Diversely functionalized oxacalix[2]arene[2]pyrimidines have been synthesized starting from a bis(methylsulfanyl)-substituted oxacalix[4]arene by two efficient post-macrocyclization pathways. Functionalized aryl groups were introduced on the pyrimidine building block via Liebeskind-Srogl cross-coupling reactions, while a variety of O-, S-, N-, and C-nucleophiles were inserted on the calixarene skeleton by nucleophilic aromatic substitution reactions on the bis(methylsulfonyl)oxacalix[4]arene analogue.

Oxacalix[2]arene[2]quinazoline macrocycles were prepared in good yields, as mixtures of syn and anti isomers, through nucleophilic aromatic substitution cyclocondensation reactions of 2,4-dichloroquinazolines and m-dihydroxybenzenes. The macrocyclization conditions were optimized and the isomeric ratio was investigated by means of one-step and frag-

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Efficient Post-Macrocyclization Functionalizations of Oxacalix[2]arene[2]pyrimidines. -Liebeskind-Srogl cross-coupling reaction of (I) with aryl boronic acids is utilized to prepare arylated calixarenes (III). The oxidation of (I) to the corresponding disulfone followed by substitution is optimized for a variety of O-, S-, N-and C-nucleophiles. -(VAN ROSSOM, W.; MAES, W.; KISHORE, L.; OVAERE, M.; VAN MEERVELT, L.; DEHAEN*, W.; Org. Lett. 10 (2008) 4, 585-588; Mol. Des. Synth., Kathol. Univ. Leuven, B-3001 Leuven, Belg.; Eng.) -R. Steudel 30-168

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