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

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

Journal Name: Current Organic Synthesis

Volume 16 , Issue 3 , 2019

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Graphical Abstract:


Aim and Objective: The late transition metal complexes with five-membered heterocyclic mono-imine 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 five-membered 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, heterocyclic ligands, aromatic amines.

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Article Details

Year: 2019
Page: [444 - 448]
Pages: 5
DOI: 10.2174/1570179416666181207125604
Price: $58

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