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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

Maksim A. Boichenko, Konstantin V. Anisovich, Mastaneh S. Shad, Sergey S. Zhokhov, Victor B. Rybakov, Wim Dehaen, Igor V. Trushkov, Olga A. Ivanova
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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.


Keywords


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

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