W. Maes, W. Dehaen
Sep 16, 2008
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Influential Citations
10
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Journal
ChemInform
Abstract
This account provides a summary of our research during the last 10 years (1997-2007) on the synthetic exploration of various macrostructures derived from dichloropyrimidine building blocks. Pyrimidine precursors have been used for the construction of functional porphyrinoids, (porphyrin) dendrimers, and heteracalix[n]arenes. meso-Pyrimidinyl-porphyrinoids have been synthesized starting from 4,6-dichloropyrimidine-5-carbaldehydes, and the resulting oligopyrrolic macrocycles were functionalized and superstructured in several different fashions. Pyrimidine-based (porphyrin) dendrimers have been constructed via a convergent strategy using a pyrimidine AB 2 -monomer. The dendritic surface was equipped with different moieties, allowing their exploration as dendritic oxidation catalysts. Finally, oxacalix[m]arene[m]pyrimidines (m = 2-6), a novel class ofheteracalix(heter)arenes, have recently been prepared via nucleophilic aromatic substitution reactions on 4,6-dihalopyrimidines. In these cyclooligomeric species, the pyrimidine component allows the introduction of a variety of functional moieties on the calixarene scaffold.