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.
Katritzky
Alan R.
AR
Department of Molecular Biology and Pharmacology, Washington University School of Medicine, Washington University, St. Louis, Missouri 63110.
Denisko
Olga V.
OV
Belyakov
Sergei A.
SA
Schall
Otto F.
OF
Gokel
George W.
GW