Atropisomers of Cofacial Heteroaromatic Rings with Two Positive Charges. Derivatives of 1,8-Di(3'-pyridyl)naphthalene

J Org Chem. 1996 Oct 4;61(20):7018-7021. doi: 10.1021/jo960906g.

Abstract

The two nitrogen atoms in 1,8-di(3'-pyridyl)naphthalene were quaternized by the addition of either benzyl or methyl groups to give dications; the latter was oxidatively converted to the di(6'-pyridone). N-Oxidation gave the mono- and di-N-oxides. All these compounds in DMSO-d(6) show anti-syn atropisomerism at ambient temperatures by (1)H NMR analysis; similar amounts of both diastereomers are present.