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Oxidative cyclization of 5-aryl-1-benzyl-1,2,3-triazoles bearing electron-rich aromatic groups: ortho/ortho and ortho/ipso coupling

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Chemistry of Heterocyclic Compounds Aims and scope

The intramolecular oxidative coupling of electron-rich aromatic groups in 5-(het)aryl-1-(het)arylalkyl-1H-1,2,3-triazoles was studied in detail. Under treatment with phenyliodoso bis(trifluoroacetate) and boron trifluoride etherate these substrates afforded products of either ortho/ortho or ortho/ipso coupling depending on the nature of aromatic groups and reaction conditions applied. It was found that for substrates which are capable for both types of coupling, ortho-/ipso-adducts are formed under kinetic control while ortho-/ortho-products are formed under thermodynamic control. The developed procedures allow preparation of complex polycyclic azaheterocycles from simple precursors in two steps only.

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This work was supported by Russian Science Foundation (grant 18-13-00449).

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Authors and Affiliations

  1. Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Maksim А. Boichenko, Konstantin V. Anisovich, Sergey S. Zhokhov, Victor B. Rybakov & Olga А. Ivanova

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119334, Russia

    Maksim А. Boichenko, Igor V. Truhskov & Olga А. Ivanova

  3. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 200F Gelestijnenlaan, 3001, Leuven, Belgium

    Mastaneh S. Shad & Wim Dehaen

Authors
  1. Maksim А. Boichenko
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  2. Konstantin V. Anisovich
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  3. Mastaneh S. Shad
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  4. Sergey S. Zhokhov
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  5. Victor B. Rybakov
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  6. Wim Dehaen
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  7. Igor V. Truhskov
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  8. Olga А. Ivanova
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Corresponding authors

Correspondence to Igor V. Truhskov or Olga А. Ivanova.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 817–822

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Boichenko, M.А., Anisovich, K.V., Shad, M.S. et al. Oxidative cyclization of 5-aryl-1-benzyl-1,2,3-triazoles bearing electron-rich aromatic groups: ortho/ortho and ortho/ipso coupling. Chem Heterocycl Comp 57, 817–822 (2021). https://doi.org/10.1007/s10593-021-02985-5

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  • DOI: https://doi.org/10.1007/s10593-021-02985-5

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