Treatment of pyrimidine bases such as uracil, thymine, and 5-fluorouracil with X(CH2)nX (X = I or Br; n = 4—12) gave three types of pyrimidinophanes. When the numbers of carbon atoms of X(CH2)nX are odd numbers (n = 5, 7, 9, 11), three structures of pyrimidinophanes could be differentiated on the basis of the 13C NMR and mass spectra. Treatment of pyrimidinophanes with 1,4-naphthoquinone or maleimides in the presence of palladium(II) acetate gave the coupling products. Reaction of pyrimidinophanes with NaNO2 in the presence of palladium(II) acetate led to the nitration.
Bulletin of the Chemical Society of Japan 69 (11), 3239-3246, 1996
The Chemical Society of Japan