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Recent Advances in the Synthesis of Benzoheterocyclic Compounds Involving Isatins

  • Fengcheng Jia ,
  • Na Luo ,
  • Cheng Xu ,
  • Anxin Wu
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  • 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
* Corresponding authors. E-mail: ;

Received date: 2020-07-12

  Revised date: 2020-10-01

  Online published: 2020-10-28

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)

Abstract

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.

Cite this article

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 . DOI: 10.6023/cjoc202007034

References

[1]
(a) Silva, J.; Garden, S.; Pinto, A. J. Braz. Chem. Soc. 2001, 12,273.
[1]
(b) Bergman, J.; Lindstr?m, J.O. Tetrahedron 1985, 41,2879.
[2]
(a) Raj, A.; Raghunathan, R.; Sridevikumaria, M.R.; Raman, N. Bioorg. Med. Chem. 2003, 11,407.
[2]
(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.
[2]
(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.
[2]
(d) Bal, T.; Anand, B.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2005, 15,4451.
[2]
(e) Aboul-Fadl, T.; Bin-Jubair, F.; Aboul-Wafa, O. Eur. J. Med. Chem. 2010, 45,4578.
[3]
(a) Marti, C.; Carreira, E.M. J. Am. Chem. Soc. 2005, 127,11505.
[3]
(b) Mitsunuma, H.; Shibasaki, M.; Kanai, M.; Matsunaga, S. Angew. Chem. Int. Ed. 2012, 51,5217.
[3]
(c) Hodges, T.R.; Benjamin, N.M.; Martin, S.F. Org. Lett. 2017, 19,2254.
[3]
(d) Wu, H.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132,14052.
[3]
(e) Hughes, C.C.; Fenical, W. J. Am. Chem. Soc. 2010, 132,2528.
[3]
(f) Sun, C.; Lin, X.; Weinreb, S.M. J. Org. Chem. 2006, 71,3159.
[4]
(a) Kumar, V.; Poonam; Prasad, A.K.; Parmar, V.S. Nat. Prod. Rep. 2003, 20,565.
[4]
(b) Bentley, K.W. Nat. Prod. Rep. 2006, 23,444.
[5]
(a) Liu, Y, H. Liaoning Med. 2002, (4),18. (in Chinese)
[5]
( 刘英华, 辽宁医药, 2002, (4),18.)
[5]
(b) Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J. A., R.P.; Dayam, R.; Neamati, N. J. Med. Chem. 2008, 51,3367.
[5]
(c) Mendes da Silva, J.F.; Walters, M.; Al-Damluji, S.; Ganellin, C.R. Bioorg. Med. Chem. 2008, 16,7254.
[6]
(a) Ma, Z.Z.; Hano, Y.; Nomura, T.; Chen, Y.J. Heterocycles 1997, 46,541.
[6]
(b) Michael, J.P. Nat. Prod. Rep. 2007, 24,223.
[6]
(c) Koepfli, J.B.; Mead, J.F.; Brockman, J. A. J. Am. Chem. Soc. 1947, 69,1837.
[6]
(d) Koepfli, J.B.; Mead, J.F.; Brockman, J. A. J. Am. Chem. Soc. 1949, 71,1048.
[6]
(e) Ablondi, F.; Gordon, S.; Morton, J.II, Williams, J.H. J. Org. Chem. 1952, 17,14.
[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.
[8]
(a) Yang, Z.; Huang, D.; Wen, L.; Wang, J.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2018, 38,1725. (in Chinese)
[8]
( 杨政, 黄丹凤, 文岚, 王娟娟, 王克虎, 胡雨来, 有机化学, 2018, 38,1725.)
[8]
(b) Yang, F.; Sun, J.; Gao, H.; Yan, C.G. RSC Adv. 2015, 5,32786.
[8]
(c) Singh, G.S.; Desta, Z.Y. Chem. Rev. 2012, 112,6104.
[8]
(d) Liu, Y.; Wang, H.; Wan, J. Asian J. Org. Chem. 2013, 2,374.
[8]
(e) Varun, V.; Sonam, S.; Kakkar, R. Med. Chem. Commun. 2019, 10,351.
[9]
Cheng, D.; Ling, F.; Zheng, C.; Ma, C. Org. Lett. 2016, 18,2435.
[10]
Yuan, W.K.; Cui, T.; Liu, W.; Wen, L.R.; Li, M. Org. Lett. 2018, 20,1513.
[11]
Ao, C.; Yang, X.; Jia, S.; Xu, X.; Yuan, Y.; Zhang, D.; Hu, W. J. Org. Chem. 2019, 84,15331.
[12]
Xu, T.; Chen, K.; Zhu, H.Y.; Hao, W.J.; Tu, S.J.; Jiang, B. Org. Lett. 2020, 22,2414.
[13]
Ramakumar, K.; Maji, T.; Partridge, J.J.; Tunge, J.A. Org. Lett. 2017, 19,4014.
[14]
(a) Zhu, S.; Chen, C.; Duan, K.; Sun, Y.M.; Li, S.S.; Liu, Q.; Xiao, J. J. Org. Chem. 2019, 84,8440.
[14]
(b) Li, S.S.; Zhu, S.; Chen, C.; Duan, K.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21,1058.
[14]
(c) Wang, S.; An, X.D.; Li, S.S.; Liu, X.; Liu, Q.; Xiao, J. Chem. Commun. 2018, 54,13833.
[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.
[17]
Jiang, S.; Li, K.; Yan, J.; Shi, K.; Zhao, C.; Yang, L.; Zhong, G. J. Org. Chem. 2017, 82,9779.
[18]
(a) Mei, G.J.; Bian, C.Y.; Li, G.H.; Xu, S.L.; Zheng, W.Q.; Shi, F. Org. Lett. 2017, 19,3219.
[18]
(b) Jiang, K.M.; Luesakul, U.; Zhao, S.Y.; An, K.; Muangsin, N.; Neamati, N.; Jin, Y.; Lin, J. ACS Omega 2017, 2,3123.
[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.
[21]
(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.
[22]
(b) Xu, H.; Zhou, B.; Zhou, P.; Zhou, J.; Shen, Y.; Yu, F.C.; Lu, L.L. Chem. Commun. 2016, 52,8002.
[23]
(a) Wang, H.; Li, L.; Lin, W.; Xu, P.; Huang, Z.; Shi, D. Org. Lett. 2012, 14,4598.
[23]
(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.
[24]
(a) Gao, Q.; Liu, Z.; Wang, Y.; Wu, X.; Zhang, J.; Wu, A. Adv. Synth. Catal. 2018, 360,1364.
[24]
(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.
[26]
(a) Mhaske, S.B.; Argade, N.P. Tetrahedron 2006, 62,9787.
[26]
(b) Lee, S.; Son, J.K.; Jeong, B.; Jeong, T.C.; Chang, H.; Lee, E.S.; Jahng, Y. Molecules 2008, 13,272.
[26]
(c) D'yakonov, A.L.; Telezhenetskaya, M.V. Chem. Nat. Compd. 1997, 33,221.
[26]
(d) Michael, J.P. Nat. Prod. Rep. 2008, 25,166.
[26]
(e) Fang, J.; Zhou, J. Org. Biomol. Chem. 2012, 10,2389.
[26]
(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.
[26]
(g) Liang, J.L.; Cha, H.C.; Jahng, Y. Molecules 2011, 16,4861.
[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.
[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.
[34]
(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.
[34]
(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.
[34]
(d) Hazuda, D. J. Science 2000, 287,646.
[34]
(e) Cairns, H.; Cox, D.; Gould, K. J.; Ingall, A. H.; Suschitzky, J. L. J. Med. Chem. 1985, 28,1832.
[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.
[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.
[38]
(b) Zeng, R.; Chen, P.H.; Dong, G. ACS Catal. 2016, 6,969.
[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.
[41]
(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.
[41]
(c) Felicetti, T.; Cannalire, R.; Pietrella, D.; Latacz, G.; Lubelska, A.; Manfroni, G.; Barreca, M.L.; Massari, S.; Tabarrini, O.; Kie?-Kononowicz, K.; Schindler, B.D.; Kaatz, G.W.; Cecchetti, V.; Sabatini, S. J. Med. Chem. 2018, 61,7827.
[41]
(d) Dong, F.; Liu, J.Q.; Wang, X.S. Org. Lett. 2020, 22,2887.
[41]
(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.
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