Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates

Monatsh Chem. 2018;149(4):715-719. doi: 10.1007/s00706-017-2081-y. Epub 2017 Nov 28.

Abstract

Abstract: A regioselective synthesis of pyridines by the addition of malonate anions to pyridine N-oxide derivatives, which have been activated by trifluoromethanesulfonic anhydride, is reported. The reaction selectively affords either 2- or 4-substituted pyridines in good yields.

Keywords: Heterocycles; Nucleophilic additions; Umpolung.