N,N′-Bis(2-pyridyl)benzene-1,2-diamine

Abstract

Hindered rotation about the partial double C-N bonds between the amine and pyridine moieties in the title molecule, C16H14N4, results in two different conformations of the N-aryl-2-aminopyridine units. One, assuming an E conformation, is involved in a pair of N-H...N hydrogen bonds that generate a centrosymmetric R2(2)(8) motif. The second, adopting a Z conformation, is not engaged in any hydrogen bonding and is flattened, the dihedral angle between the benzene and pyridine rings being 12.07 (7) degrees. This conformation is stabilized by an intramolecular C-H...N interaction [C...N = 2.9126 (19) A, H...N = 2.31 A and C-H...N = 120 degrees ].

Evaluation of Hydrogen-Bond Acceptors for Redox-Switchable Resorcin[4]arene Cavitands

“…Compound 16 , in turn, was obtained in a one-pot sequence from 1-octylimidazole ( 17 ) via stannylation to stannane 18 and Stille coupling with dibromide 19 . Precursors 12 and 13 were accessed from compound 20 and pyrazines 21 and 22 , respectively. Toward precursor 9b , dibromide 19 was reacted in a Pd-catalyzed aminocarbonylation reaction with n Bu 2 NH and CO, affording compound 23 .…”

A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents

“…To avoid this complication 1,2-dibromobenzene had to be applied to eventually approach the preparation of 7 . For 8 a reported synthetic procedure was used [ 48 – 49 ] consisting of nucleophilic aromatic substitutions (S N Ar) of benzene-1,2-diamine at 2-chloropyridine ( Scheme 1 ). Once all the different N 1 , N 2 -diarylbenzene-1,2-diamines were prepared a method had to be developed to build up the imidazolium salts by ring closure.…”

1,3-Bis(pyridin-2-yl)-1H-benzimidazol-3-ium tetrafluoridoborate

“…We used the N,N′-bis(2-pyridyl)-benzene-1,2-diamine compound as a starting material for the synthesis of the title compound, a new imidazolium salt. Despite the fact that the synthesis of the starting material N,N′-bis(pyridin-2yl)benzene-1,2-diamine had been reported previously (Gdaniec et al, 2004), we optimized the procedure to obtain a better yield (91 instead of 70%) using the reaction reported in the Experimental section ( Fig. 4) with a microwave technique.…”

“…For pharmaceuticals based on the aniline-pyridine scaffold, see: Kim et al (1996); Wu et al (2001). For the synthesis of the starting material N,N 0 -bis(pyridin-2-yl)benzene-1,2-diamine, see: Gdaniec et al (2004). Hydrogen-bond geometry (Å , ).…”