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

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

Publication History

Received: 29 December 2020

Accepted after revision: 19 January 2021

Accepted Manuscript online:
20 January 2021

Article published online:
24 February 2021

• 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