Synthesis of (thia)calix[4]arene oligomers: towards calixarene-based dendrimers

Thiacalix[4]arenes bearing two or four carboxylic functions on the lower rim served as starting compounds for the synthesis of novel calixarene oligomers connected by amidic functions. The cone conformers react smoothly with four molecules of 5-amino-calix[4]arene to yield the corresponding pentakis-calixarenes. On the other hand, because steric hindrance, the 1,3-alternate condenses only with two molecules leading thus to tris-calixarene, possessing a novel type of inherent chirality based on the 25,26-substitution pattern. The title compounds, which connect together ‘classical’ calixarene and thiacalixarene building blocks, represent a first step towards calixarene-based dendritic structures.