Preparation of Pyrimidinophanes from Pyrimidine Bases.

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  • Itahara Toshio
    Institute of Chemistry, College of Liberal Arts, Kagoshima University

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  • Preparation of Pyrimidinophanes from Py

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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.

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