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

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

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2021, Volume: 57, Number: 7-8, Pages: 817-822 Pages count : 6 DOI: 10.1007/s10593-021-02985-5

Authors

Boichenko Maksim А. ^1,2 , Anisovich Konstantin V. ¹ , Shad Mastaneh S. ³ , Zhokhov Sergey S. ¹ , Rybakov Victor B. ¹ , Dehaen Wim ³ , Truhskov Igor V. ² , Ivanova Olga А. ^1,2

Affiliations

1	Department of Chemistry, Lomonosov Moscow State University, Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
3	Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven, Belgium

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.

Boichenko M.А. , Anisovich K.V. , Shad M.S. , Zhokhov S.S. , Rybakov V.B. , Dehaen W. , Truhskov I.V. , Ivanova O.А.
Oxidative cyclization of 5-aryl-1-benzyl-1,2,3-triazoles bearing electron-rich aromatic groups: ortho/ortho and ortho/ipso coupling
Chemistry of Heterocyclic Compounds. 2021. V.57. N7-8. P.817-822. DOI: 10.1007/s10593-021-02985-5 WOS Scopus OpenAlex

Web of science:	WOS:000693553900003
Scopus:	2-s2.0-85115920305
OpenAlex:	W3198322475

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