Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2016

Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells

William Erb
Yury Halauko
  • Fonction : Auteur
Oleg Ivashkevich
  • Fonction : Auteur
Vadim Matulis
  • Fonction : Auteur
Florence Mongin

Résumé

N-Arylation of pyrrole with 3-iodo-4-methoxypyridine was investigated by copper catalysis under different conditions. The best conditions, that proved to be protocol A (CuI, DMEDA or TMEDA, K 3 PO 4 , DMF at 110 C) and above all protocol B (Cu 2 O, Cs 2 CO 3 , DMSO at 110 C), were applied to the synthesis of various N-(methoxypyridyl) pyrroles, indoles and benzimidazoles. The behavior of the different iodinated methoxypyridines was rationalized by evaluating the partial positive charge on the carbon bearing iodine from the 1 H NMR chemical shift of the corresponding deiodinated substrates. The reaction was next connected with the deprotometalation-iodolysis step generating iodinated methoxypyridines: straight involvement of the crude iodo intermediates in pyrrole N-arylation afforded the expected N-(methoxypyridyl) pyrroles in good yields. Several synthesized N-(methoxypyridyl) azoles exerted low to moderate antiproliferative activity in A2058 melanoma cells.

Dates et versions

hal-03875302 , version 1 (12-12-2022)

Identifiants

Citer

Madani Hedidi, Julien Maillard, William Erb, Frédéric Lassagne, Yury Halauko, et al.. Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells. Tetrahedron, 2016, 72 (39), pp.6467 - 6476. ⟨10.1016/j.tet.2016.08.056⟩. ⟨hal-03875302⟩
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