Progress in Annulative Transformations from Indoles to Carbazoles: State of the Art

doi:10.6023/cjoc202007014

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 521-528.DOI: 10.6023/cjoc202007014 Previous Articles Next Articles

Review

吲哚多样化环化合成咔唑衍生物研究进展

杜玉英^a, 肖业元^b, 田福利^c, 韩利民^a^,^*(), 顾彦龙^b^,^*(), 竺宁^a

a 内蒙古工业大学化工学院呼和浩特 010051
b 华中科技大学化学与化工学院武汉 430074
c 海南科技职业大学海口 571126

收稿日期:2020-07-05 修回日期:2020-08-13 发布日期:2020-09-30
通讯作者: 韩利民, 顾彦龙
作者简介:
* Corresponding authors. E-mail: hanlimin@imut.edu.cn; klgyl@hust.edu.cn
基金资助:
内蒙古草原英才基金(841060); 国家自然科学基金(2171101076); 国家自然科学基金(21872060)

Progress in Annulative Transformations from Indoles to Carbazoles: State of the Art

Yuying Du^a, Yeyuan Xiao^b, Fuli Tian^c, Limin Han^a^,^*(), Yanlong Gu^b^,^*(), Ning Zhu^a

a Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051
b School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074
c Hainan Vocational University of Science and Technology, Haikou 571126

Received:2020-07-05 Revised:2020-08-13 Published:2020-09-30
Contact: Limin Han, Yanlong Gu
Supported by:
the Research Funds of Caoyuanyingcai Program of Inner Mongolia(841060); the National Natural Science Foundation of China(2171101076); the National Natural Science Foundation of China(21872060)

Carbazole is an important type of nitrogen organic compound containing aromatic heterocyclic ring. Carbazole derivatives are endowed with unique physical and chemical properties, and applied to natural products, various pharmacological activities, many drugs and photophysical materials. The concise and versatile synthetic strategies of ubiquity of carbazole analogues have attracted significant attention from the synthetic chemists. Herein, the current progress of annulation transformations from indoles to carbazole derivatives is summarized in recent 5 years. The representative samples of the cyclization strategies have been selected and divided into three types, respectively: [2+2'+2'] cyclization reaction, [2+2'+2"] cyclization reaction and [4+2] cycloaddition. The basic properties, advantages and limitations of each reaction are discussed in detail. A perspective is also given in this review.

Key words: carbazole derivatives, indoles, cyclization reaction, synthesis

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Yuying Du, Yeyuan Xiao, Fuli Tian, Limin Han, Yanlong Gu, Ning Zhu. Progress in Annulative Transformations from Indoles to Carbazoles: State of the Art[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 521-528.

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Fig. & Tab. 4

Scheme 1. MnBr(CO)5 catalyzed C—H functionalization of indoles with alkynes

Scheme 2. Cu(II) catalyzed the synthesis of hydroxyl substituted carbazoles

Scheme 3. Cyclization reaction of 2,3-allenols with indoles

Scheme 4. Synthesis of carbazoles via reactions of 2,3-unsub- stituted indole and acrylate or acrylonitrile

References 45

[1]	Akue-Gedu R.; Nauton L.; Thery V.; Bain J.; Cohen P.; Anizon F.; Moreau P. Bioorg. Med. Chem. 2010, 18, 6865. doi: 10.1016/j.bmc.2010.07.036
[2]	Goodwin S.; Smith A.F.; Horning E.C. J. Am. Chem. Soc. 1959, 81, 1903. doi: 10.1021/ja01517a031
[3]	Hirata K.; Ito C.; Furukawa H.; Itoigawa M.; Cosentino L.M.; Lee K.H. Bioorg. Med. Chem. Lett. 1999, 9, 119. pmid: 10021911
[4]	Issa S.; Walchshofer N.; Kassab I.; Termoss H.; Chamat S.; Geahchan A.; Bouaziz Z. Eur. J. Med. Chem. 2010, 45, 2567. doi: 10.1016/j.ejmech.2010.02.045
[5]	Al-Trawneh S.A.; Zahra J.A.; Kamal M.R.; El-Abadelah M.M.; Zani F.; Incerti M.; Cavazzoni A.; Alfieri R.R.; Petronini P.G.; Vicini P. Bioorg. Med. Chem. 2010, 18, 5873. doi: 10.1016/j.bmc.2010.06.098
[6]	Gallogly M.M.; Lazarus H.M.; Cooper B.W. Ther. Adv. Hematol. 2017, 8, 245. doi: 10.1177/2040620717721459 pmid: 29051803
[7]	Kosaraju W.J.; Zhou W.; Tam K.Y. ACS Chem. Neurosci. 2017, 8, 676. doi: 10.1021/acschemneuro.6b00388
[8]	Bao Y.; Liu B.; Wang H.; Du F.; Bai R. Anal. Methods. 2011, 3, 1274. doi: 10.1039/c1ay05194f
[9]	Shang X.F.; Li X.J.; Han J.; Jia S.Y.; Zhang J.L.; Xu X.F. Inorg. Chem. Commun. 2012, 16, 37. doi: 10.1016/j.inoche.2011.11.025
[10]	Mahapatra A.K.; Roy J.; Sahoo P. Bioorg. Med. Chem. Lett. 2012, 22, 5379. doi: 10.1016/j.bmcl.2012.07.055
[11]	Sinha S.; Kumar S.; Koner R.R.; Mathew J.; Nandi C.K.; Ghosh S. RSC Adv. 2013, 3, 6271. doi: 10.1039/c3ra23442h
[12]	Dong J.; Liu Y.; Hu J.; Baigude H.; Zhang H. Sens. Actuators, B 2018, 255, 952. doi: 10.1016/j.snb.2017.08.134
[13]	Du Y.-Y.; Han L.M.; Guo L.W.; She Z.C.; Cui J.; Lv L.; Gao R.X. Heterocycles 2020, 100, 633. doi: 10.3987/COM-20-14213
[14]	Lee C.W,; Lee J.Y. Dyes Pigm. 2014, 109, 1. doi: 10.1016/j.dyepig.2014.04.037
[15]	Han L.; Zu X.Y.; Cui Y.H.; Wu H.B.; Ye Q.; Gao J.R. Org. Electron. 2014, 15, 1536. doi: 10.1016/j.orgel.2014.04.016
[16]	Pansay S.; Prachumrak N.; Jungsuttiwong S. Tetrahedron Lett. 2012, 53, 4568. doi: 10.1016/j.tetlet.2012.06.067
[17]	Velasco D.; Jankauskas V.; Stumbraite J.; Grazulevicius J.V.; Getautis V. Synth. Met. 2009, 159, 654. doi: 10.1016/j.synthmet.2008.12.011
[18]	Ouyang X.H.; Zeng H.P.; Ding G.Y.; Jiang W.L.; Li J. Synth. Met. 2009, 159, 2063. doi: 10.1016/j.synthmet.2009.07.026
[19]	Kim H.M.; Choi J.M.; Lee J.Y. Org. Electron. 2017, 43, 130. doi: 10.1016/j.orgel.2017.01.021
[20]	Zhang K.; Xu H.J.; Liu Z.B.; Song C.J. Chin. J. Org. Chem. 2019, 39, 1142. (in Chinese) doi: 10.6023/cjoc201812005 pmid: 200E0BF8-840E-4498-A6EE-A77BC026B001
	张坤, 徐红进, 刘咨博, 宋传君, 有机化学, 2019, 39, 1142.). doi: 10.6023/cjoc201812005 pmid: 200E0BF8-840E-4498-A6EE-A77BC026B001
[21]	Li X.; Song Z.R.; Chen X.; Cai Y.C.; Liu Y.J.; Chen C.X.; Peng J.S. Chin. J. Org. Chem. 2020, 40, 950. (in Chinese) doi: 10.6023/cjoc201909040 pmid: 70897f9a-bfaa-4f5e-862e-43f012896ac4
	李雪, 宋子锐, 陈鑫, 蔡轶超, 刘雅婕, 陈春霞, 彭进松, 有机化学, 2020, 40, 950.). doi: 10.6023/cjoc201909040 pmid: 70897f9a-bfaa-4f5e-862e-43f012896ac4
[22]	Yamashita M.; Horiguchi H.; Hirano K.; Satoh T.; Miura M. J. Org. Chem. 2009, 74, 7481. doi: 10.1021/jo9016698
[23]	Guo T.L.; Jiang Q.B.; Huang F.; Chen J.P.; Yu Z.K. Org. chem. Front. 2014, 1, 707. doi: 10.1039/C4QO00122B
[24]	Jia J.L.; Shi J.J.; Zhou J.; Liu X.L.; Song Y.L.; Xu H.E.; Yi W. Chem. Commun. 2015, 51, 2925. doi: 10.1039/C4CC09823D
[25]	Shi L.J.; Zhong X.; She H.D.; Lei Z.Q.; Li F.W. Chem. Commun. 2015, 51, 7136. doi: 10.1039/C5CC00249D
[26]	Verma A.K.; Danodia A.K.; Saunthwal R.K.; Patel M.; Choudhary D. Org. Lett. 2015, 17, 3658. doi: 10.1021/acs.orglett.5b01476
[27]	Laha J.K.; Dayal N. Org. Lett. 2015, 17, 4742. doi: 10.1021/acs.orglett.5b02265
[28]	Zhou Q.L.; Zhu C.L.; Wu G.; Zhang Y.F.; Zhang M.; Su W.P. Chin. J. Org. Chem. 2017, 37, 2655. (in Chinese) pmid: 1F430D42-F612-46C4-BCDB-DD1FE57E43F4
	周全龙, 朱昌垒, 吴戈, 张远飞, 张敏, 苏伟平, 有机化学, 2017, 37, 2655.). doi: 10.6023/cjoc201705014 pmid: 1F430D42-F612-46C4-BCDB-DD1FE57E43F4
[29]	Qiao Y.; Wu X.-X.; Zhao Y.P.; Sun Y.Q.; Li B.G.; Chen S.F. Adv. Synth. Catal. 2018, 360, 2138. doi: 10.1002/adsc.v360.11
[30]	Chen S.P.; Li Y.X.; Ni P.H.; Huang H.W.; Deng G.J. Org. Lett. 2016, 18, 5384. doi: 10.1021/acs.orglett.6b02762
[31]	Chen S.P.; Wang L.R.; Zhang J.; Hao Z.R.; Huang. H. W.; Deng, G.J.J. Org. Chem. 2017, 82, 11182. doi: 10.1021/acs.joc.7b02305
[32]	Chen S.P.; Li Y.X.; Ni P.H.; Yang B.C.; Huang. H. W.; Deng, G.J.J. Org. Chem. 2017, 82, 2935. doi: 10.1021/acs.joc.6b02892
[33]	Gu Y.L.; Huang W.B.; Chen S.M.; Wang X. Org. Lett. 2018, 20, 4285. doi: 10.1021/acs.orglett.8b01707
[34]	Yiliqi. M. S. Thesis, Huazhong University of Science and Technology, Wuhan, 2019. (in Chinese)
	伊利琦, 硕士论文, 华中科技大学, 武汉, 2019.).
[35]	Paria S.; Reiser O. Adv. Synth. Catal. 2014, 557.
[36]	Matsuda Y.; Naoe S.; Oishi S.; Fujii N.; Ohno H. Chem.- Eur. J. 2015, 21, 1463. doi: 10.1002/chem.201405903
[37]	Guo B.J.; Huang X.; Fu C.L.; Ma S. M.Chem.- Eur. J. 2016, 22, 18343. doi: 10.1002/chem.v22.51
[38]	Saunthwal R.K.; Saini K.M.; Patel M.; Verma A.K. Tetrahedron 2017, 73, 2415. doi: 10.1016/j.tet.2017.03.028
[39]	Zhou C.J.; Gao H.; Huang S.L.; Zhang S.-S.; Wu J.Q.; Li B.; Jiang X.-X.; Wang H.G. ACS Catal. 2019, 9, 556. doi: 10.1021/acscatal.8b03595
[40]	Suarez A.; Garciagarcia P.; Fernandezrodriguez M.A.; Sanz R. Adv. Synth. Catal. 2014, 374.
[41]	Zheng X.J.; Lv L.Y.; Lu S.L.; Wang W. X.; Li Z. P.Org. Lett. 2014, 16, 5156. doi: 10.1021/ol5025053
[42]	Zhao J.-J.; Li P.; Xia C.G.; Li F.W. Chem.- Eur. J. 2015, 21, 16383. doi: 10.1002/chem.v21.46
[43]	Liu C.H.; Huang W.B.; Wang M.; Pan B.; Gu Y.L. Adv. Synth. Catal. 2016, 358, 2260. doi: 10.1002/adsc.v358.14
[44]	Stepherson J.R.; Ayala C.E.; Tugwell T.H.; Henry J.L.; Fronczek F.R.; Kartika R. Org. Lett. 2016, 18, 3002. doi: 10.1021/acs.orglett.6b01376
[45]	Du Y.-Y.; Xue W.Y.; Gao R.X.; Gu Y.L.; Han L.M. Tetrahedron. Lett. 2018, 59, 4221. doi: 10.1016/j.tetlet.2018.10.029

吲哚多样化环化合成咔唑衍生物研究进展

Progress in Annulative Transformations from Indoles to Carbazoles: State of the Art

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