Novel phosphonated bicyclic frameworks from Diets-Alder reaction as chelating agents of di- and trivalent metal cations

The synthesis of novel [4+2] cycloadducts by Diels-Alder (DA) reaction between diethyl 1-phosphono-1,3-butadiene and cyclic C=C and N=N dienophiles, such as maleimide and 1,2,4-triazole-3,5-dione derivatives, is described. These phosphonated bicyclic frameworks feature a cage shape enabling metal chelation. Indeed, stable complexes were formed in solution with M(2+) and M(3+) metal cations, as evidenced by HRMS in the ESI mode (electrospray ionization). L(1):M (one ligand-one metal) and L(2):M (two ligands-one metal) complexes were identified depending on the nature of the cation. (C) 2011 Elsevier Ltd. All rights reserved.