Synthesis and conformational properties of 2,6-bis-anilino-3-nitropyridines

Org Biomol Chem. 2005 Sep 21;3(18):3408-21. doi: 10.1039/b508819b. Epub 2005 Aug 17.

Abstract

The synthesis of 2,6-bis-anilino-3-nitropyridines that are alkylated or acylated at the anilino nitrogen atoms is described. These derivatives show characteristic differences in the 1H-NMR spectra compared with the unsubstituted parent compound. These differences are used to determine structure-conformation relationships of this type of compounds. The conclusions drawn from the 1H-NMR spectra in this respect are supported by X-ray crystallographic data and by 1H-NMR data of conformationally restricted analogues. Preliminary investigations indicate that these relationships can in principle be extended to other diarylamines.