Pyridazines have been allowed to react with tetracyanoethylene oxide to give pyridazinium N-dicyanomethylides, which are subjected to vicarious nucleophilic substitution to afford the corresponding 4-substituted derivatives in moderate to good yields. The dicyanomethylene group is readily eliminated by a radical reaction, and 4-substituted pyridazines are obtained.
T. Itoh, Y. Matsuya, K. Nagata, M. Miyazaki, N. Tsutsumi and A. Ohsawa, J. Chem. Soc., Perkin Trans. 1, 1998, 1637 DOI: 10.1039/A800733K
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