SELECTIVE DERIVATISATIONS OF RESORCARENES .2. MULTIPLE REGIOSELECTIVERING-CLOSURE REACTIONS

The condensation of the C-pentyl resorcarene 1 with long chain aliphat ic diamines 3a-d and excess formaldehyde leads under high dilution con ditions to tetrabenzoxazine derivatives 4a-d in which pairs of adjacen t oxazine rings are connected by an aliphatic chain. Six new rings are formed per resorcarene molecule during this reaction in a regioselect ive way. For one example (4a) the chiral cleft-like structure with C-2 symmetry was proved by single crystal X-ray analysis. Hydrolysis of t he oxazine rings gives the secondary amine derivatives 5a,b with C-2V symmetry in high yield. (C) 1997 Elsevier Science Ltd.