BELAROUSSI, Rabia; EL HAKMAOUI, Ahmed; PERCINA, Nathalie; CHARTIER, Agnès; MARCHIVIE, Mathieu; MASSIP, Stéphane; JARRY, Christian; AKSSIRA, Mohamed; GUILLAUMET, Gérald; ROUTIER, Sylvain

doi:10.1002/ejoc.201500294

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BELAROUSSI, Rabia
Institut de Chimie Organique et Analytique [ICOA]
Laboratoire de Chimie, Bioorganique et analytique

EL HAKMAOUI, Ahmed

PERCINA, Nathalie
Institut de Chimie Organique et Analytique [ICOA]

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European Journal of Inorganic Chemistry. 2015 n° 18, p. 4006-4017

Wiley-VCH Verlag

Résumé en anglais

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.< Réduire

Mots clés en anglais

Nitrogen heterocycles

Cross-coupling

Aromatic nucleophilic substitution

Palladium

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

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