19064-72-3Relevant articles and documents
Electrochemical reduction of 1,4-disubstituted phthalazines
Yanilkin,Buzykin,Morozov,Nastapova,Maksimyuk,Eliseenkova
, p. 1636 - 1646 (2001)
Electrochemical reduction in dimethylformamide of unsymmetrical 1-Cl-4-X-phthalazines and symmetrical 1,4-X2-phthalazines (X = Cl, PhO, MeO, EtO, i-PrO) was studied by voltammetry and electrolysis-ESR. The electron trasfer on 1,4-dichlorophthalazine and unsymmetrical 1-Cl-4-X-phthalazines induces anionoid elimination of Cl and X, pyridazine ring cleavage, and phthalonitrile formation. In this previously unknown process the transfer of two electrons induces cleavage of three σ bonds and formation of two new π bonds. The reduction of 1,4-dialkoxy(diaryloxy)phthalazines involves formation of stable radical anions which undergo no heteroring cleavage. Possible mechanisms of the processes studied were discussed. It was assumed that the same mechanism with pyridazine ring cleavage may be realized with other phthalazine derivatives and heteroannelated pyridazines containing readily leaving nucleofuge groups α to nitrogens.
Phase transfer catalyzed reductive acylation of nitrogen-containing heteroaromatics with acetylcobalt tetracarbonyl
Wang, Ming de,Alper, Howard
, p. 169 - 173 (2007/10/02)
Phase transfer catalyzed reductive ring-cleavage acylation of isoxazoles or isothiazoles with acetylcobalt tetracarbonyl gives N-acylated 1-amino-2-alkene-3-ones or thiones.Under the same conditions phthalazine, quinoline and isoquinoline react with acetylcobalt tetracarbonyl to give N-acylated dimers.The reactivity of several other nitrogen-containing heterocycles was also investigated.
