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

Article abstract of DOI:10.1016/S0022-328X(00)83849-8

Aromatic nitrogen heterocycles, e.g. quinoline, 2,2'-bipyridyl and 1,10-phenanthroline, are reduced in a uniquely specific and selective way by the bis-pyridine complexes of bis(1,4-dihydro-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.