Einhorn Reaction for the Synthesis of Aromatic Building Blocks for Macrocyclization

Abstract

The present study concerns the synthesis of bis(α-haloacetamidomethyl) and benzyldiamine sythons 1−3 (Scheme 1) through amidomethylation and their application for the preparation of benzoazamacroheterocycles. These synthons are useful as rigid building blocks containing the chromophoric NO_2 group. The methoxy function could be converted to the phenolic OH after ring closure, providing a proton-ionizable group in the macrocyclic cavity. We show three synthetic routes to prepare benzoazamacrocycles using synthons 1−3.

Additional details