Diastereoselective Synthesis of Symmetrical and Unsymmetrical Tetrahydropyridines Catalyzed by Bi(III) Immobilized on Triazine Dendrimer Stabilized Magnetic Nanoparticles

ACS Comb Sci. 2017 Jun 12;19(6):356-364. doi: 10.1021/acscombsci.6b00180. Epub 2017 May 22.

Abstract

Unsymmetrical 1,2,5,6-tetrahydropyridine-3-carboxylates were obtained for the first time from a five-component Fe3O4@TDSN-Bi(III)-catalyzed reaction of aryl aldehydes, aryl amines, and ethyl acetoacetate. This magnetically separable catalyst enabled the selective incorporation of two different aryl amines or two different aryl aldehydes into the product, and provided excellent yields, short reaction times, mild reaction conditions, satisfactory catalyst recyclability, and low catalyst loading.

Keywords: Fe3O4 NPs; diastereoselective; multicomponent reactions (MCRs); tetrahydropyridine; triazine dendritic polymer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bismuth / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Dendrimers / chemistry*
  • Magnetite Nanoparticles / chemistry*
  • Models, Molecular
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Stereoisomerism
  • Triazines / chemistry*

Substances

  • Dendrimers
  • Magnetite Nanoparticles
  • Piperidines
  • Triazines
  • 1-piperideine
  • Bismuth