Dynamic combinatorial libraries of macrocycles derived from phthalic aldehydes and α,ω-diamines

Abstract

Dynamic combinatorial chemistry methodology was used to obtain eleven new polyazamacrocycles derived from isophthalic and terephthalic aldehyde and α,ω-diamines. Simple templates, such as alkali metal salts, were found to amplify large macrocycles: 45-membered [3+3]hexaazacrown and 60-membered [4+4]octaazacrown. Parent imine libraries were converted into corresponding secondary libraries of amines using a fast reduction protocol. Methyl carbamate protection of amine group allowed convenient isolation of polyazamacrocycles in very good yields.