Abstract
A one-pot catalytic three-component synthesis of 7-amino-1,3-dioxo-1,2,3,5-tetrahydropyrazolo[1,2-a][1,2,4]triazole derivatives from arylaldehydes, 4-phenylurazole, and malononitrile by employing magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst is described. This green and nano-catalytic procedure showed good recyclability and provides cleaner conversion in a short reaction time. These advantages make the protocol feasible and economical attractive for researchers.
Similar content being viewed by others
References
A. Tiwari, A.K. Mishra, H. Kobayashi, A.P.F. Turner, Intelligent nanomaterials (Wiley, New York, 2012)
C.N.R. Rao, A. Müller, A.K. Cheetham, The chemistry of nanomaterial, vol. 1. (Wiley-VCH, Weinheim, 2006)
K.J. Klabunde, R.M. Richards, Nanoscale materials in chemistry (Wiley, New York, 2009)
C.N.R. Rao, A. Müller, K. Anthony, Cheetham nanomaterials chemistry: recent developments and new directions (Wiley, New York, 2007)
M.Z. Kassaee, H. Masrouri, F. Movahedi, Appl. Catal. A Gen. 395, 28–33 (2011)
H. Yarahmadi, H.R. Shaterian, J. Chem. Res. 36, 49–51 (2012)
N. Haddad, A. Salvango, C. Busacca, Tetrahedron Lett. 45, 5935–5937 (2004)
A. Tanitame, Y. Oyamada, K. Ofugi, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, M.J.I. Yamagishi, J. Med. Chem. 47, 3693–3696 (2004)
F. Varano, D. Catarzi, V. Colotta, O. Lenzi, G. Filacchioni, A. Galli, C. Costagli, Bioorg. Med. Chem. 16, 2617–2626 (2008)
J. Bailey, J. Chem. Soc. Perkin Trans. 118, 2047–2054 (1977)
G. Plos, A. Lagrange, Eur. Pat. Appl. Patent EP 1062937 (2000)
H.R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 158, 145–150 (2011)
H.R. Shaterian, M. Ranjbar, K. Azizi, J. Mol. Liq. 162, 95–99 (2011)
H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40–49 (2011)
M.R. Liane, A.S.G. Marco, L.R.V. Lucas, J. Braz. Chem. Soc. 23, 1959–1971 (2012)
R.B. Nasir Baig, S.V. Rajender, Chem. Commun. 49, 752–770 (2013)
S.J. Hoseini, H. Nasrabadi, M. Azizi, A. Salimi Beni, R. Khalifeh, Synth. Commun. 43, 1683–1691 (2013)
B. Karami, S.J. Hoseini, K. Eskandari, A. Ghasemi, H. Nasrabadi, Catal. Sci. Technol. 2, 331–338 (2012)
B.V. Subba Reddy, A. Siva Krishna, A.V. Ganesh, G.G.K.S. Narayana Kumar, Tetrahedron Lett. 52, 1359–1362 (2011)
D. Azarifar, R.N. Yami, Heterocycles 81, 2063–2073 (2010)
Acknowledgment
We are grateful to the University of Sistan and Baluchestan Research Council for the partial support of this research.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shaterian, H.R., Moradi, F. Preparation of 7-amino-1,3-dioxo-1,2,3,5-tetrahydropyrazolo [1,2-a][1,2,4]triazole using magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst. Res Chem Intermed 41, 223–229 (2015). https://doi.org/10.1007/s11164-013-1184-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-013-1184-2