Display options
Share it on

ChemistryOpen. 2015 Aug 19;5(1):38-42. doi: 10.1002/open.201500159. eCollection 2016 Feb.

Ceria-Vanadia/Silica-Catalyzed Cascade for C-C and C-O Bond Activation: Green One-Pot Synthesis of 2-Amino-3-cyano-4H-pyrans.

ChemistryOpen

Surya Narayana Maddila, Suresh Maddila, Werner E van Zyl, Sreekantha B Jonnalagadda

Affiliations

  1. School of Chemistry & Physics University of KwaZulu-Natal Westville Campus Chiltern Hills Durban 4000 South Africa.

PMID: 27308209 PMCID: PMC4906492 DOI: 10.1002/open.201500159

Abstract

We designed a ceria-vanadia/silica (Ce-V/SiO2) heterogeneous catalyst and used it for the green and efficient synthesis of 2-amino-3-cyano-4H-pyran derivatives. The green reaction was a multicomponent one-pot condensation of 5,5-dimethylcyclohexane-1,3-dione, aromatic aldehyde, and malononitrile in an eco-compatible solvent (ethanol). The catalyst was synthesized and fully characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), and Brunauer-Emmett-Teller (BET) surface area analysis. The reported procedure offers a number of advantages including decreased reaction times, mild conditions, high yields, operational simplicity, and environmentally benign and simple work-up procedures. Furthermore, the catalyst is economical, fully recyclable, and reusable for over five runs while preserving its high activity. The synthesized 2-amino-3-cyano-4H-pyran products can later be used for pharmaceutical purposes.

Keywords: 4H-pyrans; ceria–vandia/silica (Ce–V/SiO2); green chemistry; heterogeneous catalysts; one-pot multicomponent reactions; recyclable

References

  1. Clin Neuropathol. 2006 Jul-Aug;25(4):163-71 - PubMed
  2. Chem Rev. 1997 Apr 1;97(2):449-472 - PubMed
  3. J Org Chem. 2009 Jun 5;74(11):4372-4 - PubMed
  4. Chemistry. 2008;14(21):6329-32 - PubMed
  5. J Am Chem Soc. 2004 Jul 14;126(27):8390-1 - PubMed
  6. Int Immunopharmacol. 2007 Feb;7(2):222-9 - PubMed
  7. Acta Pharm. 2004 Mar;54(1):13-26 - PubMed
  8. ChemistryOpen. 2015 Aug 19;5(1):38-42 - PubMed
  9. Eur J Med Chem. 2014 Jul 23;82:281-92 - PubMed
  10. Arch Pharm (Weinheim). 2012 Feb;345(2):163-8 - PubMed
  11. Chem Rev. 2009 Sep;109(9):4140-82 - PubMed
  12. Molecules. 2012 Apr 10;17(4):4300-12 - PubMed

Publication Types