Nucleophilic aromatic substitutions on 4,5-dicyanopyridazine. Pyrrole and indole systems as carbon nucleophiles

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 S NAr2 processes where a CN...

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Bibliographic Details
Published in:Tetrahedron 2006-12, Vol.62 (52), p.12281-12287
Main Authors: Cecchi, Marco, Micoli, Alessandra, Giomi, Donatella
Format: Article
Language:English
Subjects:
1,4-Dihydropyridazine adducts
4,5-Dicyanopyridazine
Addition–elimination processes
Nucleophilic aromatic substitutions
Pyrrole and indole nucleophiles
Pyrrolylpyridazines and indolylpyridazines
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Summary: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 S NAr2 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.10.007