Synthesis of 1,4-disubstituted pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines by means of SNAr and palladium-catalysed reactions - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue European Journal of Inorganic Chemistry Année : 2015

Synthesis of 1,4-disubstituted pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines by means of SNAr and palladium-catalysed reactions

Résumé

The first efficient synthesis of various 1,4-disubstituted pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines is reported. The reactivity toward chlorine release at the C-1 and C-4 positions was investigated. SNAr and palladium-catalysed cross-coupling reactions were carried out, and conditions were optimised for each procedure. 1,4-Bis(het)aryl derivatives were obtained under a Suzuki cross-coupling procedure whereas SNAr substitution was achieved mainly at C-1 in preference to C-4. The monosubstituted C-4 morpholino derivative was used as a starting material to provide dissymmetrical 1,4-diaminated or 1-(het)aryl-4-morpholino products.

Domaines

Matériaux

Dates et versions

hal-01166893 , version 1 (23-06-2015)

Identifiants

Citer

Rabia Belaroussi, Ahmed El Hakmaoui, Nathalie Percina, Agnès Chartier, Mathieu Marchivie, et al.. Synthesis of 1,4-disubstituted pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines by means of SNAr and palladium-catalysed reactions. European Journal of Inorganic Chemistry, 2015, 18, pp.4006-4017. ⟨10.1002/ejoc.201500294⟩. ⟨hal-01166893⟩
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