靛红在苯并氮杂环类化合物的合成应用进展

doi:10.6023/cjoc202007034

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1527-1542.DOI: 10.6023/cjoc202007034 上一篇下一篇

综述与进展

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)

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摘要/Abstract

靛红是一种吲哚系天然小分子化合物, 由于其结构独特、廉价易得, 利用靛红作为起始原料来构建结构复杂多样的杂环化合物一直是有机合成领域的研究热点. 由于靛红具有丰富的反应位点, 在转化为类似的“近亲”杂环方面具有显著的步骤优势. 近年来基于靛红的串联反应构建杂环化合物方面研究取得了诸多进展. 根据合成杂环种类的不同, 对靛红参与的串联反应合成苯并杂环化合物的研究进展进行了简要论述.

关键词: 靛红, 串联反应, 苯并杂环化合物, 反应机理

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

引用此文

贾丰成, 罗娜, 徐程, 吴安心. 靛红在苯并氮杂环类化合物的合成应用进展[J]. 有机化学, 2021, 41(4): 1527-1542.

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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图/表 29

图式1. 铜催化合成3-官能团化吲哚酮多组分反应的可能机理

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

图式2. 靛红与异腈酸酯1,3-偶极环加成/反1,3-偶极开环的可能机理

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

图式3. 锌催化靛红的羰基与炔酰胺-炔基复分解反应的可能机理

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

图式4. Yb(OTf)3催化羰基-炔基复分解/氧杂迈克尔加成的可能机理

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

图式5. 靛红和苯胺衍生物环合反应的可能机理

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

图式6. 氢转移启动的吡咯扩环反应的可能机理

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

图式7. 钯催化的靛红C2羰基与炔酯交叉偶联反应的可能机理

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

图式8. 铑催化的靛红C2羰基与N-磺酰-1,2,3-三氮唑脱氮反应的可能机理

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

图式9. 无过渡金属条件下靛红C2羰基与α-溴代酰胺的环化反应

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

图式10. 铑催化的连有N-磺酰-1,2,3-三氮唑靛红与吲哚串联反应的可能机理

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

图式11. 钯催化的靛红与炔的氧化环加成反应

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

图式12. 靛红与乙烯酮缩二胺参与的串联反应的可能机理

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

图式13. 靛红与烯胺酮、羧酸参与的串联反应的可能机理

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

图式14. 靛红和烯胺酮参与的串联反应的可能机理

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

图式15. 碘引发的靛红和肟酯参与的串联反应的可能机理

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

图式16. 靛红和烯胺酮参与的串联反应

Scheme 16. domino reaction of isatins and enaminones

图式17. TBHP/K3PO4促进的与靛红有关的串联反应

Scheme 17. TBHP/K3PO4 promoted oxidative cyclization of isatins

图式18. TBHP/Na2CO3促进的串联氧化环化/中断Dimroth重排反应机理

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

图式19. TBHP/TFA促进的靛红和四氢异喹啉参与的氧化环化反应机理

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

图式20. 氧气促进的靛红和邻苯二胺参与的串联反应的可能机理

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

图式21. 铜催化的靛红和2-溴吡啶参与的串联反应的可能机理

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

图式22. 铜催化的靛红和三氟乙酰亚氨基酰氯参与的串联反应的可能机理

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

图式23. p-TSA促进的三组分串联环化反应机理

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

图式24. 含有4-喹诺酮核心结构的活性药物分子示例

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

图式25. TBHP/碱促进的靛红和炔参与的氧化环化反应

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

图式26. TBHP/K2CO3促进的靛红和1,3二羰基化合物参与的氧化环化反应

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

图式27. Sc(OTf)3催化的靛红和重氮酯参与的扩环反应

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

图式28. 铜催化的靛红和芳基酮酸参与的脱羧偶联反应机理

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

图式29. Et3N促进的三组分串联环化反应机理

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

参考文献 41

[1]	(a) Silva, J.; Garden, S.; Pinto, A. J. Braz. Chem. Soc. 2001, 12,273.
	(b) Bergman, J.; Lindström, J.O. Tetrahedron 1985, 41,2879.
[2]	(a) Raj, A.; Raghunathan, R.; Sridevikumaria, M.R.; Raman, N. Bioorg. Med. Chem. 2003, 11,407. pmid: 20696500
	(b) Tripathy, R.; Reiboldt, A.; Messina, P.; Iqbal, M.; Singh, J.; Bacon, E.; Angeles, T.; Yang, S.; Albom, M.; Robinson, C.; Chang, H.; Ruggeri, B.; Mallamo, J. Bioorg. Med. Chem. Lett. 2006, 16,2158. doi: 10.1016/j.bmcl.2006.01.063 pmid: 20696500
	(c) Jiang, T.; Kuhen, K.; Wolff, K.; Yin, H.; Bieza, K.; Caldwell, J.; Bursulaya, B.; Tuntland, T.; Zhang, K.; Karanewsky, D.; He, Y. Bioorg. Med. Chem. Lett. 2006, 16,2109. pmid: 20696500
	(d) Bal, T.; Anand, B.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2005, 15,4451. doi: 10.1016/j.bmcl.2005.07.046 pmid: 20696500
	(e) Aboul-Fadl, T.; Bin-Jubair, F.; Aboul-Wafa, O. Eur. J. Med. Chem. 2010, 45,4578. doi: 10.1016/j.ejmech.2010.07.020 pmid: 20696500
[3]	(a) Marti, C.; Carreira, E.M. J. Am. Chem. Soc. 2005, 127,11505. doi: 10.1021/ja0518880 pmid: 16599614
	(b) Mitsunuma, H.; Shibasaki, M.; Kanai, M.; Matsunaga, S. Angew. Chem. Int. Ed. 2012, 51,5217. pmid: 16599614
	(c) Hodges, T.R.; Benjamin, N.M.; Martin, S.F. Org. Lett. 2017, 19,2254. doi: 10.1021/acs.orglett.7b00735 pmid: 16599614
	(d) Wu, H.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132,14052. pmid: 16599614
	(e) Hughes, C.C.; Fenical, W. J. Am. Chem. Soc. 2010, 132,2528. pmid: 16599614
	(f) Sun, C.; Lin, X.; Weinreb, S.M. J. Org. Chem. 2006, 71,3159. doi: 10.1021/jo060084f pmid: 16599614
[4]	(a) Kumar, V.; Poonam; Prasad, A.K.; Parmar, V.S. Nat. Prod. Rep. 2003, 20,565. doi: 10.1039/b303648k pmid: 14700200
	(b) Bentley, K.W. Nat. Prod. Rep. 2006, 23,444. pmid: 14700200
[5]	(a) Liu, Y, H. Liaoning Med. 2002, (4),18. (in Chinese) pmid: 18625562
	( 刘英华, 辽宁医药, 2002, (4),18.) pmid: 18625562
	(b) Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J. A., R.P.; Dayam, R.; Neamati, N. J. Med. Chem. 2008, 51,3367. pmid: 18625562
	(c) Mendes da Silva, J.F.; Walters, M.; Al-Damluji, S.; Ganellin, C.R. Bioorg. Med. Chem. 2008, 16,7254. doi: 10.1016/j.bmc.2008.06.037 pmid: 18625562
[6]	(a) Ma, Z.Z.; Hano, Y.; Nomura, T.; Chen, Y.J. Heterocycles 1997, 46,541. pmid: 20251439
	(b) Michael, J.P. Nat. Prod. Rep. 2007, 24,223. doi: 10.1039/b509528j pmid: 20251439
	(c) Koepfli, J.B.; Mead, J.F.; Brockman, J. A. J. Am. Chem. Soc. 1947, 69,1837. doi: 10.1021/ja01199a513 pmid: 20251439
	(d) Koepfli, J.B.; Mead, J.F.; Brockman, J. A. J. Am. Chem. Soc. 1949, 71,1048. pmid: 20251439
	(e) Ablondi, F.; Gordon, S.; Morton, J.II, Williams, J.H. J. Org. Chem. 1952, 17,14. pmid: 20251439
[7]	Manfroni, G.; Cannalire, R.; Barreca, M.L.; Kaushik-Basu, N.; Leyssen, P.; Winquist, J.; Iraci, N.; Manvar, D.; Paeshuyse, J.; Guhamazumder, R.; Basu, A.; Sabatini, S.; Tabarrini, O.; Danielson, U.H.; Neyts, J.; Cecchetti, V. J. Med. Chem. 2014, 57,1952. pmid: 24131104
[8]	(a) Yang, Z.; Huang, D.; Wen, L.; Wang, J.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2018, 38,1725. (in Chinese) pmid: 22950860
	( 杨政, 黄丹凤, 文岚, 王娟娟, 王克虎, 胡雨来, 有机化学, 2018, 38,1725.) pmid: 22950860
	(b) Yang, F.; Sun, J.; Gao, H.; Yan, C.G. RSC Adv. 2015, 5,32786. pmid: 22950860
	(c) Singh, G.S.; Desta, Z.Y. Chem. Rev. 2012, 112,6104. doi: 10.1021/cr300135y pmid: 22950860
	(d) Liu, Y.; Wang, H.; Wan, J. Asian J. Org. Chem. 2013, 2,374. pmid: 22950860
	(e) Varun, V.; Sonam, S.; Kakkar, R. Med. Chem. Commun. 2019, 10,351. pmid: 22950860
[9]	Cheng, D.; Ling, F.; Zheng, C.; Ma, C. Org. Lett. 2016, 18,2435. doi: 10.1021/acs.orglett.6b00964 pmid: 27149101
[10]	Yuan, W.K.; Cui, T.; Liu, W.; Wen, L.R.; Li, M. Org. Lett. 2018, 20,1513. doi: 10.1021/acs.orglett.8b00217 pmid: 29517237
[11]	Ao, C.; Yang, X.; Jia, S.; Xu, X.; Yuan, Y.; Zhang, D.; Hu, W. J. Org. Chem. 2019, 84,15331. doi: 10.1021/acs.joc.9b02350 pmid: 31702914
[12]	Xu, T.; Chen, K.; Zhu, H.Y.; Hao, W.J.; Tu, S.J.; Jiang, B. Org. Lett. 2020, 22,2414. pmid: 32148050
[13]	Ramakumar, K.; Maji, T.; Partridge, J.J.; Tunge, J.A. Org. Lett. 2017, 19,4014. doi: 10.1021/acs.orglett.7b01752 pmid: 28737400
[14]	(a) Zhu, S.; Chen, C.; Duan, K.; Sun, Y.M.; Li, S.S.; Liu, Q.; Xiao, J. J. Org. Chem. 2019, 84,8440. pmid: 30721075
	(b) Li, S.S.; Zhu, S.; Chen, C.; Duan, K.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21,1058. pmid: 30721075
	(c) Wang, S.; An, X.D.; Li, S.S.; Liu, X.; Liu, Q.; Xiao, J. Chem. Commun. 2018, 54,13833. pmid: 30721075
[15]	Wang, L.; Du, Z.; Peng, S.; Zhang, K.; Wang, J. Adv. Synth. Catal. 2014, 356,2943.
[16]	Pal, K.; Shukla, R.K.; Volla, C.M. R. Org. Lett. 2017, 19,5764. doi: 10.1021/acs.orglett.7b02697 pmid: 29058439
[17]	Jiang, S.; Li, K.; Yan, J.; Shi, K.; Zhao, C.; Yang, L.; Zhong, G. J. Org. Chem. 2017, 82,9779. doi: 10.1021/acs.joc.7b00547 pmid: 28829132
[18]	(a) Mei, G.J.; Bian, C.Y.; Li, G.H.; Xu, S.L.; Zheng, W.Q.; Shi, F. Org. Lett. 2017, 19,3219. pmid: 30023685
	(b) Jiang, K.M.; Luesakul, U.; Zhao, S.Y.; An, K.; Muangsin, N.; Neamati, N.; Jin, Y.; Lin, J. ACS Omega 2017, 2,3123. doi: 10.1021/acsomega.7b00490 pmid: 30023685
[19]	Kahar, N.; Jadhav, P.; Reddy, R.V. R.; Dawande, S. Chem. Commun. 2020, 56,1207.
[20]	Wang, L.; Huang, J.; Peng, S.; Liu, H.; Jiang, X.; Wang, J. Angew. Chem. Int. Ed. 2012, 52,1768.
[21]	(a) Pfitzinger, W. J. Prak. Chem. 1886, 33,100.
	(b) Zhu, H.; Yang, R.F.; Yun, L.H.; Li, J. Chin. Chem. Lett. 2010, 21,35.
[22]	(a) Yu, F.; Yan, S.; Hu, L.; Wang, Y.; Lin, J. Org. Lett. 2011, 13,4782. pmid: 21848302
	(b) Xu, H.; Zhou, B.; Zhou, P.; Zhou, J.; Shen, Y.; Yu, F.C.; Lu, L.L. Chem. Commun. 2016, 52,8002. pmid: 21848302
[23]	(a) Wang, H.; Li, L.; Lin, W.; Xu, P.; Huang, Z.; Shi, D. Org. Lett. 2012, 14,4598. doi: 10.1021/ol302058g pmid: 22920713
	(b) Hao, W.J.; Wang, J.Q.; Xu, X.P.; Zhang, S.L.; Wang, S.Y.; Ji, S.J. J. Org. Chem. 2013, 78,12362. pmid: 22920713
[24]	(a) Gao, Q.; Liu, Z.; Wang, Y.; Wu, X.; Zhang, J.; Wu, A. Adv. Synth. Catal. 2018, 360,1364.
	(b) Ramaraju, A.; Chouhan, N.K.; Ravi, O.; Sridhar, B.; Bathula, S.R. Eur. J. Org. Chem. 2018,2963.
[25]	Wang, B.Q.; Zhang, C.H.; Tian, X.X.; Lin, J.; Yan, S.J. Org. Lett. 2018, 20,660. pmid: 29323495
[26]	(a) Mhaske, S.B.; Argade, N.P. Tetrahedron 2006, 62,9787. pmid: 25147608
	(b) Lee, S.; Son, J.K.; Jeong, B.; Jeong, T.C.; Chang, H.; Lee, E.S.; Jahng, Y. Molecules 2008, 13,272. doi: 10.3390/molecules13020272 pmid: 25147608
	(c) D'yakonov, A.L.; Telezhenetskaya, M.V. Chem. Nat. Compd. 1997, 33,221. pmid: 25147608
	(d) Michael, J.P. Nat. Prod. Rep. 2008, 25,166. doi: 10.1039/b612168n pmid: 25147608
	(e) Fang, J.; Zhou, J. Org. Biomol. Chem. 2012, 10,2389. doi: 10.1039/c2ob07178a pmid: 25147608
	(f) Li, Y.; Feng, T.; Liu, P.; Liu, C.; Wang, X.; Li, D.; Li, N.; Chen, M.; Xu, Y.; Si, S. ACS Med. Chem. Lett. 2014, 5,884. pmid: 25147608
	(g) Liang, J.L.; Cha, H.C.; Jahng, Y. Molecules 2011, 16,4861. pmid: 25147608
[27]	Jia, F.C.; Zhou, Z.W.; Xu, C.; Wu, Y.D.; Wu, A.X. Org. Lett. 2016, 18,2942.
[28]	Zhou, Z.W.; Jia, F.C.; Xu, C.; Jiang, S.F.; Wu, Y.D.; Wu, A.X. Chem. Commun. 2017, 53,1056.
[29]	Jia, F.C.; Chen, T.Z.; Hu, X.Q. Org. Chem. Front. 2020, 7,1635.
[30]	Li, P.G.; Yan, C.; Zhu, S.; Liu, S.H.; Zou, L.H. Org. Chem. Front. 2018, 5,3464.
[31]	Liu, M.; Shu, M.; Yao, C.; Yin, G.; Wang, D.; Huang, J. Org. Lett. 2016, 18,824.
[32]	Wang, L.C.; Du, S.; Chen, Z.; Wu, X.F. Org. Lett. 2020, 22,5567. pmid: 32610908
[33]	Balwe, S.G.; Jeong, Y.T. Org. Chem. Front. 2018, 5,1628.
[34]	(a) Manfroni, G.; Cannalire, R.; Barreca, M. L.; Kaushik-Basu, N.; Leyssen, P.; Winquist, J.; Iraci, N.; Manvar, D.; Paeshuyse, J.; Guhamazumder, R.; Basu, A.; Sabatini, S.; Tabarrini, O.; Danielson, U. H.; Neyts, J.; Cecchetti, V. T. J. Med. Chem. 2013, 57,1952. pmid: 2999403
	(b) Chou, L. C.; Tsai, M. T.; Hsu, M. H.; Wang, S. H.; Way, T. D.; Huang, C. H.; Lin, H. Y.; Qian, K.; Dong, Y.; Lee, K. H.; Huang, L. J.; Kuo, S. C. J. Med. Chem. 2010, 53,8047. pmid: 2999403
	(c) Accurso, F.J.; Rowe, S.M.; Clancy, J.P.; Boyle, M.P.; Dunitz, J.M.; Durie, P.R.; Sagel, S.D.; Hornick, D.B.; Konstan, M.W.; Donaldson, S.H.; Moss, R.B.; Pilewski, J.M.; Rubenstein, R.C.; Uluer, A.Z.; Aitken, M.L.; Freedman, S.D.; Rose, L.M.; Mayer- Hamblett, N.; Dong, Q.M.; Zha, J.H.; Stone, A.J.; Olson, E.R.; Ordonez, C.L.; Campbell, P.W.; Ashlock, M.A.; Ramsey, B.W. N. Engl. J. Med. 2010, 363,1991. pmid: 2999403
	(d) Hazuda, D. J. Science 2000, 287,646. pmid: 2999403
	(e) Cairns, H.; Cox, D.; Gould, K. J.; Ingall, A. H.; Suschitzky, J. L. J. Med. Chem. 1985, 28,1832. doi: 10.1021/jm00150a014 pmid: 2999403
[35]	Jiang, S.F.; Xu, C.; Zhou, Z.W.; Zhang, Q.; Wen, X.H.; Jia, F.C.; Wu, A.X. Org. Lett. 2018, 20,4231. pmid: 29953242
[36]	Ma, Y.; Zhu, Y.; Zhang, D.; Meng, Y.; Tang, T.; Wang, K.; Ma, J.; Wang, J.; Sun, P. Green Chem. 2019, 21,478.
[37]	Li, W.; Liu, X.; Hao, X.; Cai, Y.; Lin, L.; Feng, X. Angew. Chem. Int. Ed. 2012, 51,8644.
[38]	(a) Zeng, R.; Dong, G. J. Am. Chem. Soc. 2015, 137,1408. doi: 10.1021/ja512306a pmid: 27699088
	(b) Zeng, R.; Chen, P.H.; Dong, G. ACS Catal. 2016, 6,969. doi: 10.1021/acscatal.5b02532 pmid: 27699088
[39]	Prakash, R.; Gogoi, S. Adv. Synth. Catal. 2016, 358,3046.
[40]	Shi, R.G.; Wang, X.H.; Liu, R.; Yan, C.G. Chem. Commun. 2016, 52,6280.
[41]	For selected papers, see: (a) Banerjee, A.; Santra, S. K.; Mohanta, P. R.; Patel, B. K. Org. Lett. 2015, 17,5678. doi: 10.1021/acs.orglett.5b02967 pmid: 32227905
	(b) McCauley, J.; Rudd, M.; Nguyen, K.; McIntyre, C.; Romano, J.; Bush, K.; Varga, S.; Ross, C.; Carroll, S.; DiMuzio, J.; Stahlhut, M.; Olsen, D.; Lyle, T.; Vacca, J.; Liverton, N. Angew. Chem. Int. Ed. 2008, 47,9104. pmid: 32227905
	(c) Felicetti, T.; Cannalire, R.; Pietrella, D.; Latacz, G.; Lubelska, A.; Manfroni, G.; Barreca, M.L.; Massari, S.; Tabarrini, O.; Kieć-Kononowicz, K.; Schindler, B.D.; Kaatz, G.W.; Cecchetti, V.; Sabatini, S. J. Med. Chem. 2018, 61,7827. pmid: 32227905
	(d) Dong, F.; Liu, J.Q.; Wang, X.S. Org. Lett. 2020, 22,2887. doi: 10.1021/acs.orglett.0c00497 pmid: 32227905
	(e) Qiu, Q.; Liu, B.; Cui, J.; Li, Z.; Deng, X.; Qiang, H.; Li, J.; Liao, C.; Zhang, B.; Shi, W.; Pan, M.; Huang, W.; Qian, H. J. Med. Chem. 2017, 60,3289. pmid: 32227905

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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