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1 2008

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Macrostructures Derived from Dichloropyrimidines

Maes W., Dehaen W.

Polish Journal of Chemistry

2008

Vol. 82, nr 6

1146-1160

This account provides a summary of our research during the last 10 years (1997-2007) on the synthetic exploration of various macro structures derived from dichloropyrimidine building blocks. Pyrimidine precursors have been used for the construction of functional porphyrinoids, (porphyrin) dendrimers, and heteracalix[n]arenes. meso- Pyri midinyl - porphyrinoids have been synthesized starting from 4,6-dichloropyrimidine- 5-carbaldehydes, and the result ing oligopyrrolic macrocycles were functionalized and superstructured in several different fashions. Pyrimidine-based (porphyrin) dendrimers have been constructed via a convergent strategy using a pyrimidine AB2-monomer. The dendritic surface was equipped with different moieties, al lowing their exploration as dendritic oxidation catalysts. Finally, oxacalix[m]arene[m]pyrimidines (m = 2-6), a novel class of heteracalix(heter)arenes, have recently been prepared via nucleophilic aromatic substitution reactions on 4,6-dihalopyrimidines. In these cyclooligomeric species, the pyrimidine component al lows the introduction of avariety of functional moieties on the calixarene scaf fold.