Specific and selective reduction of aromatic nitrogen heterocycles with the bis-pyridine complexes of bis(1,4-dihydro-1-pyridyl)zinc and bis(1,4-dihydro-1-pyridyl)magnesium

Abstract

Aromatic nitrogen heterocycles, e.g. quinoline, 2,2‘-bipyridyl and 1,10-phenanthroline, are reduced in a uniquely specific and selective way by the bispyridine complexes of bis(1,4-dihyro-1-pyridyl)zinc and bis(1,4-dihydro-1-pyridyl)magnesium. The reactions occur by hydrogen transfer from the metal-bound 1,4-dihydropyridyl moieties to the substrates and yield zinc or magnesium salts of the 1,4-dihydroazaaromatic derivatives. Upon hydrolysis, the 1,4-dihydroazaaromatic compounds are liberated from the metal ions. The isolation and purification of several of the (novel) reduced compounds, e.g. 1,4-dihydroquinoline and 1,4-dihydro-1,10-phenanthroline, are described.