; Goti, A. Eur. J. Org. Chem. 2013, 19, 4047. pmid: 26376282
	(d) Ideue, E.; Shimokawa, J.; Fukuyama, T. Org. Lett. 2015, 17, 4964. doi: 10.1021/acs.orglett.5b02373 pmid: 26376282
[3]	(a) Breslow, R. Angew. Chem., Int. Ed. 1968, 7, 565. doi: 10.1002/(ISSN)1521-3773 pmid: 26467943
	(b) Black, D. S. C.; Crozier, R. F.; Davis, V. C. Synthesis 1975, 205. pmid: 26467943
	(c) Claire, A. Future Med. Chem. 2012, 4, 9. doi: 10.4155/fmc.11.173 pmid: 26467943
	(d) Ma, L.-L.; Wang, W.; Wang, G.-C. RSC Adv. 2016, 6, 53839. doi: 10.1039/C6RA07873G pmid: 26467943
	(e) Clementson, S.; Radaelli, A.; Fjebye, K.; Tanner, D.; Jessing, M. Org. Lett. 2019, 21, 4763. doi: 10.1021/acs.orglett.9b01652 pmid: 26467943
	(f) Zhao, D.; Zhang, J.; Xie, Z. J. Am. Chem. Soc. 2015, 137, 13938. doi: 10.1021/jacs.5b09074 pmid: 26467943
[4]	(a) Zhou, Z.; Liu, G.; Chen, Y.; Lu, X. Adv. Synth. Catal. 2015, 357, 2944. doi: 10.1002/adsc.v357.13 pmid: 30047738
	(b) Wang, H.; Moselage, M.; Gonzalez, M. J.; Ackermann, L. ACS Catal. 2016, 6, 2705. doi: 10.1021/acscatal.5b02937 pmid: 30047738
	(c) Bai, D.; Jia, Q.; Xu, T.; Zhang, Q.; Wu, F.; Ma, C.; Liu, B.; Chang, J.; Li, X. J. Org. Chem. 2017, 82, 9877. doi: 10.1021/acs.joc.7b01574 pmid: 30047738
	(d) Pandey, A. K.; Kang, D.; Han, S. H.; Lee, H.; Mishra, N. K.; Kim, H. S.; Jung, Y. H.; Hong, S.; Kim, I. S. Org. Lett. 2018, 20, 4632. doi: 10.1021/acs.orglett.8b01910 pmid: 30047738
	(e) Li, Y.; Xie, F.; Liu, Y.; Yang, X.; Li, X. Org. Lett. 2018, 20, 437. doi: 10.1021/acs.orglett.7b03775 pmid: 30047738
	(f) Murahashi, S.-I.; Imada, Y. Chem. Rev. 2019, 119, 4684. doi: 10.1021/acs.chemrev.8b00476 pmid: 30047738
[5]	For some examples with alkenes, see: (a) Confalone, P. N.; Huie, E. M. Org. React. 2004, 36, 1. pmid: 25333970
	(b) Morita, N.; Fukui, K.; Irikuchi, J.; Sato, H.; Takano, Y.; Okamoto, I.; Ishibashi, H.; Tamura, O. J. Org. Chem. 2008, 73, 7164. doi: 10.1021/jo800878p pmid: 25333970
	(c) Nguyen, T. B.; Martel, A.; Dhal, R.; Dujardin, G. Org. Lett. 2008, 10, 4493. doi: 10.1021/ol8017243 pmid: 25333970
	(d) Bokach, N. A.; Kuznetsov, M. L.; Kukushkin, V. Y. Coord. Chem Rev. 2011, 255, 2946. doi: 10.1016/j.ccr.2011.07.001 pmid: 25333970
	(e) Lahiri, R.; Palanivel, A.; Kulkarni, S. A.; Vankar, Y. D. J. Org. Chem. 2014, 79, 10786. doi: 10.1021/jo5016745 pmid: 25333970
	(f) Kumar, C. V. S.; Ramana, C. V. Org. Lett. 2015, 17, 2870. doi: 10.1021/acs.orglett.5b00837 pmid: 25333970
	(g) Ghosh, A.; Mane, M. V.; Rode, H. B.; Patil, S. A.; Sridhar, B.; Dateer, R. B. Chem.-Asian. J. 2020, 15, 1. doi: 10.1002/asia.v15.1 pmid: 25333970
[6]	For some examples with alkynes, see: (a) Lu, C.; Dubrovskiy, A. V.; Larock, R. C. J. Org. Chem. 2012, 77, 2279. doi: 10.1021/jo2025064 pmid: 28862453
	(b) Bhunia, S.; Chang, C. J.; Liu, R. S. Org. Lett. 2012, 14, 5522. doi: 10.1021/ol302621z pmid: 28862453
	(c) Mckay, C. S.; Chigrinova, M.; Blake, J. A.; Peaccki, J. P. Org. Biomol. Chem. 2012, 10, 3066. doi: 10.1039/c2ob07165g pmid: 28862453
	(d) Zhang, Y. Q.; Zhang, J. L. Chem. Commun. 2012, 48, 4710. doi: 10.1039/c2cc30309d pmid: 28862453
	(e) Qi, Z. S.; Wang, M.; Li, X. W. Org. Lett. 2013, 15, 5440. doi: 10.1021/ol4025309 pmid: 28862453
	(f) Huehls, C. B.; Huang, J.; Yang, J. Tetrahedron 2015, 71, 3593. doi: 10.1016/j.tet.2015.02.069 pmid: 28862453
	(g) Huple, D. B.; Ghorpade, S.; Liu, R.-S. Adv. Synth. Catal. 2016, 358, 1348. doi: 10.1002/adsc.201600018 pmid: 28862453
	(i) Tangara, S.; Aupic, C.; Kanazawa, A.; Poisson, J.-F.; Py, S. Org. Lett. 2017, 19, 4842. doi: 10.1021/acs.orglett.7b02283 pmid: 28862453
	(h) Malig, T. C.; Yu, D.; Hein, J. E. J. Am. Chem. Soc. 2018, 140, 9167. doi: 10.1021/jacs.8b04635 pmid: 28862453
	(i) Zhang, G.; Alshreimi, A. S.; Alonso, L.; Antar, A.; Yu, H.-C.; Islan, S. M.; Anderson, L. L. Angew. Chem., Int. Ed. 2021, 60, 13089. doi: 10.1002/anie.v60.23 pmid: 28862453
[7]	(a) Malinina, J.; Tran, T. Q.; Stepakov, A. V.; Gurzhiy, V. V.; Starova, G. L.; Kostikov, R. R.; Molchanov, A. P. Tetrahedron Lett. 2014, 55, 3663. doi: 10.1016/j.tetlet.2014.04.107 pmid: 27682854
	(b) Anderson, L. L.; Kroc, M. A.; Reidl, T. W.; Son, J J. Org. Chem. 2016, 81, 9521. pmid: 27682854
	(c) Lee, W.; Yuan, M.; Ashley, C.; Onwu, A.; Gutierrez, O. Org. Biomol. Chem. 2019, 17, 1767. doi: 10.1039/C8OB02346H pmid: 27682854
[8]	(a) Namitharan, K.; Pitchumani, K. Org. Lett. 2011, 13, 5278. doi: 10.1021/ol202080x
	(b) Qin, C.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 14516. doi: 10.1021/ja4069003
	(c) Wozniak, L.; Krajewska, O. S.; Michalak, M. Chem. Commun. 2015, 51, 1933. doi: 10.1039/C4CC08742A
[9]	(a) Bartoli, G.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1990, 55, 4456. doi: 10.1021/jo00301a046 pmid: 16872207
	(b) Denmark, S. E.; Montgomery, J. I. J. Org. Chem. 2006, 71, 6211. pmid: 16872207
	(c) Yang, J. Synlett 2012, 23, 2293. doi: 10.1055/s-00000083 pmid: 16872207
[10]	(a) Shi, W.-M.; Ma, X.-P.; Su, G.-F.; Mo, D.-L. Org. Chem. Front. 2016, 3, 116. doi: 10.1039/C5QO00122F pmid: 28327748
	(b) Anderson, L. L. Asian J. Org. Chem. 2016, 5, 9. doi: 10.1002/ajoc.201500211 pmid: 28327748
	(c) Merino, P.; Tejero, T.; Delso, I.; Matute, R. Org. Biomol. Chem. 2017, 15, 3364. doi: 10.1039/c7ob00429j pmid: 28327748
	(d) Murahashi, S.-I.; Imada, Y. Chem. Rev. 2019, 119, 4684. doi: 10.1021/acs.chemrev.8b00476 pmid: 28327748
	(e) Sukhorukov, A. Y. Adv. Synth. Catal. 2020, 362, 724. doi: 10.1002/adsc.201900718 pmid: 28327748
	(f) Thakur, S.; Das, A.; Das, T. New J. Chem. 2021, 45, 11420. doi: 10.1039/D1NJ02023D pmid: 28327748
	(g) Wang, L.; Zhang, Z.; Han, H.; Liu, X.; Bu, Z.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 12. (in Chinese) doi: 10.6023/cjoc202007045 pmid: 28327748
	( 王乐乐, 张子莹, 韩华彬, 刘雄利, 卜站伟, 王琪琳, 有机化学, 2021, 41, 12.) doi: 10.6023/cjoc202007045 pmid: 28327748
[11]	(a) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1.
	(b) Soldaini, G.; Cardona, F.; Goti, A. Org. Lett. 2007, 9, 473. doi: 10.1021/ol062862w
	(c) Gella, C.; Ferrer, E.; Alibes, R.; Busque, F.; de March, P.; Figueredo, M.; Font, J. J. Org. Chem. 2009, 74, 6365. doi: 10.1021/jo901108u
	(d) Hota, S. K.; Chatterjee, A.; Bhattacharya, P. K.; Chattopadhyay, P. Green Chem. 2009, 11, 169. doi: 10.1039/B812290C
	(e) Forcato, M.; Mba, M.; Nugent, W. A.; Licini, G. Eur. J. Org. Chem. 2010, 740.
	(f) Abrantes, M.; Goncalves, I. S.; Pillinger, M.; Vurchio, C.; Cordero, F. M.; Brandi, A. Tetrahedron Lett. 2011, 52, 7079. doi: 10.1016/j.tetlet.2011.10.079
	(g) Zhang, Y. H.; Wu, M. Y.; Huang, W. C. RSC Adv. 2015, 5, 105825. doi: 10.1039/C5RA21874H
[12]	Hood, T. S.; Huehls, C. B.; Yang, J. Tetrahedron Lett. 2012, 53, 4679. doi: 10.1016/j.tetlet.2012.06.083
[13]	Ma, X.-P.; Shi, W.-M.; Mo, X.-L.; Li, X.-H.; Li, L.-G.; Pan, C.-X.; Chen, B.; Su, G.-F.; Mo, D.-L. J. Org. Chem. 2015, 80, 10098. doi: 10.1021/acs.joc.5b01716
[14]	Fraboni, A. J.; Brenner-Moyer, S. E. Org. Lett. 2016, 18, 2146. doi: 10.1021/acs.orglett.6b00770
[15]	Li, Y.; Ng, J. S.; Wang, B.; Chiba, S. Org. Lett. 2021, 23, 5060. doi: 10.1021/acs.orglett.1c01583
[16]	(a) Ma, X.-P.; Liu, F.-P.; Mo, D.-L. Chin. J. Org. Chem. 2017, 37, 1069. (in Chinese) doi: 10.6023/cjoc201702001
	( 马小盼, 刘凤萍, 莫冬亮, 有机化学, 2017, 37, 1069.) doi: 10.6023/cjoc201702001
	(b) Chen, J.-Q.; Li, J.-H.; Dong, Z.-B. Adv. Synth. Catal. 2020, 362, 3311. doi: 10.1002/adsc.v362.16
[17]	(a) Mo, D.-L.; Wink, D. A.; Anderson, L. L. Org. Lett. 2012, 14, 5180. doi: 10.1021/ol3022885
	(b) Chen, C.-H.; Liu, Q.-Q.; Ma, X.-P.; Feng, Y.; Liang, C.; Pan, C.-X.; Su, G.-F.; Mo, D.-L. J. Org. Chem. 2017, 82, 6417. doi: 10.1021/acs.joc.7b00620
	(c) Mo, X.-L.; Chen, C.-H.; Liang, C.; Mo, D.-L. Eur. J. Org. Chem. 2018, 2018, 150. doi: 10.1002/ejoc.v2018.2
[18]	Kontokosta, D.; Mueller, D. S.; Mo, D.-L.; Pace, W. H.; Simpson, R. A.; Anderson, L. L. Beilstein J. Org. Chem. 2015, 11, 2097. doi: 10.3762/bjoc.11.226 pmid: 26664630
[19]	Nakamura, I.; Onuma, T.; Kanazawa, R.; Nishigai, Y.; Terada, M. Org. Lett. 2014, 16, 4198. doi: 10.1021/ol501889g pmid: 25058679
[20]	Li, X.; Yan, W.; Zhang, R.; Chang, H.; Gao, W.; Tian, X.; Wei, W. Synthesis 2019, 51, 4043. doi: 10.1055/s-0039-1690186
[21]	Nakamura, I.; Okamoto, M.; Sato, Y.; Terada, M. Angew. Chem., Int. Ed. 2012, 51, 10816. doi: 10.1002/anie.v51.43
[22]	Nakamura, I.; Sato, Y.; Takeda, K.; Terada, M. Chem.-Eur. J. 2014, 20, 10214. doi: 10.1002/chem.201403637 pmid: 25044489
[23]	Chen, F.; Yang, X.-L.; Wu, Z.-W.; Han, B. J. Org. Chem. 2016, 81, 3042. doi: 10.1021/acs.joc.6b00180 pmid: 26954339
[24]	Huehls, C. B.; Hood, T. S.; Yang, J. Angew. Chem., Int. Ed. 2012, 51, 5110. doi: 10.1002/anie.201200860
[25]	Mo, D.-L.; Wink, D. J.; Anderson, L. L. Chem.-Eur. J. 2014, 20, 13217. doi: 10.1002/chem.201403268
[26]	Huehls, C. B.; Huang, J.; Yang, J. Tetrahedron 2015, 71, 3593. doi: 10.1016/j.tet.2015.02.069
[27]	Pace, W. H.; Mo, D.-L.; Reidl, T. W.; Wink, D. J.; Anderson, L. L. Angew. Chem., Int. Ed. 2016, 55, 9183. doi: 10.1002/anie.v55.32
[28]	Ma, X.-P.; Li, K.; Wu, S.-Y.; Liang, C.; Su, G.-F.; Mo, D.-L. Green. Chem. 2017, 19, 5761. doi: 10.1039/C7GC02844J
[29]	Kroc, M. A.; Prajapati, A.; Wink, D. J.; Anderson, L. L. J. Org. Chem. 2018, 83, 1085. doi: 10.1021/acs.joc.7b02638
[30]	Xu, P.-P.; Liao, J.-Y.; Zhang, J.-J.; Shi, W.-M.; Liang, C.; Su, G.-F.; Mo, D.-L. Org. Lett. 2021, 23, 7482. doi: 10.1021/acs.orglett.1c02695
[31]	Ghosh, A.; Mane, M. V.; Rode, H. B.; Patil, S. A.; Sridhar, B.; Dateer, R. B. Chem.-Asian. J. 2020, 15, 899. doi: 10.1002/asia.v15.6
[32]	Zhao, J.; Huang, B.-Q.; Zhu, B.-C.; Ma, X.-P.; Mo, D.-L. Adv. Synth. Catal. 2021, 363, 4575. doi: 10.1002/adsc.v363.19
[33]	Mo, D.-L.; Anderson, L. L. Angew. Chem., Int. Ed. 2013, 52, 6722. doi: 10.1002/anie.v52.26
[34]	Mo, D.-L.; Pecak, W. H.; Zhao, M.; Wink, D. J.; Anderson, L. L. Org. Lett. 2014, 16, 3696. doi: 10.1021/ol501503a
[35]	Kumar, Y.; Singh, P.; Bhargave, G. New J. Chem. 2016, 40, 8216. doi: 10.1039/C6NJ01747A
[36]	Kroc, M. A.; Markiewicz, M.; Pace, W. H.; Wink, D. J.; Anderson, L. L. Chem. Commun. 2019, 55, 2309. doi: 10.1039/C8CC10313E
[37]	Zou, N.; Jiao, J.-W.; Feng, Y.; Chen, C.-H.; Liang, C.; Su, G.-F.; Mo, D.-L. Adv. Synth. Catal. 2017, 359, 3545. doi: 10.1002/adsc.v359.20
[38]	Ma, X.-P.; Li, L.-G.; Zhao, H.-P.; Du, M.; Liang, C.; Mo, D.-L. Org. Lett. 2018, 20, 4571. doi: 10.1021/acs.orglett.8b01761
[39]	Ma, X.-P.; Nong, C.-M.; Zhao, J.; Lu, X.; Liang, C.; Mo, D.-L. Adv. Synth. Catal. 2020, 6, 478.
[40]	Ma, X.-P.; Nong, C.-M.; Liang, Y.-F.; Xu, P.-P.; Guo, X.-Y.; Liang, C.; Pan, C.-X.; Su, G.-F.; Mo, D.-L. Green Chem. 2020, 22, 3827. doi: 10.1039/D0GC00929F
[41]	Chen, C.-H.; Wu, Q.-Y.; Wei, C.; Liang, C.; Su, G.-F.; Mo, D.-L. Green Chem. 2018, 20, 2722. doi: 10.1039/C8GC00630J
[42]	Liao, J.-Y.; Wu, Q.-Y.; Lu, X.; Zou, N.; Pan, C.-X.; Liang, C.; Su, G.-F.; Mo, D.-L. Green Chem. 2019, 21, 6567. doi: 10.1039/C9GC01811E
[43]	Zou, N.; Lan, J.-X.; Yan, G.-G.; Liang, C.; Su, G.-F.; Mo, D.-L. Org. Lett. 2020, 22, 8446. doi: 10.1021/acs.orglett.0c02947
[44]	Zou, N.; Jiao, J.-W.; Feng, Y.; Pan, C.-X.; Liang, C.; Su, G.-F.; Mo, D.-L. Org. Lett. 2019, 21, 481. doi: 10.1021/acs.orglett.8b03767
[45]	Jia, Q.; Li, D.; Lang, M.; Zhang, K.; Wang, J. Adv. Synth. Catal. 2017, 359, 3837. doi: 10.1002/adsc.v359.21
[46]	Hasegawa, M.; Suga, T.; Soeta, T.; Ukaji, Y. J. Org. Chem. 2020, 85, 11258. doi: 10.1021/acs.joc.0c01349 pmid: 32786638
[47]	Buchlovic, M.; Hebanova, S.; Potacek, M. Tetrahedron 2012, 68, 3117. doi: 10.1016/j.tet.2012.01.043

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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