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

Abstract

Background:: Nowadays, macrocyclic compounds constitute a privileged source for the development of compounds with interesting biological properties. Ring-closing olefin me-tathesis has received great attention for the synthesis of small, medium, and larger ring systems. 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 interest-ing 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 macro-cyclic triarylmethanes of different sizes.