Direct synthesis of imines from gem-dibromomethylaryl derivatives: application to unsymmetrically substituted bipyridine frameworks.
An efficient methodology for the one-pot synthesis of imines is described starting from gem-dibromomethylaryl compounds and primary amines. The synthesis was applied to various aliphatic mono- and polyamines as well as to electron-rich anilines. The protocol was extended to 6-bromo-5'-dibromomethyl-2,2'-bipyridine to afford the corresponding imines. With n-propyl- and n-decylamine, further conversion, in three steps, to the corresponding 6-carboxy-5'-alkylaminomethyl-2,2'-bipyridine derivatives was selectively achieved, providing new tridentate ligands that may find interesting applications for the complexation of lanthanide(III) cations in their anionic or zwitterionic form.
Weibel
Nicolas
N
Laboratoire de Chimie Moléculaire, UMR 7008 au CNRS, Ecole de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
Charbonnière
Loïc J
LJ
Ziessel
Raymond F
RF