Polish journal of chemistry vol:82 pages:1145-1160
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-Pyrimidinylporphyrinoids 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 AB2-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 of heteracalix(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.