Recent Advances in the Synthesis of Benzoheterocyclic Compounds Involving Isatins

doi:10.6023/cjoc202007034

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1527-1542.DOI: 10.6023/cjoc202007034 Previous Articles Next Articles

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靛红在苯并氮杂环类化合物的合成应用进展

贾丰成^a^,^*(), 罗娜^a, 徐程^b^,^*(), 吴安心^c

a 武汉工程大学化学与环境工程学院武汉 430205
b 湖北师范大学化学化工学院黄石 435002
c 华中师范大学化学学院武汉 430079

收稿日期:2020-07-12 修回日期:2020-10-01 发布日期:2020-10-28
通讯作者: 贾丰成, 徐程
基金资助:
国家自然科学基金(21901193); 湖北省自然科学基金(2018CFB149); 湖北省教育厅科学研究计划中青年人才(Q20181509); 武汉工程大学科学研究基金(K201834)

Recent Advances in the Synthesis of Benzoheterocyclic Compounds Involving Isatins

Fengcheng Jia^a^,^*(), Na Luo^a, Cheng Xu^b^,^*(), Anxin Wu^c

a School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073
b Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi 435002
c Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079

Received:2020-07-12 Revised:2020-10-01 Published:2020-10-28
Contact: Fengcheng Jia, Cheng Xu
About author:
* Corresponding authors. E-mail: jia@wit.edu.cn;
E-mail: chemxucheng@126.cn
Supported by:
National Natural Science Foundation of China(21901193); Natural Science Foundation of Hubei Province(2018CFB149); Young and Middle-Aged Talent Program of Hubei Provincial Department of Education(Q20181509); Science Foundation of Wuhan Institute of Technology(K201834)

Isatin is a natural small molecule compound of the indole class. Due to its unique structure, low cost and easy availability, the use of isatin as a starting material to construct complex and diverse heterocyclic compounds has been a research hotspot in the field of organic synthesis. Since isatin possess rich reaction sites, it has a significant step advantage in converting it into similar heterocycles. In recent years, the great progress has been made in the construction of heterocyclic compounds based on domino reactions involving isatins. According to the different types of heterocycles, the research progress in the synthesis of benzoheterocyclic compounds by the domino reactions related to isatins is briefly discussed.

Key words: isatins, domino reactions, benzoheterocyclic compounds, reaction mechanism

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Fengcheng Jia, Na Luo, Cheng Xu, Anxin Wu. Recent Advances in the Synthesis of Benzoheterocyclic Compounds Involving Isatins[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1527-1542.

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Fig. & Tab. 29

Scheme 1. Proposed mechanism of copper-catalyzed multicomponent reactions toward 3?functionalized oxindoles

Scheme 2. Proposed mechanism for the 1,3-dipolar cycloaddition/inverse 1,3-dipolar ring opening of isatins with isocyanoacetate

Scheme 3. Proposed mechanism for zinc-catalyzed alkyne- carbonyl metathesis of ynamides with isatins

Scheme 4. Proposed mechanism for Yb(OTf)3?catalyzed alkyne-carbonyl metathesis-oxa-michael addition relay

Scheme 5. Proposed mechanism for the cyclization of isatins with aniline derivatives

Scheme 6. Proposed mechanism for hydride transfer initiated ring expansion of pyrrolidines

Scheme 7. Proposed mechanism for palladium-catalyzed cross-coupling of isatins with alkynoates

Scheme 8. Proposed mechanism for Rh(II)-catalyzed denitrogenative reaction of isatins with N?Sulfonyl-1,2,3-triazoles

Scheme 9. Cyclization reaction of isatins with α-bro- moamide in the absence of transition metals

Scheme 10. Proposed mechanism for Rh(II)-catalyzed domino reaction of isatin tethered N-sulfonyl-1,2,3-triazoles and indoles

Scheme 11. Palladium-catalyzed oxidative cycloaddition of isatin and alkyne

Scheme 12. Proposed mechanism for domino reaction of isatins with heterocyclic ketene aminals

Scheme 13. Proposed mechanism for domino reaction of isatins with enaminones and carboxylic acids

Scheme 14. Proposed mechanism for domino reaction of isatins and enaminones

Scheme 15. Proposed mechanism for I2-triggered domino reaction of isatins and enaminones

Scheme 16. domino reaction of isatins and enaminones

Scheme 17. TBHP/K3PO4 promoted oxidative cyclization of isatins

Scheme 18. Proposed mechanism of TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted dimroth rearrangement

Scheme 19. Proposed mechanism for TBHP/TFA promoted oxidative cyclization of isatins with 1,2,3,4-tetrahydroisoquino-lines

Scheme 20. Proposed mechanism for O2-promoted domino reaction of isatins and o-phenylene diamines

Scheme 21. Proposed mechanism for copper-catalyzed domino reaction of isatins and enaminones

Scheme 22. Proposed mechanism for iron-catalyzed domino reaction of isatins and tri?uoroacetimidoyl chlorides

Scheme 23. Proposed mechanism of p-TSA-promoted three-component tandem cyclization

Scheme 24. Selective examples of active drug molecules containing 4-quinolone core

Scheme 25. TBHP/base promoted oxidative cyclization of isatins with alkynes

Scheme 26. TBHP/ K2CO3 promoted oxidative cyclization of isatins with 1,3-dicarbonyl compounds

Scheme 27. Sc(OTf)3 catalyzed ring-expansion reaction of isatins and diazoesters

Scheme 28. Proposed mechanism for copper-catalyzed decarboxylative coupling reactions of isatins with arylglyoxylic acids

Scheme 29. Proposed mechanism of Et3N-promoted three-component tandem cyclization

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靛红在苯并氮杂环类化合物的合成应用进展

Recent Advances in the Synthesis of Benzoheterocyclic Compounds Involving Isatins

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