OXIDATIVE CYCLIZATION OF 5-ARYL-1-BENZYL-1,2,3-TRIAZOLES BEARING ELECTRON-RICH AROMATIC GROUPS: <i>ortho</i>/<i>ortho</i> AND <i>ortho</i>/<i>ipso</i> COUPLING

Authors

  • Maksim A. Boichenko Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119334
  • Konstantin V. Anisovich Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991
  • Mastaneh S. Shad Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 200F Gelestijnenlaan, Leuven 3001
  • Sergey S. Zhokhov Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991
  • Victor B. Rybakov Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991
  • Wim Dehaen Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 200F Gelestijnenlaan, Leuven 3001
  • Igor V. Trushkov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119334
  • Olga A. Ivanova Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119334

DOI:

https://doi.org/10.1007/6318

Keywords:

9H-dibenzo[c, e][1, 2, 3]triazolo[1, 5-a]azepines, 3, 3-disubstituted indoles, quinonoid compounds, 1, 3-triazoles, intramolecular oxidative aryl–aryl coupling, ipso attack

Abstract

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.

Author Biographies

Maksim A. Boichenko, Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119334

Department of Chemistry, post-graduate student

Konstantin V. Anisovich, Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991

Department of Chemistry, undergraduate student

Mastaneh S. Shad, Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 200F Gelestijnenlaan, Leuven 3001

Department of Chemistry, post-graduate student

Sergey S. Zhokhov, Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991

Department of Chemistry, scientific researcher

Victor B. Rybakov, Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991

Department of Chemistry, senior researcher

Wim Dehaen, Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 200F Gelestijnenlaan, Leuven 3001

Department of Chemistry, professor

Igor V. Trushkov, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119334

laboratory of directed functionalization of organic molecular systems, head of laboratory

Olga A. Ivanova, Department of Chemistry, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119334

Department of Chemistry, leading researcher

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Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers