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

• Published in: Tetrahedron Vol. 69; no. 16; pp. 3475 - 3479
• Main Authors: Alfini, Renzo, Calamai, Elisa, Salvini, Antonella, Giomi, Donatella
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.04.2013; Elsevier
• Subjects: Aminopyridazines; carbon; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; Cyano heterocycles; Cyanopyridazines; nitrogen; Nitrogen nucleophiles; Nucleophilic aromatic substitutions; organic compounds; Physical Sciences; Pyridazines; Science & Technology; solvents; Pyridazines; Nitrogen nucleophiles; Cyanopyridazines; Cyano heterocycles; Nucleophilic aromatic substitutions; Aminopyridazines; PYRROLE; INDOLE SYSTEMS; DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2013.02.052

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. [Display omitted]