Macrocyclic and macropolycyclic compounds based upon 1,3-disubstituted propane units

Abstract

Synthetic routes to the macrocyclic polyamine derivatives (1) and (3) are described, together with an investigation of the complexing properties of the triamines (1d) and (3d) with primary alkylammonium cations. Macrotricyclic and macrotetracyclic compounds may be obtained from the macrocycle (1) by a stepwise procedure whereas macrocycle (3b) can be converted into a macrotricyclic derivative in a one step alkylation procedure. The alkylation of the tetrahydropyrimidone (18) with αα′-dibromo-m-xylene gives the calix[4] arene analogue (19) which adopts the ‘cone’(21a) and ‘1,3-alternate’(21b) conformations. The macrocyclic hexa-amine (23) may be synthesized by a simple alkylation procedure whereas the octa-amine (27) required a systematic stepwise synthesis. The hexa-amine salt (23)·6 HBr shows selectivity in forming inclusion complexes with the dicarboxylate anions ^–O₂C(CH₂)_nCO₂^–.