4,5-Dicyanopyridazine was found to react with pyrrole and indole counterparts not only as heterocyclic azadiene in inverse electron-demand Hetero Diels–Alder reactions, as previously evidenced, but even as a very reactive heterocyclic electrophile at C-4 carbon, in formal SNAr2 processes where a CN group acts as leaving group. In particular, operating in acetic acid as solvent, nucleophilic addition–elimination sequences allowed a facile access to pyrrolyl- and indolylpyridazines, through the corresponding 1,4-dihydropyridazine adducts.
Nucleophilic Aromatic Substitutions on 4,5-dicyanopyridazine. Pyrrole and Indole Systems as Carbon Nucleophiles / M. CECCHI; A. MICOLI; D. GIOMI. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:(2006), pp. 12281-12287. [10.1016/j.tet.2006.10.007]
Nucleophilic Aromatic Substitutions on 4,5-dicyanopyridazine. Pyrrole and Indole Systems as Carbon Nucleophiles
GIOMI, DONATELLA
2006
Abstract
4,5-Dicyanopyridazine was found to react with pyrrole and indole counterparts not only as heterocyclic azadiene in inverse electron-demand Hetero Diels–Alder reactions, as previously evidenced, but even as a very reactive heterocyclic electrophile at C-4 carbon, in formal SNAr2 processes where a CN group acts as leaving group. In particular, operating in acetic acid as solvent, nucleophilic addition–elimination sequences allowed a facile access to pyrrolyl- and indolylpyridazines, through the corresponding 1,4-dihydropyridazine adducts.File | Dimensione | Formato | |
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