A new class of calixarene-based macrocycles consisting of three to eight calixarene subunits has been prepared from starting 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropoxycalixare ne. The macrocyclization has been achieved by direct alkylation with 1,6-dibromohexane in DMF in the presence of NaH or via appropriate intermediates. Thus, the starting compound was transformed into bis-calixarenes bearing two bromoalkyl substituents or two hydroxyl groups in positions suitable for further cyclization. By the mutual reactions of the above noticed compounds supermacrocycles containing 3, 4, 6, and 8 calixarene subunits connected by hexamethylene chains have been prepared and characterized. This is a novel strategy to design a 'macrocycle of macrocycles'.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry