Multicomponent preparation of highly functionalized piperidines using FeCl3.6H2O as an efficient catalyst

Authors

• Jasem Aboonajmi ¹
• Malek Taher Maghsoodlou ²
• Nourallah Hazeri ²
• Mojtaba Lashkari ³
• Mohyeddin Safarzaei ⁴
• Moheb Shirzaei ⁴

1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
2. Chemistry Department, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran
3. Faculty of Science, Velayat University, Iranshahr, Iran.
4. Department of Chemistry, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran.

Abstract

FeCl3.6H2O was used as an efficient catalyst for the synthesis of highly functionalized piperidines via a one-pot five-component reaction of aromatic amines, aromatic aldehydes and β-keto esters in EtOH at room temperature. The remarkable advantages offered by this method are good yields, simple procedure, short reaction times, no need to column chromatography and easy work-up. The structures of all compounds were characterized by comparison of their IR and NMR spectra with authentic samples. Also, the relative stereochemistry of these piperidines has been confirmed by single X-ray crystallography analysis in previously reported literature. Starting materials with electron-deficient or electron-releasing groups were reacted efficiently.

Keywords

• β-Keto ester
• Aldehyde
• Multicomponent
• Functionalized piperidine