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

Background Nowadays, macrocyclic compounds constitute a privileged source for the development of compounds with interesting biological properties. Ring-closing olefin metathesis has received great attention for the synthesis of small, medium, and larger ring systems.Materials and Methods In the present work, we described the synthesis of eight original pyridyl macrocyclic triarylmethanes using an efficient 3-step 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.Results 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 a 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.Conclusion The synthetic strategy used here proposes an efficient alternative to prepare macrocyclic triarylmethanes of different sizes.