Pseudo five-component process for the synthesis of functionalized tricarboxamides using CuI nanoparticles as reusable catalyst

Article abstract of DOI:10.1016/j.cclet.2013.01.049

An efficient and multicomponent method has been developed for the synthesis of functionalized tricarboxamides at room temperature using CuI nanoparticles as catalyst. This method involved five-component coupling reactions of Meldrum's acid, isocyanides wi

Full text of DOI:10.1016/j.cclet.2013.01.049

Chinese Chemical Letters 24 (2013) 195–198
Contents lists available at SciVerse ScienceDirect
Chinese Chemical Letters
journal homepage: www.elsevier.com/locate/cclet
Original article
Pseudo five-component process for the synthesis of functionalized
tricarboxamides using CuI nanoparticles as reusable catalyst
*
Abolfazl Ziarati, Javad Safaei-Ghomi , Sahar Rohani
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 51167, Islamic Republic of Iran
A R T I C L E I N F O
A B S T R A C T
Article history:
An efficient and multicomponent method has been developed for the synthesis of functionalized
tricarboxamides at room temperature using CuI nanoparticles as catalyst. This method involved five-
component coupling reactions of Meldrum’s acid, isocyanides with aromatic aldehydes and amines at
room temperature. Atom economy, wide range of products, excellent yields in short time and mild
reaction conditions are some of the important features of this protocol. Notably, this catalyst could be
recycled and reused for several times without significantly decreasing the catalytic activity.
ß 2013 Javad Safaei-Ghomi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights
reserved.
Received 12 November 2012
Received in revised form 9 January 2013
Accepted 16 January 2013
Available online 7 March 2013
Keywords:
Tricarboxamides
Copper iodide nanoparticles
Multicomponent reactions
Reusable catalyst
1. Introduction
can ease their interactions between cells and tissues and thereby
provides a vigorous strategy to produce novel drugs or compounds.
Multicomponent reactions (MCRs) have been proved to be an
efficient method to approach complex structures in a single
synthetic operation from simple building blocks. Advantages of
MCRs are high selectivity, high atom economy, and procedural
simplicity due to the formation of carbon–carbon or carbon–
heteroatombondsinonepot[1,2]. Typically,purificationofproducts
resulting from MCRs is also simple since all the organic reagents are
consumed and converted into the target products [3–7].
Isocyanide-based multi-component reactions (IMCRs) are
specifically interesting as they are more varied and versatile than
other MCRs [8,9]. Isocyanides in multi-component reactions
increase the diversity of available bond forming procedures,
functional group tolerance, and levels of stereo-, chemo-, and
regioselectivity. Therefore MCRs including isocyanides have
emerged as suitable tools for the synthesis of structurally varied
chemical libraries [10–12].
The diversity of the structures encountered, as well as their
pharmaceutical and biological relevance, has motivated research
purposed at the development of convenient and efficient synthetic
strategies, especially for the synthesis of substituted tricarbox-
amide scaffolds [18–22].
The chemical synthesis productivity can be increased by nano
sized catalysts because of small size and high surface to volume
ratios. Moreover, this productivity was improved by using
heterogeneous catalysts for their simplicity of separation [23–27].
Recently, it was reported that CuI nanoparticles as heterogeneous
catalysts offer huge opportunities for a wide range of applications in
chemicalsynthesisand chemicalmanufacturingprocedures [28,29].
In continuation of our efforts to develop syntheses of various
biological compounds using reusable nano catalysts [30–32], we
report here the use of CuI nanoparticles catalyzed five-component
synthesis of tricarboxamides in mild conditions (Scheme 1).
On the other hand, tricarboxamides and their analogs have
displayed a wide range of important bioactivities, such as anti-tumor
[13], anti-bacterial [14], anti-diabetic [15], neuroprotective [16] and
anti-carcinogenic properties [17]. Carboxamides segments have an
affinity tonucleicacids andcells,sotheirintroductionintomedicines
2. Experimental
2.1. Preparation of copper iodide nanoparticles
The catalyst was prepared by ultrasonic irradiation. CuSO4 was
used as the Cu source. Firstly, the copper substrate (1 mmol) was
ultrasonically cleaned for 20 s in acetone followed by repeated
rinsing with distilled water. After drying, the substrate was dipped
slowly into a solution of KI (1 mmol) in 40 mL of distilled water and
* Corresponding author.
E-mail address: safaei@kashanu.ac.ir (J. Safaei-Ghomi).
1001-8417/$ – see front matter ß 2013 Javad Safaei-Ghomi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
http://dx.doi.org/10.1016/j.cclet.2013.01.049

196
CHO
A. Ziarati et al. / Chinese Chemical Letters 24 (2013) 195–198
NH2
Table 1
Optimization of model reaction.
R1
O
Entry
Solvent/condition
Catalyst (mol%)
Time (h)
Yield (%)a
+
H
N
R3
R2
R1
1
2
MeCN/rt
CH2Cl2/rt
H2O/rt
CuI (12%)
10
10
10
10
10
10
9
62
87
31
88
89
54
82
81
85
94
98
98
4
1
CuI (12%)
nano CuI
EtOH, rt
O
O
R3-N
3
C
O
3
CuI (12%)
4
MeOH/rt
EtOH/rt
EtOH/reflux
EtOH/rt
EtOH/rt
EtOH/rt
EtOH/rt
EtOH/rt
EtOH/rt
CuI (12%)
NH2
NH HN
O
5
CuI (12%)
R2
R2
6
CuI (12%)
+
O
O
7
None
5a-r
8
MgO (15%)
InCl3 (20%)
Nano CuI (1%)
Nano CuI (2%)
Nano CuI (3%)
10
10
4
R2
9
4
2
10
11
12
4
Scheme 1. Synthesis of tricarboxamides using CuI nanoparticles as catalyst.
4
a
Isolated yields.
sonicated to react for 30 min. When the reaction was completed,
gray precipitate was obtained. The solid was filtered and washed
with distilled water and dried.
To obtain a visual image of this catalyst, powder X-ray
diffraction (XRD) and scanning electron microscopy (SEM) was
carried out (see Figs. S1 and S2 in supporting information). As
shown in the XRD pattern, all reflection peaks can be readily
indexed to pure cubic crystal phase of nanocrystalline copper
iodide. Crystallite size of CuI has been found to be 20 nm, which
FT-IR (KBr, cmꢀ1):
(400 MHz, DMSO-d6):
NCH), 3.82 (d, 1H, J = 9.7 Hz, CH), 4.18 (d, 1H, J = 9.7 Hz, CH), 7.02–
7.64 (m, 12H, Ar), 8.12 (brs, 1H, NH), 9.60 and 9.74 (2s, 2H, 2 NH);
13C NMR (100 MHz, DMSO-d6):
148.7, 145.4, 145.1, 129.9, 126.7, 125.4, 124.1, 122.9, 121.6, 118.5,
63.7, 50.1, 46.9, 33.7, 33.4, 26.4. Anal. Calcd. for C31H34N4O7: C,
64.81; H, 5.92; N, 9.76. Found: C, 64.55; H, 5.72; N, 9.94. MS (EI) (m/
z): 574 (M+).
n
3288, 3268, 1682, 1650, 1617; 1H NMR
1.10–1.58 (m, 10H, 5CH2), 3.59 (s, 1H,
d
d 173.2, 168.6, 167.1, 150.6, 149.8,
was calculated by the Debye-Scherrer equation (D = Kl/bcos u)
and confirmed by SEM. The increased surface area due to small
particle size increased reactivity. This factor is responsible for the
accessibility of the substrate molecules on the catalyst surface.
In addition, the specific surface area was measured by nitrogen
physisorption (the BET method), the specific surface area was
approximately 2.94 m2/g.
1
2
2
0
N -tert-Butyl-N ,N -bis(4-chlorophenyl)-1-phenylethane-1,2,2-
tricarboxamide (5k): White solid; mp 317–319 8C, FT-IR (KBr,
cmꢀ1):
d6):
1H, J = 10.6 Hz, CH), 7.09–7.63 (m, 13H, Ar), 8.32 (s, 1H, NH), 9.58
and 9.79 (2s, 2H, 2 NH); 13C NMR (100 MHz, DMSO-d6):
173.4,
n
3301, 3287, 1678, 1647, 1636; 1H NMR (400 MHz, DMSO-
1.18–1.27 (s, 9H, 3CH3), 3.77 (d, 1H, J = 10.5 Hz, CH), 4.19 (d,
d
d
2.2. General procedure for the preparation of tricarboxamides (5a–r)
168.1, 166.9, 151.2, 151.0, 147.6, 147.1, 129.8, 128.1, 125.9, 125.5,
124.8, 122.8, 121.7, 119.2, 62.1, 49.6, 46.3, 29.9. Anal. Calcd. for
A solution of aldehyde (2 mmol), Meldrum’s acid (2 mmol), CuI
nanoparticles (2 mol%) and ethanol (4 mL) was stirred for 30 min.
Then, cyclohexyl isocyanide (2 mmol) and amine (4 mmol) was
added and vigorously stirred for the appropriate time (Table 1,
monitored by TLC). After completion of reaction, the solid was
filtered off and washed with chloroform. The residue was dissolved
in hot methanol and then filtered until the heterogeneous catalyst
was recovered. The filtrate solution was recrystallized to afford the
pure product in 89%–98% yield.
C
27H28Cl2N3O3: C, 64.62; H, 5.18; N, 7.88. Found: C, 63.65; H, 5.11;
N, 7.98. MS (EI) (m/z): 511 (M+).
1
2
2
0
N -tert-Butyl-N ,N -bis(4-bromophenyl)-1-(4-chloropheny-
l)ethane-1,2,2-tricarboxamide (5p): Yellowish solid; mp 320–
322 8C, FT- IR (KBr, cmꢀ1):
NMR (400 MHz, DMSO-d6):
n
d
3296, 3258, 1688, 1651, 1617; 1H
1.21–1.29 (s, 9H, 3CH3), 3.81 (d, 1H,
J = 11.0 Hz, CH), 4.16 (d, 1H, J = 10.9 Hz, CH), 7.09–7.73 (m, 12H,
Ar), 8.16 (s, 1H, NH), 9.68 and 9.81 (2s, 2H, 2 NH); 13C NMR
(100 MHz, DMSO-d6):
147.5, 146.2, 128.8, 127.5, 126.3, 124.8, 123.1, 122.0, 118.9, 62.7,
50.1, 46.3, 29.2. Anal. Calcd. for C27H27Br2ClN3O3: C, 51.03; H, 4.18;
N, 6.61. Found: C, 52.37; H, 4.12; N, 6.48. MS (EI) (m/z): 633 (M+).
d 173.7, 167.8, 167.1, 151.9, 151.0, 148.3,
2
2
0
1
N ,N -Bis(4-chlorophenyl)-N -cyclohexyl-1-phenylethane-1,2,2-
tricarboxamide (5b): White solid; mp 309–311 8C, FT- IR (KBr,
cmꢀ1):
d6):
n
3280, 3262, 1681, 1643, 1607; 1H NMR (400 MHz, DMSO-
0
d
1.11–1.62 (m, 10 H, 5CH2), 3.52 (s, 1H, NCH), 3.81 (d, 1H,
N1-tert-Butyl-N2,N2 -bis(4-methoxyphenyl)-1-(4-nitropheny-
J = 11.2 Hz, CH), 4.14 (d, 1H, J = 11.2 Hz, CH), 6.99–7.51 (m, 13H,
l)ethane-1,2,2-tricarboxamide (5r): Yellowish solid; mp 329–
Ar), 8.21 (brs, 1H, NH), 9.62 and 9.75 (2s, 2H, 2 NH); 13C NMR
331 8C, FT-IR (KBr, cmꢀ1): 3296, 3271, 1690, 1664, 1621; 1H
NMR (400 MHz, DMSO-d6): d 1.20–1.32 (s, 9H, 3CH3), 3.86 (d, 1H,
n
(100 MHz, DMSO-d6):
d
173.2, 168.6, 167.1, 151.6, 150.9, 147.3,
147.1, 129.7, 128.3, 126.1, 125.6, 124.5, 122.3, 121.9, 118.7, 62.5,
49.4, 46.2, 33.4, 33.1, 26.8. Anal. Calcd. for C29H29Cl2N3O3: C, 64.68;
H, 5.39; N, 7.81. Found: C, 63.77; H, 5.16; N, 7.93. MS (EI) (m/z): 537
(M+).
J = 8.1 Hz, CH), 4.22 (d, 1H, J = 8.1 Hz, CH), 7.05–7.61 (m, 12H, Ar),
8.11 (s, 1H, NH), 9.57 and 9.76 (2s, 2H, 2 NH); 13C NMR (100 MHz,
DMSO-d6):
d 172.6, 168.9, 167.3, 151.1, 149.6, 148.8, 145.2, 145.1,
129.4, 126.3, 125.1, 124.5, 123.3, 121.2, 118.7, 63.9, 50.4, 46.7, 29.5.
Anal. Calcd. for C29H33N4O7: C, 63.49; H, 5.88; N, 10.21. Found: C,
64.11; H, 5.78; N, 9.95. MS (EI) (m/z): 548 (M+).
2
2
0
1
N ,N -Bis(4-bromophenyl)-1-(4-chlorophenyl)-N -cyclohexy-
lethane-1,2,2-tricarboxamide (5g): White solid; mp 314–318 8C, FT-
IR (KBr, cmꢀ1): 3287, 3265, 1680, 1646, 1611; 1H NMR (400 MHz,
n
DMSO-d6):
d
1.13–1.57 (m, 10H, 5CH2), 3.55 (s, 1H, NCH), 3.79 (d,
3. Results and discussion
1H, J = 11.4 Hz, CH), 4.17 (d, 1H, J = 11.3 Hz, CH), 7.06–7.68 (m,
12H, Ar), 8.19 (brs, 1H, NH), 9.63 and 9.77 (2s, 2H, 2 NH); 13C NMR
In our initial experiments, the model reaction conditions were
established based on the reactions between benzaldehyde
(2 mmol), 4-chloroaniline (4 mmol), cyclohexyl isocyanide
(2 mmol) and Meldrum’s acid (2 mmol) in different solvents and
catalysts. This reaction was carried out using the aprotic (Table 1,
entries 1 and 2) and protic solvents (Table 1, entries 3–5). The best
result was obtained in ethanol (Table 1, entry 5). Next, we studied
the model reaction in ethanol at different temperatures (Table 1,
(100 MHz, DMSO-d6):
d 173.4, 168.1, 167.5, 151.8, 151.2, 148.0,
147.8, 146.5, 129.2, 127.4, 125.9, 124.3, 122.7, 122.1, 118.6, 62.6,
49.8, 46.7, 33.5, 33.0, 27.0. Anal. Calcd. for C29H28Br2ClN3O3: C,
52.60; H, 4.23; N, 6.35. Found: C, 52.43; H, 4.16; N, 6.51. MS (EI) (m/
z): 659 (M+).
2
2
0
1
N ,N -Bis(4-methoxyphenyl)-1-(4-nitrophenyl)-N -cyclohexy-
lethane-1,2,2-tricarboxamide (5i): Yellowish solid; mp 323–325 8C,

A. Ziarati et al. / Chinese Chemical Letters 24 (2013) 195–198
197
Fig. 1. TEM images of nano CuI before used (a), after four uses (b).
entries 5 and 6). The maximum yield was obtained at room
temperature (Table 1, entry 5). The model reaction in ethanol at
room temperature was also studied in absence of catalyst and
using other types of catalysts (Table 1, entries 6–12). Although in
the absence of catalyst, the reaction was carried out but in the
presence of CuI nanoparticle we observed higher yield of product
in shorter time (Table 1, entry 7). We believe that nano copper
iodide surface chemistry plays an important role in this reaction.
The best results were obtained with 2 mol% of nano CuI (Table 1,
entry 11).
and isocyanides. Three substituents in the products could be varied
freely of each other. The results were summarized in Table 2.
Aromatic aldehydes and amines possessing both electron-
withdrawing and electron-donating substituents were converted
into the corresponding tricarboxamides in good yields. In fact, the
reaction was carried out well with all aldehydes and amines.
However, aromatic aldehydes with low steric hindrance, and
amines involving withdrawing groups showed excellent reactivity
in this approach. Using benzaldehyde, 4-chloroaniline and
cyclohexyl isocyanide gave the best yield (98%).
The same reaction was carried out many times in a row to check
the reusability of catalyst. The catalyst could be reused four times
with a minimal loss of activity (see Fig. S3 in supporting
information). The characterization of the nano CuI before used
and after four times reused, showed the same particle size by TEM
(Fig. 1.). Interestingly, the shape and size of the nanoparticles
remained the same before and after the reactions. We believe that,
this is also the possible reason for the extreme stability of the CuI
nanoparticles presented herein.
A proposed mechanism for this five-component reaction was
outlined in Scheme 2 [19]. The first step of this reaction could be
considered as nano CuI catalyzed Knoevenagel condensation
between aldehyde 1 and Meldrum’s acid 2 to afford intermediate
6. Then 6 reacted with cyclohexyl isocyanide 3 following by a [1+4]
cycloaddition, to give iminolactone 7 [33,34].
It was known that acylated Meldrum’s acid readily was
transformed into
b-ketoamide by aminolysis [35]. Correspondingly,
We have shown this reaction is possible under similar
conditions with a wide range of aromatic aldehydes, amines,
R1
O
O
O
O
O
CuI nano
O
O
Table 2
R1
Synthesis of tricarboxamides using CuI nanoparticles.a
O
CHO
1
2
o
Entry
R1
R2
R3
Product
Time (h)
Yield (%)b
6
n
a
R3-NC
n
I
1
2
H
H
Cyclohexyl
Cyclohexyl
Cyclohexyl
Cyclohexyl
Cyclohexyl
Cyclohexyl
Cyclohexyl
Cyclohexyl
Cyclohexyl
Tert-butyl
Tert-butyl
Tert-butyl
Tert-butyl
Tert-butyl
Tert-butyl
Tert-butyl
Tert-butyl
Tert-butyl
5a
5b
5c
5d
5e
5f
4
3
4
4
3
4
5
6
6
4
4
5
5
4
4
5
5
5
97
98
94
95
96
93
93
92
91
95
97
94
93
95
92
91
90
89
u
3
R3
C
R2
H
4-Cl
2-Me
H
O
O
N
H
N
3
H
R2
H2N
4
4-NO2
4-Br
4-Me
4-Cl
2-Cl
4-NO2
H
O
O
O
4
5
H
H
6
H
R1
O
N
7
4-Br
4-Me
4-OMe
H
5g
5h
5i
8
7
O
R1
R3
8
O
9
o
n
R1
10
11
12
13
14
15
16
17
18
5j
-Me2CO
a
n
H
4-Cl
2-Me
H
5k
5l
I
O
u
C
R2
R3
H
H
N
R2
O
4-NO2
4-Br
4-Me
4-Cl
2-Cl
4-NO2
5m
5n
5o
5p
5q
5r
NH2
N
O
R3
4
H
O
O
H
4-Br
4-Me
4-OMe
N
NH
HN
H
O
R2
R2
a
R1
Reaction and conditions: aldehyde/Meldrum’s acid/isocyanide and
amine = 2:2:2:4, 2 mol% nano CuI, EtOH; rt.
5
b
Isolated yield.
Scheme 2. Possible mechanism for the formation of tricarboxamides.

198
A. Ziarati et al. / Chinese Chemical Letters 24 (2013) 195–198
[13] J.L. Wang, D. Liu, Z.J. Zheng, et al., Structure-based discovery of an organic
compound that binds Bcl-2 protein and induces apoptosis of tumor cells, Proc.
Natl. Acad. Sci. U. S. A. 97 (2000) 7124–7129.
[14] K. Strom, J. Sjogren, A. Broberg, J. Schnurer, Lactobacillus plantarum MiLAB 393
produces the antifungal cyclic dipeptides cyclo(L-Phe-L-Pro) and cyclo(L-Phe-
trans-4-OH-L-Pro) and 3-phenyllactic acid, Appl. Environ. Microbiol. 68 (2002)
4322–4327.
it was reasonable to assume that the reaction of iminolactone with
amine leaded to produce vinylogous carbonate 8. Subsequently, in
the presence of CuI, 8 reacted with another molecule of amine to
afford product 5 after losing acetone.
[15] X. Tang, L. Fan, H. Yu, Y. Liao, D. Yang, Facile synthesis of dipeptidomimetics of p-
aminobenzoic acid and their antidiabetic activity, Chin. J. Org. Chem. 29 (2009)
595–600.
4. Conclusion
In conclusion, we have demonstrated an efficient, clean, and
one-pot procedure for the synthesis of tricarboxamides via five-
component coupling of Meldrum’s acid, isocyanides with aromatic
aldehydes and amines over the high surface area of nano CuI as
catalyst at room temperature. Wide range of products, mild
reaction conditions, excellent yields of the products, reduced time
of reaction, and a recyclable catalyst are advantages of this
procedure over the previous reported ones.
[16] A.I. Faden, V.A. Movsesyan, S.M. Knoblach, F. Ahmed, I. Cernak, Neuroprotective
effects of novel small peptides in vitro and after brain injury, Neuropharmacology
49 (2005) 410–424.
[17] C.B. Cui, H. Kakeya, H. Osada, Novel mammalian cell cycle inhibitors, cyclotro-
prostatins A–D, produced by Aspergillus fumigatus, which inhibit mammalian cell
cycle at G2/M phase, Tetrahedron 53 (1997) 59–72.
[18] M.B. Teimouri, P. Akbari-Moghaddam, G. Golbaghi, Pseudo-five-component re-
action between 3-formylchromones, Meldrum’s acid, isocyanides and primary
arylamines: diversity-oriented synthesis of novel chromone-containing peptido-
mimetics, ACS Comb. Sci. 13 (2011) 659–666.
[19] A. Shaabani, M.B. Teimouri, A. Bazgir, H.R. Bijanzadeh, Introducing a novel class of
four-component reactions, Mol. Divers. 6 (2003) 199–206.
[20] M.B. Teimouri, P. Akbari-Moghaddam, An efficient one-pot method for the
synthesis of novel ferroceneetriamide conjugates via pseudo five-component
reaction, Tetrahedron 67 (2011) 5928–5934.
[21] A. Shaabani, M. Seyyedhamzeh, A. Maleki, M. Behnam, F. Rezazadeh, Synthesis of
fully substituted pyrazolo[3,4-b]pyridine-5-carboxamide derivatives via a one-
pot four-component reaction, Tetrahedron Lett. 50 (2009) 2911–2913.
[22] F. Cagide, J. Reis, A. Gaspar, F. Borges, Accelerating lead optimization of chromone
carboxamide scaffold throughout microwave-assisted organic synthesis, Tetra-
hedron Lett. 52 (2011) 6446–6449.
Acknowledgment
The authors are grateful to University of Kashan for supporting
this work by Grant No. 159196/XII.
Appendix A. Supplementary data
[23] N. Koukabi, E. Kolvari, A. Khazaei, et al., Hantzsch reaction on free nano-Fe2O3
catalyst: excellent reactivity combined with facile catalyst recovery and recycla-
bility, Chem. Commun. 47 (2011) 9230–9232.
[24] S. Shylesh, V. Schunemann, W.R. Thiel, Magnetically separable nanocatalysts:
bridges between homogeneous and heterogeneous catalysis, Angew. Chem. Int.
Ed. 49 (2010) 3428–3459.
[25] M.Z. Kassaee, R. Mohammadi, H. Masrouri, et al., Nano TiO2 as a heterogeneous
catalyst in an efficient one-pot three-component Mannich synthesis of b-ami-
nocarbonyls, Chin. Chem. Lett. 22 (2011) 1203–1206.
[26] A. Teimouri, A. Najafi Chermahini, One-pot green synthesis of pyrrole derivatives
catalyzed by nano sulfated zirconia as a solid acid catalyst, Chin. J. Chem. 30
(2012) 372–376.
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.cclet.2013.01.049.
References
[1] A. Basso, L. Banfi, R. Riva, G. Guanti, A novel highly selective chiral auxiliary for the
asymmetric synthesis of L- and D-a-amino acid derivatives via a multicomponent
Ugi ueaction, J. Org. Chem. 70 (2005) 575–579.
´
[2] D.J. Ramon, M. Yus, Asymmetric multicomponent reactions (AMCRs): the new
frontier, Angew. Chem. Int. Ed. 44 (2005) 1602–1634.
[27] M. Nikpassand, L. Zare, T. Shafaati, S. Shariati, Regioselective synthesis of fused
azo-linked pyrazolo[4,3-e]pyridines using nano-Fe3O4, Chin. J. Chem. 30 (2012)
604–608.
[28] J. Safaei-Ghomi, A. Ziarati, R. Teymuri, CuI nanoparticles as new, efficient and
reusable catalyst for the one-pot synthesis of 1,4-dihydropyridines, Bull. Korean
Chem. Soc. 33 (2012) 2679–2682.
[29] H.J. Xu, Y.F. Liang, X.F. Zhou, Y.S. Feng, Efficient recyclable CuI-nanoparticle-
catalyzed S-arylation of thiols with aryl halides on water under mild conditions,
Org. Biomol. Chem. 10 (2012) 2562–2568.
[30] J. Safaei-Ghomi, A. Ziarati, S. Zahedi, Ferric chloride supported on nano silica as a
reusable heterogeneous catalyst for the one-pot synthesis of 1,4-dihydropyri-
dines under mild conditions, J. Chem. Sci. 124 (2012) 933–939.
[31] J. Safaei-Ghomi, A. Ziarati, An efficient FeCl3/SiO2 NPs as a reusable heterogeneous
catalyzed five-component reactions of tetrahydropyridines under mild condi-
tions, J. Iran Chem. Soc. 10 (2013) 135–139.
[3] V. Nair, C. Rajesh, A.U. Vinod, et al., Strategies for heterocyclic construction via
novel multicomponent reactions based on isocyanides and nucleophilic carbenes,
Acc. Chem. Res. 36 (2003) 899–907.
[4] W.G. Yi, Z.Y. Jia, N.B. Li, et al., Zirconocene bis(perfluorooctanesulfonate)s-cata-
lyzed the reaction of indoles and carbonyl compounds, Chin. J. Org. Chem. 32
(2012) 2390–2393.
[5] C. Ma, Y. Yang, Thiazolium-mediated multicomponent reactions: a facile synthe-
sis of 3-aminofuran derivatives, Org. Lett. 7 (2005) 1343–1345.
[6] Y. Cheng, O. Meth-Cohn, Heterocycles derived from heteroatom-substituted
carbenes, Chem. Rev. 104 (2004) 2507–2530.
[7] H. Anaraki-Ardakani, M. Noei, A. Tabarzad, Facile synthesis of N-(arylsulfonyl)-4-
ethoxy-5-oxo-2,5-dihydro-1H-pyrolle-2,3-dicarboxylates by one-pot three-com-
ponent reaction, Chin. Chem. Lett. 23 (2012) 45–48.
[8] A. Domling, Recent developments in isocyanide based multicomponent reactions
in applied chemistry, Chem. Rev. 106 (2006) 17–89.
[9] A. Domling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int.
Ed. 39 (2000) 3169–3210.
[32] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient
and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23
(2012) 1225–1229.
[10] A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Recent progress of isocyanide-
based multicomponent reactions in Iran, Mol. Divers. 15 (2011) 41–68.
[11] S. Sadjadi, M.M. Heravi, Recent application of isocyanides in synthesis of hetero-
cycles, Tetrahedron 67 (2011) 2707–2752.
[12] A.V. Ivachtchenko, Y.A. Ivanenkov, V.M. Kysil, et al., Multicomponent reactions of
isocyanides in the synthesis of heterocycles, Russ. Chem. Rev. (Engl. Transl.) 79
(2010) 787–817.
[33] V. Nair, R.S. Menon, A.U. Vinod, S.A. Viji, A facile three-component reaction
involving [1+4] cycloaddition leading to furan annulated heterocycles, Tetrahe-
dron Lett. 43 (2002) 2293–2295.
[34] A. Shaabani, S. Ajabi, F. Farrokhzad, H.R. Bijanzadeh, [1+4] Cycloaddition of
isocyanides with 2-acetyl-1,4-benzoquinone; a conveient synthesis of isobenzo-
furan-4,7-quinones, J. Chem. Res. (1999) 582–583.
[35] B.C. Chen, Meldrum’s acid in organic synthesis, Heterocycles 32 (1991) 529–597.