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Report | Regular issue | Vol 23, No. 3, 1985, pp.683-690
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0683
4-Nitro- and 4-Cyanopyridazines

Antonius T. M. Marcelis and Henk C. van der Plas*

*Laboratory of Organic Chemistry, Agricultural University, De Dreijen 5, 6703 BC Wageningen, The Netherlands


3-Acyl-1,2,4,5-tetrazines react with 1-nitro-2-dimethylaminoethene and 1-cyano-2-morpholinoethene by an inverse electron demand Diels-Alder reaction to give, after elimination of nitrogen and the secondary amine, the corresponding 3-aryl-5-nitro- and 3-aryl-5-cyanopyridazines. Besides these compounds, 1-benzylidene-2-dialkylaminomethylenehydrazines were isolated. They are also obtained from reaction of the 3-aryl-1,2,4,5-tetrazines with secondary aliphatic amines. Tetrazines with two electron-withdrawing groups like 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine, 3,6-bis(4-pyridyl)-1,2,4,5-tetrazine and 3,6-bis(piperidinocarbonyl)-1,2,4,5-tetrazine also react with the nitro- or cyanoenamine to give the corresponding 3,6-disubstituted 4-nitro- or 4-cyanopyridazines.