Heterocyclic analogs of pleiadiene. XVI. Nitration of perimidine and its 1- and 2-methyl derivatives

Perimidine and 2-methylperimidine are nitrated by 1 mole of nitric acid in acetic acid to give a mixture of 4(9)- and 6(7)-mononitro derivatives. Renitration gives a mixture of 6,9- and 6,7-dinitroperimidines. Depending on the conditions, 6,7,9-trinitroperimidines and 4,6,7,9-tetranitroperimidines are formed when a large excess of nitric acid is present. 1-Methylperimidine is nitrated by 1 mole of nitric acid to give a mixture of 4-, 6-, and 7-mononitro derivatives.