DESIGN AND SYNTHESIS OF A HETEROCYCLIC AMINE RECEPTOR

After a short review on the amine receptors already published in the l iterature, the design of a new host 1 is described. This new host poss esses two heterocyclic parts (isoquinoline and pyridine) separated by a flexible arm. The synthesis of receptor 1 involves regioselective ac ylation or halogenoacylation at the C-7 of isoquinoline followed by a Willgerodt-Kindler reaction affording the isoquinoline-7-acetic acid d erivatives 4b,c. Coupling of 4c with 2-aminopyridine gives the require d host 1. The association constants of this latter compound with some amine guests are determined using the classical NMR titration method. Copyright (C) 1996 Elsevier Science Ltd