Metal Template Reactions. XXV. N-Acyl Isatin Precursors for the Synthesis of Malonamido Macrocyclic Metal Complexes

Abstract

Reaction of sodium isatide with dimethylmalonyl dichloride yielded the oxazinoindole (6) rather than the expected product (4). The glyoxylamide (8), which served as a precursor to the macrocyclic complex (15), was therefore prepared by a sequence involving compounds (9), (10) and (7). Such a route makes use of the reactivity of N-acyl isatins and the protecting capacity of the benzyloxycarbonyl group. The structure of compound (6) was established by X-ray crystallography.