Deprotonative magnesation and cadmation of [1,2,3]triazolo[1,5-a]pyridines - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2009

Deprotonative magnesation and cadmation of [1,2,3]triazolo[1,5-a]pyridines

Résumé

[1,2,3]Triazolo[1,5-a]pyridine and 3-substituted derivatives were regioselectively metalated at the 7 position using either Bu3MgLi or (TMP)3CdLi, the former at -10 °C and the latter at room temperature. The lithium arylmagnesates (R = H, Me, Ph) proved to react with iodine (34-75%) or 3,4,5- trimethoxybenzaldehyde (32-51%). Attempts to obtain the cross-couplings products using 2- bromopyridine under palladium catalysis failed, a result attributed to the low stability of these compounds. The corresponding lithium arylzincates reacted in 17 to 60% yield under the same reaction conditions. The lithium arylcadmates were either trapped with iodine (38-76%, R = H, Me, Ph, CN, 2- thienyl) or involved in palladium-catalyzed cross-coupling reactions with 2-bromopyridine (26-67%, R = H, Me, Ph). For R = 2-pyridyl, 3-(6-iodo-2-pyridyl)-[1,2,3]triazolo[1,5-a]pyridine was isolated in 73% yield. (TMP)3CdLi also proved suitable for the clean dideprotonation of two substrates (R = H, 2- thienyl), a result demonstrated by quenching with iodine (66-75%).

Domaines

Chimie organique
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Dates et versions

hal-00784559 , version 1 (05-02-2014)

Identifiants

Citer

Ghenia Bentabed-Ababsa, Fernando Blanco, Aicha Derdour, Florence Mongin, François Trécourt, et al.. Deprotonative magnesation and cadmation of [1,2,3]triazolo[1,5-a]pyridines. Journal of Organic Chemistry, 2009, 74 (1), pp.163-169. ⟨10.1021/jo801675h⟩. ⟨hal-00784559⟩
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