Microwave Irradiation Syntheses and Crystal Structures of Two Series of Novel Five- Membered Heterocyclic Mono-Imine Compounds

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Author(s): Biyun Su*, Yaning Li, Dandan Pan, Paison Faida, Tingyu Yan, Zhan Qu.

Journal Name: Current Organic Synthesis

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Aim and Objective: The late transition metal complexes with five-membered heterocyclic monoimine ligands have attracted much attention because of their potential application in olefin polymerization catalysis. In order to increase the coordination ability of heteroatom N and S to center metals, CH3 group was introduced into the side arm of pyrrole imine and thiophene imine respectively, to get two series of novel fivemembered heterocyclic imine compounds, mono (imino)pyrroles and mono(imino)-thiophenes.

Materials and Methods: Two series of novel five-membered heterocyclic compounds with the mono-imine group were synthesized from the p-toluene sulfonic acid catalyzed Schiff base condensation of aromatic amines and 2-acetylpyrrole/ 2-acetylthiophene respectively, using CH3 group to substitute the common H atom on the side arm of pyrrole imine/ thiophene imine.

Results: All the heterocyclic mono-imine compounds were characterized adequately by means of 1H NMR, 13C NMR, FT-IR, elementary analysis, as well as X-ray crystallographic diffraction. The reactivity differences between two precursor 2-acetylpyrrole and 2-acetylthiophene with aromatic amines were compared and discussed in detail.

Conclusion: Compared to traditional heating methods, the solvent-free microwave irradiation seemed more efficient to prepare these series of five-membered heterocyclic mono-imine compounds, which resulted in a higher yield and cleaner product.

Keywords: Mono-imine compounds, microwave irradiation, Schiff base condensation, crystal structures.

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(E-pub Ahead of Print)
DOI: 10.2174/1570179416666181207125604
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