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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
a   Xi’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
a   Xi’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∗
b   School of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, P. R. of China
,
Qiuyu Zhang∗
a   Xi’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
› Author AffiliationsThe authors are grateful for the support and funding from the National Natural Science Foundation of China (No. 21702165 and No. 51673156) and the Natural Science Foundation of Shaanxi Province (No. 2018JQ2018). Supported by the Fundamental Research Funds for the Central Universities (No. 3102017jc01001).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1364-9308.
  • Supporting Information


Publication History

Received: 29 December 2020

Accepted after revision: 19 January 2021

Accepted Manuscript online:
20 January 2021

Article published online:
24 February 2021

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  • References

    • 1a Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
      CrossrefPubMed
    • 1b Kerru N, Maddila S, Jonnalagadda SB. Curr. Org. Chem. 2019; 23: 3154
    • 1c Ju Y, Varma RS. J. Org. Chem. 2006; 71: 135
      CrossrefPubMed
    • 1d Zárate-Zárate D, Aguilar R, Hernández-Benitez RI, Labarrios EM, Delgado F, Tamariz J. Tetrahedron 2015; 71: 6961
      Crossref
    • 1e Leeson PD, Springthorpe B. Nat. Rev. Drug Discovery 2007; 6: 881
      CrossrefPubMed
    • 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
      Crossref
    • 2c Shipman M. Contemp. Org. Synth. 1995; 2: 1
      Crossref
    • 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
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 3c Yin H, Xu Y, Qian X. Bioorg. Med. Chem. 2007; 15: 1356
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 3e Yan M, Zhao J, Sun D, Sun W, Zhang B, Deng W, Zhang D, Wang L. Tetrahedron 2017; 73: 3355
      Crossref
    • 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
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 4c Sinha SH, Owens EA, Feng Y, Yang Y, Xie Y, Tu Y, Henary M, Zheng YG. Eur. J. Med. Chem. 2012; 54: 647
      CrossrefPubMed
    • 4d Lee H, Berezin MY, Henary M, Strekowski L, Achilefu S. J. Photochem. Photobiol., A 2008; 200: 438
      CrossrefPubMed
    • 5a Park KY, Song HJ, Heo JN. Adv. Synth. Catal. 2015; 357: 3197
      Crossref
    • 5b Shi R, Lu L, Xie H, Yan J, Xu T, Zhang H, Qi X, Lan Y, Lei A. Chem. Commun. 2016; 52: 13307
      CrossrefPubMed
    • 5c Wang Q, Zhang L, Yao J, Qiu G, Li X, Zhou H. J. Org. Chem. 2018; 83: 4092
      CrossrefPubMed
    • 5d Bi C, Zhang L, Qiu G, Li X, Yao J, Zhou H. Org. Biomol. Chem. 2018; 16: 3006
      CrossrefPubMed
  • 6 Majeed K, Wang L, Liu B, Guo Z, Zhou F, Zhang Q. J. Org. Chem. 2021; 86: 207
    CrossrefPubMed
    • 7a Zhu W, Ma D. Chem. Commun. 2004; 888
      PubMed
    • 7b Cai Q, Zhu W, Zhang H, Zhang Y, Ma D. Synthesis 2005; 496