N-Iodosuccinimide (NIS) Promoted Synthesis of 3-Substituted Indole Derivatives

doi:10.6023/cjoc202202020

Abstract

A catalytic procedure for Michael addition reaction of indole or its derivatives with α,β-unsaturated ketones catalyzed by N-halosuccinimide has been successfully developed. Firstly, the Michael addition reaction of indole with chalcone was used as the template reaction, and the optimal conditions of the reaction were explored. The experimental results show that the optimal condition employs 10 mol% N-iodosuccinimide (NIS) as catalyst, CH₃CN as solvent, room temperature as reaction temperature and 18 h as reaction time. Under this optimized conditions, the reaction of chalcone and its derivatives with various α,β-unsaturated ketone can proceed smoothly to obtain the aimed product. The yields of these reactions ranged from 51% to 90%. The reaction conditions are mild and the reaction operation is simple.

Key words: N-iodosuccinimide (NIS), catalysis, indole, α,β-unsaturated ketone, Michael addition

Cite this article

Cunwei Qian, Rong Han, Zhixing Shen, Qian Li, Xuanrong Chen. N-Iodosuccinimide (NIS) Promoted Synthesis of 3-Substituted Indole Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2496-2503.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

References 31

[1]	(a) Shiri, M. Chem. Rev. 2012, 112, 3508. doi: 10.1021/cr2003954 pmid: 16836303
	(b) Yamashita, T.; Kawai, N.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2005, 127, 15038. pmid: 16836303
	(c) Baran, P. S.; Guerrero, C. A.; Hafensteiner, B. D.; Ambhaikar, N. B. Angew. Chem., Int. Ed. 2005, 44, 3892. doi: 10.1002/anie.200500655 pmid: 16836303
	(d) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644. doi: 10.1021/cr0683966 pmid: 16836303
	(e) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875. pmid: 16836303
	(f) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. doi: 10.1021/cr040639b pmid: 16836303
	(g) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079. doi: 10.1021/cr0201068 pmid: 16836303
	(h) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. doi: 10.1021/cr020033s pmid: 16836303
[2]	Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 25255204
[3]	Yu, R.; Fang, X. Chin. J. Org. Chem. 2021, 41, 2532. (in Chinese) doi: 10.6023/cjoc202100048
	(余融融, 方显杰, 有机化学, 2021, 41, 2532.) doi: 10.6023/cjoc202100048
[4]	Szmuszkovicz, J. J. Am. Chem. Soc. 1957, 79, 2819. doi: 10.1021/ja01568a041
[5]	Zhang, X.; Jones-Mensah, E.; Deobald, J.; Magolan, J. Adv. Synth. Catal. 2019, 361, 5548. doi: 10.1002/adsc.201901037
[6]	Harrington, P. E.; Kerr, M. A. Synlett 1996, 1047.
[7]	Yadav, J.; Abraham, S.; Reddy, B. S.; Sabitha, G. Synthesis 2001, 2001, 2165. doi: 10.1055/s-2001-18068
[8]	Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109. pmid: 12636368
[9]	Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 46, 2479. doi: 10.1016/j.tetlet.2005.02.044
[10]	Liang, D.; Li, X.; Zhang, W.; Li, Y.; Zhang, M.; Cheng, P. Tetrahedron Lett. 2016, 57, 1027. doi: 10.1016/j.tetlet.2016.01.078
[11]	Zhan, Z.-P.; Yang, R.-F.; Lang, K. J. T. L. Tetrahedron Lett. 2005, 46, 3859.
[12]	(a) Komoto, I.; Kobayashi, S. J. Org. Chem. 2004, 69, 680. doi: 10.1021/jo0353177
	(b) Azizi, N.; Arynasab, F.; Saidi, M. R. Org. Biomol. Chem. 2006, 4, 4275. doi: 10.1039/B610263H
	(c) Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. J. Mol. Catal. A 2006, 244, 168. doi: 10.1016/j.molcata.2005.09.005
	(d) Li, D.-P.; Guo, Y.-C.; Ding, Y.; Xiao, W.-J. Chem. Commun. 2006, 799.
	(e) Xu, L. W.; Zhou, W.; Yang, L.; Xia, C. G. Synth. Commun. 2007, 37, 3095. doi: 10.1080/00397910701544737
[13]	(a) Hassel, O.; Rømming, C. Q. Q. Rev. Chem. Soc. 1962, 16, 1.
	(b) Bent, H. A. Chem. Rev. 1968, 68, 587. doi: 10.1021/cr60255a003
	(c) Weiss, R.; Miess, G. E.; Haller, A.; Reinhardt, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 103.
	(d) Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686. doi: 10.1002/(SICI)1521-3773(19990917)38:18＜2686::AID-ANIE2686＞3.0.CO;2-6
[14]	Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry, University Science Books, Sausalito, CA, 2004, p. 162.
[15]	(a) Kilah, N. L.; Wise, M. D.; Serpell, C. J.; Thompson, A. L.; White, N. G.; Christensen, K. E.; Beer, P. D. J. Am. Chem. Soc. 2010, 132, 11893. doi: 10.1021/ja105263q
	(b) Jentzsch, A. V.; Emery, D.; Mareda, J.; Metrangolo, P.; Resnati, G.; Matile, S. Angew. Chem., Int. Ed. 2011, 50, 11675. doi: 10.1002/anie.201104966
	(c) Carlsson, A.-C. C.; Graefenstein, J.; Budnjo, A.; Laurila, J. L.; Bergquist, J.; Karim, A.; Kleinmaier, R.; Brath, U.; Erdelyi, M. J. Am. Chem. Soc. 2012, 134, 5706. doi: 10.1021/ja301341h
	(d) Raatikainen, K.; Rissanen, K. Chem. Sci. 2012, 3, 1235. doi: 10.1039/c2sc00997h
	(e) Cavallo, G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.; Terraneo, G. Chem. Rev. 2016, 116, 2478. doi: 10.1021/acs.chemrev.5b00484
[16]	(a) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217. pmid: 12188665
	(b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012. pmid: 12188665
	(c) Heinen, F.; Engelage, E.; Dreger, A.; Weiss, R.; Huber, S. M. Angew. Chem., Int. Ed. 2018, 57, 3830 doi: 10.1002/anie.201713012 pmid: 12188665
[17]	(a) Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114. doi: 10.1002/anie.200800128
	(b) Fourmigue, M. Curr. Opin. Solid State Mater. Sci. 2009, 13, 36. doi: 10.1016/j.cossms.2009.05.001
	(c) Legon, A. C. Phys. Chem. Chem. Phys. 2010, 12, 7736. doi: 10.1039/c002129f
	(d) Lu, Y.; Wang, Y.; Zhu, W. Phys. Chem. Chem. Phys. 2010, 12, 4543. doi: 10.1039/b926326h
[18]	(a) Walter, S. M.; Kniep, F.; Herdtweck, E.; Huber, S. M. Angew. Chem., Int. Ed. 2011, 50, 7187. doi: 10.1002/anie.201101672 pmid: 27465662
	(b) Bulfield, D.; Huber, S. M. Chem.-Eur. J. 2016, 22, 14434. doi: 10.1002/chem.201601844 pmid: 27465662
[19]	Gliese, J.-P.; Jungbauer, S. H.; Huber, S. M. Chem. Commun. 2017, 12052.
[20]	Takeda, Y.; Hisakuni, D.; Lin, C.-H.; Minakata, S. Org. Lett. 2015, 17, 318. doi: 10.1021/ol503426f
[21]	Kozak, J. A.; Wu, J.; Su, X.; Simeon, F.; Hatton, T. A.; Jamison, T. F. J. Am. Chem. Soc. 2013, 135, 18497. doi: 10.1021/ja4079094
[22]	Kiyani, H.; Kanaani, A.; Ajloo, D.; Ghorbani, F.; Vakili, M. Res. Chem. Intermed. 2015, 41, 7739. doi: 10.1007/s11164-014-1857-5
[23]	Ruan, H.; Zhang, J.; Sun, S.; Yang, Y.; Zhu, X.; Lv, C. Chin. J. Org. Chem. 2017, 37, 2139. (in Chinese) doi: 10.6023/cjoc201701003
	(阮鸿力, 张婧圆, 孙赛, 杨颖, 朱小磊, 吕成伟, 有机化学, 2017, 37, 2139.)
[24]	Xu, L.; Ye, Q.; Cheng, D.; Li, X.; Xu, X. Chin. J. Org. Chem. 2019, 39, 2645. (in Chinese)
	(许露露, 叶倩雯, 程冬萍, 李小年, 许孝良, 有机化学, 2019, 39, 2645.) doi: 10.6023/cjoc201812029
[25]	Li, S.-S.; Lin, H.; Zhang, X.-M.; Dong, L. Org. Biomol. Chem. 2015, 13, 1254. doi: 10.1039/C4OB02124J
[26]	Yoshida, Y.; Ishikawa, S.; Mino, T.; Sakamoto, M. Chem. Commun. 2021, 57, 2519. doi: 10.1039/D0CC07733J
[27]	Gao, Z.; Wang, Y.; Song, H.; Xu, Z.; Jia, Y. Chin. J. Org. Chem. 2021, 41, 3126. (in Chinese) doi: 10.6023/cjoc202102006
	(高中润, 王媛, 宋航, 徐正仁, 贾彦兴, 有机化学, 2021, 41, 3126.) doi: 10.6023/cjoc202102006
[28]	Li, Z. G.; Wang, Q. M.; Huang, J. M. Preparation of Organic Intermediates, 2nd ed., Chemical Industry Press, Beijing, 1996, p. 8. (in Chinese)
	(李在国, 汪清民, 黄君珉, 有机中间体制备, 第2版, 化学工业出版社, 北京, 1996, p. 8.)
[29]	Zhang, Y.; Zhu, C. Chin. J. Org. Chem. 2012, 32, 2283. (in Chinese) doi: 10.6023/cjoc201210030
	(张艳, 朱成建, 有机化学, 2012, 32, 2283.) doi: 10.6023/cjoc201210030
[30]	Maiti, G.; Kundu, P. Synth. Commun. 2007, 37, 2309. doi: 10.1080/00397910701410749
[31]	Liu, J.; Zhang, Y.; Yue, Y.; Wang, Z.; Shao, H.; Zhuo, K.; Lv, Q.; Zhang, Z. J. Org. Chem. 2019, 84, 12946. doi: 10.1021/acs.joc.9b01586

N-碘丁二酰亚胺(NIS)催化3-取代吲哚衍生物的合成