10330-57-1Relevant academic research and scientific papers
Ortho-Directed Metalation of 3-Heterosubstituted 4-Methyl-6-phenylpyridazines
Sitamze, Jean-Marie,Mann, Andre,Wermuth, Camille-Georges
, p. 271 - 276 (2007/10/02)
Side-chain metalation of 4-methyl-6-phenylpyridazines (2-4) with lithium diisopropylamide or 2,2,6,6-tetramethylpiperidide and subsequent alkylation with various electrophiles have been investigated.Depending on the substituent attached at the 3-position (Cl, OMe or NHCOtBu), the prepatration of the alkylated pyridazines was more or less efficient.
Diazines VII. A new synthetic route to the pyridazine antidepressant, minaprine using directed ortho metalation and Suzuki cross coupling reactions
Turck, A.,Ple, N.,Mojovic, L.,Queguiner, G.
, p. 488 - 492 (2007/10/02)
A new synthetic route has been developed for minaprine.The synthesis is based upon two reactions recently studied on pyridazine: metalation and cross coupling with transition metals.Some different routes have been tested starting from 3,6-dichloropyridazine.The best results were obtained by coupling phenylboronic acid with 3-chloro-6-methoxypyridazine then by metalating 3-methoxy-6-phenylpyridazine and reacting the lithio derivatives with methyl iodide. 3-Methoxy-4-methyl-6-phenylpyridazine was obtained.After hydrolysis of the ether moiety, chlorination and substitution by the amine, minaprine was obtained with an overall yield of 36percent.Keywords - pyridazine / metalation / cross-coupling
