Metal complexes of 4,6-O-ethylidene-β-d-glucopyranosylamine derivatives and their application in organic synthesis

Abstract

Glycosylamine derivatives of 4,6-O-ethylidene-d-glucose have been used for complexing the alkali, alkaline earth and transition metal ions. Three different series of ligands have been reported where N-(o-carboxyphenyl)-4,6-O-ethylidene-β-d-glucopyranosylamine has been used for complexing the diamagnetic (Li+, Na+, K+, Mg2+, Ca2+, Ba2+, Zn2+, Cd2+, Hg2+) metal ions. N-(2-Hydroxybenzoyl)-L-alanyl-4,6-O-ethylidene-β-d-glucopyranosylamine selectively interacts with molecular cupric acetate and the adduct acts as a catalyst in selective oxidation of primary and secondary alcohols into their corresponding carbonyl compounds. Salicylidene derivatives of 4,6-O-ethylidene-β-d-glucopyranosylamine have been used in complexing Ni2+, Cu2+, Zn2+, VO2+, MoO22+ and UO22+ metal ions, where Cu(II) and Mo(VI) complexes have been further used in the organic synthesis. Dinuclear copper complex exhibited catecholase like activity and also catalyzed the oxidation of primary and secondary alcohols selectively into their corresponding carbonyl compounds. Trinuclear copper complex has been reported to activate the C–Cl bond of solvent chloroform in the presence of mild organic bases below room temperature. Mo(VI) complex has been used as a catalyst for epoxidation, organic sulfide oxidation and synthesis of bis(indolyl)methanes.