Synthesis of New N-Pivot Lariat Crown Ethers Containing a Propylene Linkage in the Side Arm

A series of new 15- and 18-membered N-pivot lariat aza-crown ethers having a propylene linkage in the side arm was prepared starting from functionalized diethanolamines and functionalized lariat aza-crown ethers containing the easily modified benzotriazole moiety. Addition reactions of such derivatives to electron-rich vinyl ethers or vinylamides followed by displacement of the benzotriazolyl group in the addition products by hydrogen (by reduction with LiAlH(4)) gives a variety of N-(3-oxo-3-substituted)- and N-(3-aza-3-substituted)propylene side-armed derivatives of aza-crown ethers. Stability constants for the complexes of several synthesized lariats with metal cations are discussed.