Mild preparation of hydroxyl naphthalene-1,4-dione
derivatives with nano copper(II) oxide as catalyst
under ambient and solvent-free conditions
Hamid Reza Shaterian
Received: 3 February 2013 / Accepted: 4 April 2013 / Published online: 18 April 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract An efﬁcient one-pot quantitative procedure for the preparation of
hydroxyl naphthalene-1,4-dione derivatives from three-component condensation
reaction of aromatic aldehydes, aromatic amines, and 2-hydroxynaphthalene-1,4-
dione in the presence of nano copper(II) oxide as catalyst under mild, ambient and
solvent-free conditions is described. Simple procedure, high yields, short reaction
time and an environmentally benign method are advantages of these protocols. The
copper(II) oxide nanoparticles can be recovered and reused several times without
loss of its activity.
Keywords Nanoparticles Á Copper(II) oxide Á Aldehyde Á
2-Hydroxynaphthalene-1,4-dione Á Amine Á Solvent-free
Nanomaterials have attracted a great deal of attention in organic synthesis owing to
their high surface-to-volume ratios, which are responsible for the higher catalytic
activity . The catalytic activity of the nano CuO and its applications exhibit good
reusability, simple workup procedure and a straightforward approach to use in
organic synthesis [2–4].
Multi-component reactions (MCRs) have proven to be a valuable asset in organic
and medicinal chemistry as such protocols can be used for drug design and drug
discovery because of their simplicity, efﬁciency, and high selectivity [5, 6].
Synthesis of bioactive and complex molecules should be easy, fast, and efﬁcient
with minimal workup in this methodology [5–7].
H. R. Shaterian (&) Á F. Moradi
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan,
PO Box 98135-674, Zahedan, Iran
Res Chem Intermed (2015) 41:291–297