Synthesis of polyazamacrocyclic compounds via modified Richman-Atkins cyclization of beta-trimethylsilylethanesulfonamides.

The Richman-Atkins cyclization remains one of the most widely used methods for the preparation of macrocyclic polyamines. The use of beta-trimethylsilylethanesulfonamides (SES-sulfonamides) for the preparation of polyazamacrocyclic compounds is described. This expands existing Richman-Atkins sulfonamide macrocyclization methodology, and it successfully enables preparation of labile polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes, not previously available in appreciable quantities.