Journal of Molecular Liquids 218 (2016) 558–564
Contents lists available at ScienceDirect
Journal of Molecular Liquids
A convenient method for the synthesis of 1,8-dioxodecahydroacridine
derivatives using 1-methylimidazolium tricyanomethanide
{[HMIM]C(CN)3} as a nanostructured molten salt catalyst
⁎
Mohammad Ali Zolfigol , Neda Bahrami-Nejad, Saeed Baghery
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
A practical and convenient method for the synthesis of 1,8-dioxodecahydroacridine derivatives was achieved via
the one-pot condensation reaction of cyclic 1,3-diketone, aldehydes and various anilines or ammonium acetate in
the presence of 1-methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a nanostructured molten salt
(NMS) catalyst at room temperature. In the present work, more than thirty products will be reported for the
first time.
Received 13 August 2015
Accepted 2 March 2016
Available online xxxx
Keywords:
© 2016 Elsevier B.V. All rights reserved.
1-Methylimidazolium tricyanomethanide
1,8-Dioxodecahydroacridine
Nanostructure molten salt
Solvent-free conditions
1. Introduction
Recently, the first nano ionic liquid (NILs) and nano molten salts
(NMSs) have been reported by our research group and there have
Nowadays, one-pot multi-component reactions (MCRs) are more
demand due to the benefit of their convergence, efficiency, facile perfor-
mance and high yield [1]. There has been an enormous development in
multi-component reactions (MCRs), particularly the Ugi [2], Passerini
[3], Bignelli [4] and Mannich [5] reactions. Great effort is needed to find
new MCRs and/or to modify the previously known reported procedures.
One such reaction is the synthesis of 1,8-dioxodecahydroacridines.
Throughout the recent years, great attention has been paid to the syn-
thesis of 1,8-dioxodecahydroacridines because of their highly complete
physiological and biological activities for example antimicrobial [6],
anti-multidrug-resistant [7], anti-tumor [8], cytotoxic [9], anti-cancer
[10] and anti-fungal properties [11]. These compounds are commonly
synthesized in a three-component reaction of 1,3-diketone, aldehydes
and various anilines or ammonium acetate using several catalysts for
example [2-MPyH]OTf [12], Cu(II) Schiff base [13], Fe3O4 nano particles
[14], amberlyst-15 [15], silica-bonded N-propyl sulfamic acid (SBNPSA)
[16], ceric ammonium nitrate (CAN) [17], 4-dodecylbenzenesulfonic
acid (DBSA) [18] and proline [19].
Molten salts (MSs), ionic liquids (ILs) and room temperature ionic
liquids (RTILs) are particularly combined of suitable cations and anions.
Typically, ionic liquids (ILs) and molten salts (MSs), refer to organic
onium salts which molten below and above 100 °C respectively [20].
MSs are an noteworthy class of liquids because of their unique ionic
interactions and their broad number of scientific uses [21]. MSs have
significant potentials for various purposes [22–24]. MSs and ILs can be
engaged as a GC immobile phases for both packed and open-tubular
columns [25–28].
been also used as nano catalysts in a good range of organic reactions
[29]. Therefore, as a part of our continuous study to the design, synthesis
and application of homogeneous catalysts such as nano catalysts in
organic synthetic procedures [30], herein, we wish to report an efficient
method for synthesis of 1,8-dioxodecahydroacridine derivatives in the
presence of 1-methylimidazolium tricyanomethanide {[HMIM]C(CN)3}
as a green, recycle and reusable nanostructured molten salt(NMS)
catalyst under solvent-free conditions via condensation of 1,3-diketone,
aldehydes and various anilines or ammonium acetate (Scheme 1).
2. Experimental
2.1. General procedure for the preparation of nano structure molten salt
catalyst: 1-methylimidazolium tricyanomethanide
The nanostructured molten salt {[HMIM]C(CN)3} as a catalyst was
synthesized according to our previously reported procedure [29]. A
pale pink solid was prepared in high purity which its physical data is
as same as those reported data in the literature. M.p: N300 °C; yield:
96% (0.498 g); spectral data: IR (KBr): υ 3417, 2925, 2170, 2081, 1631,
1574, 1455 cm−1 1H NMR (400 MHz, DMSO-d6): δ 3.63 (s, 3H,
;
\\CH3), 7.00 (s, 2H,\\CH); 7.63 (s, 1H,\\CH), 11.95 (brs, 1H,\\NH);
13C NMR (100 MHz, DMSO-d6): δ 46.4, 67.2, 74.8, 119.8, 134.9, 160.2;
MS: m/z = 173 [M]+.
0167-7322/© 2016 Elsevier B.V. All rights reserved.