Novel Pyridyl Macrocyclic Triarylmethanes: Synthesis by Ring-Closing Metathesis and Chemical Analysis

Abstract

In the present work, we described the synthesis of eight original pyridyl macrocyclic triarylmethanes using an efficient 3-steps synthetic strategy. The bisalkylated 4,4'-(pyridin-X-ylmethylene) diphenols (X=2-4) were prepared by ring-closing metathesis, as macrocyclization key step, using Grubbs second generation catalyst. The pyridyl macrocyclic triarylmethanes were obtained with moderate to good yields. The introduction of a pyridine N-oxide moiety before the macrocyclization proved to be interesting to afford higher yield of the corresponding metathesis product.  FT-IR, 1 H NMR, 13C NMR and  X-Ray diffraction analysis have been used for the characterization of the synthesized compounds.

Keywords: Ring closing metathesis * triarylmethanes * macrocyclization * Grubb's catalysis * Pyridine N-oxide