Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds

Org Biomol Chem. 2004 Mar 7;2(5):788-96. doi: 10.1039/b315689c. Epub 2004 Feb 11.


alpha-hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modifications to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.