An Alternative Synthetic Approach to 3-Alkylated/Arylated 5-Nitropyridines

J Org Chem. 2015 Sep 4;80(17):8856-8. doi: 10.1021/acs.joc.5b01391. Epub 2015 Aug 19.

Abstract

An alternative method for the synthesis of 3-alkylated/arylated 5-nitropyridines was developed involving a three-component ring transformation of 3,5-dinitro-2-pyridone on treatment with aldehyde in the presence of ammonium acetate. This method facilitates the modification of the substituent at the 3-position by changing the precursor aldehyde. The use of solid ammonium acetate instead of ammonia as the nitrogen source renders the synthetic method more practical and user-friendly.

Publication types

  • Research Support, Non-U.S. Gov't