As previously reported with pyrrole and indole C-nucleophiles, 4,5-dicyanopyridazine (DCP) showed remarkable reactivity as a heterocyclic electrophile at the C-4 carbon toward amino nucleophiles. Aminocyanopyridazines, the formal SNAr2 products, have been easily synthesized in satisfactory yields through the facile substitution of a CN group of DCP, that behaves as leaving group. Operating in different solvents, the best results were generally obtained with a medium polar solvent, such as THF. The introduction of amino functionalities into the pyridazine system allows a desymmetrization of the starting material and opens the way to further synthetic elaborations.

Nucleophilic aromatic substitutions on 4,5-dicyanopyridazine. Part 2: Nitrogen nucleophiles / Renzo Alfini; Elisa Calamai; Antonella Salvini; Donatella Giomi. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 69:(2013), pp. 3475-3479. [10.1016/j.tet.2013.02.052]

Nucleophilic aromatic substitutions on 4,5-dicyanopyridazine. Part 2: Nitrogen nucleophiles

ALFINI, RENZO;SALVINI, ANTONELLA;GIOMI, DONATELLA
2013

Abstract

As previously reported with pyrrole and indole C-nucleophiles, 4,5-dicyanopyridazine (DCP) showed remarkable reactivity as a heterocyclic electrophile at the C-4 carbon toward amino nucleophiles. Aminocyanopyridazines, the formal SNAr2 products, have been easily synthesized in satisfactory yields through the facile substitution of a CN group of DCP, that behaves as leaving group. Operating in different solvents, the best results were generally obtained with a medium polar solvent, such as THF. The introduction of amino functionalities into the pyridazine system allows a desymmetrization of the starting material and opens the way to further synthetic elaborations.
2013
69
3475
3479
Renzo Alfini; Elisa Calamai; Antonella Salvini; Donatella Giomi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/822081
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