Synthesis of Aza Macrocycles by Nucleophilic Ring Closure with Cesium Tosylamides

Article abstract of DOI:10.1021/jo00175a022

Long-chain diamines as their bis tosylamide derivatives are deprotonated by Cs2CO3 in dimethylformamide solution to give the dicesium salts.These react smoothly with various dibromides or dimesylates to afford the cyclic diamines as their tosyl derivatives.The yields, depending on the size of the ring, range between 25percent and 95percent of isolated product.The largest ring made, 1,12-diazaoctacosane (as the tosylamide derivative) was isolated in 60percent yield.The tosyl groups are readily removed with sodium amalgam in Na2HPO4-buffered methanolic solution.Chiral macrocyclic amines have also been prepared by using this cesium salt method.