Synthesis of 1,2,3-Triazole-Fused Indole Derivatives via Copper-Catalyzed Cascade Reaction

Kashif Majeed; Bangjie Liu; Fengtao Zhou; Qiuyu Zhang

doi:10.1055/a-1364-9308

Synthesis, Table of Contents

Synthesis 2021; 53(12): 2103-2113
DOI: 10.1055/a-1364-9308

paper

Synthesis of 1,2,3-Triazole-Fused Indole Derivatives via Copper-Catalyzed Cascade Reaction

Kashif Majeed

^aXi’an Key Laboratory of Functional Organic Porous Materials, Department of Applied Chemistry, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. of China

,

Bangjie Liu

^aXi’an Key Laboratory of Functional Organic Porous Materials, Department of Applied Chemistry, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. of China

,

Fengtao Zhou∗

^bSchool of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, P. R. of China

,

Qiuyu Zhang∗

^aXi’an Key Laboratory of Functional Organic Porous Materials, Department of Applied Chemistry, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. of China

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Abstract

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Abstract

A copper-catalyzed tandem reaction has been developed for the synthesis of 1,2,3-triazole-fused indole derivatives. This protocol allowed us to access a wide range of 1,2,3-triazole-fused indole derivatives in moderate to excellent yields. The 1,2,3-triazole-fused indole derivatives emit blue and greenish light when excited at 365 nm. The products were further explored for their quantum efficiency and photophysical properties.

Key words

1,2,3-triazole-fused indoles - [3+2] cycloaddition - C–N bond formation - tandem reaction - sodium azide

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References

References

1a Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
1b Kerru N, Maddila S, Jonnalagadda SB. Curr. Org. Chem. 2019; 23: 3154
1c Ju Y, Varma RS. J. Org. Chem. 2006; 71: 135
1d Zárate-Zárate D, Aguilar R, Hernández-Benitez RI, Labarrios EM, Delgado F, Tamariz J. Tetrahedron 2015; 71: 6961
1e Leeson PD, Springthorpe B. Nat. Rev. Drug Discovery 2007; 6: 881

2a Kozikowski AP. In Comprehensive Heterocyclic Chemistry, Vol. 1; Katritzky A. R., Rees C. W. Pergamon Press; Oxford: 1984: 413
2b Lipshutz BH. Chem. Rev. 1986; 86: 795
2c Shipman M. Contemp. Org. Synth. 1995; 2: 1

3a Varney MD, Marzoni GP, Palmer CL, Deal JG, Webber S, Welsh KM, Bacquet RJ, Bartlett CA, Morse CA. J. Med. Chem. 1992; 35: 663
3b López-Rodríguez ML, Porras E, Morcillo MJ, Benhamú B, Soto LJ, Lavandera JL, Ramos JA, Olivella M, Campillo M, Pardo L. J. Med. Chem. 2003; 46: 5638
3c Yin H, Xu Y, Qian X. Bioorg. Med. Chem. 2007; 15: 1356
3d Xue X, Zhang Y, Liu Z, Song M, Xing Y, Xiang Q, Wang Z, Tu Z, Zhou Y, Ding K, Xu Y. J. Med. Chem. 2016; 59: 1565
3e Yan M, Zhao J, Sun D, Sun W, Zhang B, Deng W, Zhang D, Wang L. Tetrahedron 2017; 73: 3355

4a Appelt K, Bacquet RJ, Bartlett CA, Booth CL. J, Freer ST, Fuhry MA. M, Gehring MR, Herrmann SM, Howland EF. J. Med. Chem. 1991; 34: 1925
4b Kamal A, Ramakrishna G, Nayak VL, Raju P, Rao AV. S, Viswanath A, Vishnuvardhan MV. P. S, Ramakrishna S, Srinivas G. Bioorg. Med. Chem. 2012; 20: 789
4c Sinha SH, Owens EA, Feng Y, Yang Y, Xie Y, Tu Y, Henary M, Zheng YG. Eur. J. Med. Chem. 2012; 54: 647
4d Lee H, Berezin MY, Henary M, Strekowski L, Achilefu S. J. Photochem. Photobiol., A 2008; 200: 438

5a Park KY, Song HJ, Heo JN. Adv. Synth. Catal. 2015; 357: 3197
5b Shi R, Lu L, Xie H, Yan J, Xu T, Zhang H, Qi X, Lan Y, Lei A. Chem. Commun. 2016; 52: 13307
5c Wang Q, Zhang L, Yao J, Qiu G, Li X, Zhou H. J. Org. Chem. 2018; 83: 4092
5d Bi C, Zhang L, Qiu G, Li X, Yao J, Zhou H. Org. Biomol. Chem. 2018; 16: 3006

6 Majeed K, Wang L, Liu B, Guo Z, Zhou F, Zhang Q. J. Org. Chem. 2021; 86: 207

7a Zhu W, Ma D. Chem. Commun. 2004; 888
7b Cai Q, Zhu W, Zhang H, Zhang Y, Ma D. Synthesis 2005; 496

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