One-pot Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Polyphosphoric Acid Supported on Silica-coated NiFe2O4 Nanoparticles

Full text of DOI:10.1080/00304948.2016.1127098

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
ISSN: 0030-4948 (Print) 1945-5453 (Online) Journal homepage: http://www.tandfonline.com/loi/uopp20
One-pot Synthesis of 1-Amidoalkyl-2-naphthols
Catalyzed by Polyphosphoric Acid Supported on
Silica-coated NiFe2O4 Nanoparticles
Behrooz Maleki, Elham Sheikh, Esmail Rezaei Seresht, Hossein Eshghi,
Samaneh Sedigh Ashrafi, Amir Khojastehnezhad & Hojat Veisi
To cite this article: Behrooz Maleki, Elham Sheikh, Esmail Rezaei Seresht, Hossein Eshghi,
Samaneh Sedigh Ashrafi, Amir Khojastehnezhad & Hojat Veisi (2016) One-pot Synthesis of
1-Amidoalkyl-2-naphthols Catalyzed by Polyphosphoric Acid Supported on Silica-coated
NiFe2O4 Nanoparticles, Organic Preparations and Procedures International, 48:1, 37-44, DOI:
10.1080/00304948.2016.1127098
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Date: 30 January 2016, At: 03:29

Organic Preparations and Procedures International, 48:37–44, 2016
Copyright Ó Taylor & Francis Group, LLC
ISSN: 0030-4948 print / 1945-5453 online
DOI: 10.1080/00304948.2016.1127098
One-pot Synthesis of 1-Amidoalkyl-2-naphthols
Catalyzed by Polyphosphoric Acid Supported on
Silica-coated NiFe2O4 Nanoparticles
Behrooz Maleki,1 Elham Sheikh,1 Esmail Rezaei Seresht,1
Hossein Eshghi,2 Samaneh Sedigh Ashrafi,1
Amir Khojastehnezhad,3 and Hojat Veisi4
1Department of Chemistry, Hakim Sabzevari University, Sabzevar, 96179-
76487, Iran
2Department of Chemistry, Faculty of Sciences, Ferdowsi University of
Mashhad, Mashhad, Iran
3Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University,
Mashhad, Iran
4Department of Chemistry, Payame Noor University (PNU), 19395-4697
Tehran, Iran
Magnetic nanoparticles (MNPs) have proven to be a valuable asset in organic chemistry.
There have been several studies carried out on their biological and technological applica-
tions such as drug delivery,1,2 magnetic resonance imaging (MRI),3 bio-separation,4,5
bimolecular sensors6,7 and magneto-thermal therapy.8,9 Recent reports show that the use
of magnetic nanoparticles can facilitate the isolation and recycling of expensive catalysts
from the reaction mixtures.10,11
1-Amidoalkyl-2-naphthols (4) have attracted considerable attention due to their pres-
ence as a part of some biologically important natural products and as crucial building
blocks for a variety of pharmaceuticals, and potent drugs, including a number of nucleo-
side anti-biotics and HIV protease inhibitors.12 Furthermore, hydrolysis of these com-
pounds lead to 1-aminoalkyl-2-naphthols13 which are useful as hypotensive and
bradycardiac agents14 and may also be converted to 1,3-oxazine derivatives;15 1,3-oxa-
zines display various biological action including anti-biotic,16 anti-tumor,17 analgesic,18
anti-convulsant,19 anti-psychotic,20 anti-malarial,21 anti-anginal,22 anti-hypertensive,23
and anti-rheumatic24 activities. 1-Amidoalkyl-2-naphthols have been obtained via the
multi-component condensation of 2-naphthol, aldehydes, and acetonitrile or amides in
the presence of acid catalysts such as copper perchlorate hexahydrate [Cu
(ClO4)2.6H2O],25 tin(II) chloride dihydrate [SnCl2.2H2O],26 ferric bisulfate [Fe
(HSO4)3],27 strontium(II) triflate [Sr(OTf)2],28 molecular iodine (I2),29 aluminum tris
(dihydrogenphosphate)
[Al(H2PO4)3],30
silicotungstic
acid
(H4SiW12O40),31
N-(4-sulfonic acid) butyltriethylammonium bisulfate ([TEBSA][HSO4]),32 zinc
Received April 29, 2015; in final form September 1, 2015.
Address correspondence to Behrooz Maleki, Department of Chemistry, Hakim Sabzevari Uni-
versity, Sabzevar, 96179-76487, Iran. E-mail: malekibehrooz@gmail.com
37

38
Maleki et al.
benzenesulfonate (ZBS),33 montmorillonite K10,34 molten 4-(1-imidazolium)butanesul-
fonate,35 perchloric acid supported on alumina (Al2O3-HClO4),36 silica gel–supported
polyphosphoric acid (PPA-SiO2),37 alum [KAl(SO4)2.12H2O],38 phosphorus pentoxide
(P2O5),39 potassium dodecatungstocobaltate trihydrate (K5CoW12O40.3H2O),40 sulfamic
acid/ultrasound,41 silica-supported perchloric acid (HClO4-SiO2),42 nanosilica phosphoric
acid (H3PO4-SiO2),43 3-methyl-1-sulfonic acid imidazolium chloride [Msim][Cl],44 silica
sulfuric acid (SSA),45 nano-S (S8-NP),46 NiFe2O4@ MCM-41-SO3H,47 zirconyl(IV)
chloride (ZrOCl2),48 oxalic acid,49 magnesium perchlorate [Mg(ClO4)2],50 dodecylphos-
phonic acid (DPA),51 wet cyanuric chloride,52 cerium(IV) sulfate [Ce(SO4)2],53 silica-
supported sodium bisulfate (NaHSO4-SiO2),54 Fe3O4@SiO2-Imid-H3PMo12O40,55 nano-
Fe3O4 modified carbon nanotubes using microwave irradiation,56 MCM-41-N-propylsul-
famic acid,57 and polyphosphate ester (PPE).58 However, some of these catalysts suffer
from drawbacks such as prolonged reaction times, use of toxic and corrosive solvent,
non-re-usable and/or expensive catalysts, unsatisfactory yields, and the need to use micro-
wave or ultrasonic irradiation in some cases. Therefore, the development of new proce-
dures, utilizing eco-friendly and effective catalysts that can be easily recycled at the end
of the reaction, would be a worthy goal. To the best of our knowledge, there is no report
on the use of polyphosphoric acid supported on silica-coated NiFe2O4 nanoparticle
(NiFe2O4@SiO2–PPA) for the preparation of 1-amidoalkyl-2-naphthols. In continuation
of our previous studies on the development of green and new catalysts,59-74 we describe
here a simple, mild and efficient procedure for the one-pot three-component synthesis of
1-amidoalkyl-2-naphthols from 2-naphthol, various aldehydes, and amides (benzamide,
acetamide or urea) using NiFe2O4@SiO2–PPA as the catalyst under solvent-free condi-
tions (Scheme 1).
Scheme 1
To determine the optimum conditions, the reaction of benzaldehyde (0.106 g,
1 mmol), 2-naphthol (0.144 g, 1 mmol), and benzamide (0.145 g, 1.2 mmol) in the pres-
68
ence of NiFe2O4@SiO2–PPA (0.04 g), prepared according to the literature procedure,
was performed under thermal solvent-free conditions at different temperatures in an oil
bath (Table 1, Entries 1–3). Table 1 shows that the shortest time and best yields were
achieved at 120ꢀC (Entry 1) and the optimal amount NiFe2O4@SiO2–PPA (0.04 g,
Entries 4 and 5) to catalyze the reaction smoothly. Further increase the amount of
NiFe2O4@SiO2–PPA did not lead to appreciable increases in yields; no conversion to
product was obtained in the absence of catalyst even after 1 h (Entry 6).
The use of these optimized conditions allowed us to explore the scope and efficiency
of this procedure for the synthesis of a wide variety of substituted corresponding 1-ami-
doalkyl-2-naphthol derivatives. The results summarized in Table 2 shows that the reac-
tion works well with a variety of aldehydes including those bearing electron-withdrawing
and electron-donating groups. On the other hand, only traces of corresponding products
were produced from the reaction with a,b-unsaturated and aliphatic aldehydes such as

One-pot Synthesis of 1-Amidoalkyl-2-naphthols
39
Table 1
Optimization of the Amount of NiFe2O4@SiO2–PPA and Temperature in the Synthesis of
N-[phenyl-(2-hydroxynapthalen-1-yl)-methyl]benzamide (4a)
Amount of NiFe2O4
@SiO2–PPA (g)
Temperature
(ꢀC)
Time
(min)
Yield
(%)
Entry
1
2
3
4
5
6
0.04
0.04
0.04
0.03
0.05
120
110
100
120
120
120
5
5
92
79
78
83
85
10
5
4
60
a
b
–
–
aIn the absence of NiFe2O4@SiO2–PPA.
bNo reaction
Table 2
One-pot Synthesis of 1-Amidoalkyl-2-naphthol in the Presence of NiFe2O4@SiO2–PPA
under Solvent-Free Conditions
mp (ꢀC)
Product (4)
Ar
R1 Time (min) Yield (%)
Found
Lit.
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
4p
4q
4r
C6H5
Ph
Ph
Ph
Ph
Ph
Ph
Ph
5
7
92
91
82
96
93
94
90
90
86
92
85
95
80
88
80
90
90
95
236–238 234–23644
188–190 187–18844
284–285 284–28539
228–229 228–22939
210–212 214–21644
214–216 216–21752
225–227 228–23027
204–206 208–20939
239–240 241–24352
245–247 247–24942
238–240 235–23742
230–232 228–23052
213–215 213–21536
224–227 223–22539
220–221 220–22242
169–171 172–17452
174–176 170–17252
192–194 189–19052
4-ClC6H4
2-ClC6H4
4-NO2C6H4
3-NO2C6H4
4-CH3C6H4
4-BrC6H4
8
7
7
10
8
4-CH3OC6H4 Ph
C6H5 CH3
10
7
4-NO2C6H4 CH3
3-NO2C6H4 CH3
7
7
4-BrC6H4
2-ClC6H4
4-ClC6H4
CH3
CH3
CH3
10
10
10
15
7
4-CH3C6H4 CH3
C6H5
4-ClC6H4
NH2
NH2
10
7
3-NO2C6H4 NH2

40
Maleki et al.
Table 3
Comparison of Methods for the Synthesis of 1-Amidoalkyl-2-naphthols
Entry
Conditions
Time (min) Yield (%)
Present work
Cu(ClO4)2.6H2O/ultrasound/rt25
5
92
89
96
92
91
95
86
45
18
15
15
50
6
SnCl2.2H2O/solvent-free/80ꢀC26
Zinc benzenesulfonate (ZBS)/solvent-free/80ꢀC33
KAl(SO4)2.12H2O/solvent-free/85ꢀC38
Nano silica phosphoric acid/solvent-free/80ꢀC43
3-Methyl-1-sulfonic acid imidazolium
chloride [Msim][Cl]/solvent-free/120ꢀC44
NiFe2O4@MCM-41-SO3H/solvent-free/100ꢀC47
Fe3O4@SiO2-Imid-H3PMo12O40/solvent-free/
microwave irradiation (360 w)55
4a
240
8
92
93
Nano-Fe3O4 modified carbon nanotubes/solvent-free/
microwave irradiation56
5
90
Polyphosphate ester (PPE)/solvent-free/80ꢀC58
Present work
10
6
90
93
90
92
93
91
80
86
Cu(ClO4)2.6H2O/ultrasound/rt25
SnCl2.2H2O/solvent-free/80ꢀC26
KAl(SO4)2.12H2O/solvent-free/85ꢀC38
Nano silica phosphoric acid/solvent-free/80ꢀC43
NiFe2O4@MCM-41-SO3H/solvent-free/100ꢀC47
Fe3O4@SiO2-Imid-H3PMo12O40/solvent-free/
microwave irradiation (360 w)55
30
120
15
45
300
15
4f
Present work
Fe(HSO4)3/solvent-free/85ꢀC27
5
95
89
90
91
92
87
45
60
10
10
12
Cu(ClO4)2.6H2O/ ultrasound / rt25
KAl(SO4)2.12H2O/solvent-free/85ꢀC38
Wet cyanuric chloride/100ꢀC52
4l
Fe3O4@SiO2-Imid-H3PMo12O40/solvent-free/
microwave irradiation (360 w)55
MCM-41-N-propylsulfamic acid/solvent-free/130ꢀC57
190
87
crotonaldehyde, cinnamaldehyde, formaldehyde, acetaldehyde, butyraldehyde and
isobutyraldehyde.
In order to examine the recyclability of NiFe2O4@SiO2-PPA, the major portion of
the catalyst was recovered by placing a magnet (1.4 T field strength) on the side of the
reaction vessel75 and decantation of the clear solution containing the product. After wash-
ing with acetone and drying at 100ꢀC for 2h, the recovered catalyst was re-used six times
in the reaction of 2-naphthol and benzaldehyde with benzamide, to afford 92%, 90%,
89%, 88%, 88 and 87% yields, respectively.
We also compared our results using NiFe2O4@SiO2-PPA with data reported in the
literature. Table 3 clearly demonstrates NiFe2O4@SiO2-PPA to be a simple and effective
catalyst with respect to reaction times, simplicity of procedure, facile work-up and yields
comparable to those obtained using some of the other catalysts.

One-pot Synthesis of 1-Amidoalkyl-2-naphthols
41
Although the yields utilizing NiFe2O4@SiO2-PPA are not better than some of those
using other methods, comparison with homogeneous polyphosphoric acid (PPA) shows
its effective-ness. Polyphosphoric acid (PPA) suffers from drawbacks such as a) non-
reusability and difficult separation, b) necessity to neutralize the reaction mixtures prior
to product isolation c) low stability, d) higher cost, e) higher toxicity and f) sensitivity to
moisture and air. NiFe2O4@SiO2-PPA is easily separated using a magnet68 and may be
re-used without loss of activity. It is very stable, highly efficient due to its greater surface
area and inexpensive because of the re-usability. These properties make NiFe2O4@SiO2-
PPA attractive as novel magnetically separable catalyst for the synthesis of aminoalkyl-2-
naphthols.
Experimental Section
Chemicals were obtained from Merck and Fluka. IR spectra were recorded on a Shimadzu
435-U-04 spectrophotometer (KBr pellets). 1H NMR spectra were obtained using Jeol FT
NMR 90 MHz and spectrometer in CDCl3 using TMS as an internal reference. Melting
points were determined in open capillary tubes in a Stuart BI Branstead Electrothermal
Cat No:IA9200 apparatus and uncorrected. A neodymium magnet (also known as NdFeB,
NIB or Neo magnet) with field strength of 1.4T was purchased from Ningbo Tongchuang
Strong Magnet Material Co., Ltd (China).
General Procedure for the Synthesis of 1-Amidoalkyl-2-naphthols (4a-r)
To mixture of aldehyde (1 mmol), 2-naphthol (0.144 g, 1 mmol), the amide (benzamide
or acetamide or urea) [0.145 g or 0.072 g or 0.0708 g, 1.2 mmol] was added NiFe2O4@-
SiO2-PPA (0.04 g) and the mixture was heated on an oil bath at 120ꢀC for the time show
in Table 2. After completion of the reaction (monitored by TLC, n-hexane-ethyl acetate,
4:1), the reaction mixture was diluted with hot EtOH (96%, 2 ml) and partitioned as fol-
lows. The nanomagnetic catalyst was separated from the reaction mixture by employing
an external magnet [the catalyst that was suspended in the ethanolic solution could be
made to adhere to the side of reaction vessel with the aid of the external magnet (1.4 T
field strength)] and the thus separated catalyst was then loosened, washed with acetone
and dried at 100ꢀC for 2 h and re-used]. The clear solution containing the crude product
that had been decanted to another vessel was poured onto crushed ice. The solid product
which precipitated, was collected and recrystallized from 96% ethanol (2 ml) to afford
the 1-amidoalkyl-2-naphthols.
Larger Scale Preparation of 4a
To mixture of benzaldehyde (5.3 g, 50 mmol), 2-naphthol (7.2 g, 50 mmol), and benza-
mide (7.26 g, 60 mmol) was added NiFe2O4@SiO2–PPA (2 g) and the mixture was
heated on an oil bath at 120ꢀC for the time 10 min. After completion of the reaction
(monitored by TLC, n-hexane:ethyl acetate, 4:1) the reaction mixture was diluted with
hot EtOH (96%, 5 ml) and the nanomagnetic catalyst was separated from the reaction
mixture as described above and the product isolated as described above and recrystallized
from 96% ethanol (15 ml) to afford 15.18 g (86%) of N-[phenyl-(2-hydroxynapthalen-1-
yl)-methyl]benzamide (4a).

42
Maleki et al.
Acknowledgements
The authors thank the Research Council of Hakim Sabzevari University for partial sup-
port of this work.
References
1. A. K. Gupta and A. S. Curtis, J. Mater, J. Mater. Sci. Mater. Med., 15, 493 (2004).
2. T. Neuberger, B. Schopf, H. Hofmann, M. Hofmann and B. V. Rechenberg, J. Magn. Magn.
Mater., 293, 483 (2005).
3. Q. A. Pankhurst, J. Connolly, S. K. Jones and J. Dobson, J. Phys. D: Appl. Phys., 36, 167
(2003).
4. D. Wang, J. He, N. Rosenzweig and Z. Rosenzweig, Nano Lett., 4, 409 (2004).
5. C. Xu, K. Xu, H. Gu, R. Zheng, H. Liu, X. Zhang, Z. Guo and B. Xu, J. Am. Chem. Soc., 126,
9938 (2004).
6. J. M. Perez, F. J. Simeone, Y. Saeki, L. Josephson and R. Weissleder, J. Am. Chem. Soc., 125,
10192 (2003).
7. D. L. Graham, H. A. Ferreira and P. P. Freitas, Trends Biotechnol., 22, 455 (2004).
8. R. Hiergeist, W. Andra, N. Buske, R. Hergt, I. Hilger, U. Richter and W. Kaiser, J. Magn.
Magn. Mater., 201, 420 (1999).
9. A. Jordan, R. Scholz, P. Wust, H. Fahling and R. Felix, J. Magn. Magn. Mater., 201, 413 (1999).
10. M. Shokouhimehr, Y. Piao, J. Kim, Y. Jang and T. Hyeon, Angew. Chem., Int. Ed., 37, 7169
(2007).
11. R. Tayebee, M. M. Amini, N. Abdollahi, A. Aliakbari, S. Rabiei and H. Ramshini, Appl. Catal.
A: Gen., 468, 75 (2013).
12. S. Knapp, Chem. Rev., 95, 1859 (1995).
13. A. Y. Shen, C. T. Tsai and C. L. Chen, Eur. J. Med. Chem., 34, 877 (1999).
14. T. Dingermann, D. Steinhilber and G. Folkers, Molecular Biology in Medicinal Chemistry,
Wiley-VCH, Weinheim, (2003).
15. M. Damodiran, N. P. Selvam and P. T. Perumal, Tetrahedron Lett., 50, 5474 (2009).
16. Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose and S. Shirato, J. Antibiotic., 2,
44 (1972).
17. S. Remillard, L. I. Rebhun, G. A. Howie and S. M. Kupchan, Science 189, 1002 (1975).
18. G. Y. Lesher and A. R. Surrey, J. Am. Chem. Soc., 77, 636 (1955).
19. H. S. Mosher, M. B. Frankel and M. Gregory, J. Am. Chem. Soc., 75, 5326 (1953).
20. J. L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot and M. J. Millan, Bioorg. Med.
Chem. Lett., 7, 881 (1997).
21. H. Ren, S. Grady, D. Gamenara, H. Heinzen, P. Moyna, S. L. Croft, H. Kendrick, V. Yardley
and G. Moyna, Bioorg. Med. Chem. Lett., 11, 1851 (2001).
ꢀ
22. F. Benedini, G. Bertolini, R. Cereda, G. Dona, G. Gromo, S. Levi, J. Mizrahi and A. Sala, J.
Med. Chem., 38, 130 (1995).

One-pot Synthesis of 1-Amidoalkyl-2-naphthols
43
23. R. D. Clark, J. M. Caroon, A. F. Kluge, D. B. Repke, A. P. Roszkowski, A. M. Strosberg, S.
Baker, S. M. Bitter and M. D. Okada, J. Med. Chem., 26, 657 (1983).
24. H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T.
Akimoto, Y. Takeda, K. Yano and T. Kuroki, J. Med. Chem., 40, 105 (1997).
25. S. Puri, B. Kaur, A. Parmar and H. Kumar, Org. Prep. Proced. Int., 44, 91 (2012).
26. M. Wang, Z. G. Song and Y. Liang, Org. Prep. Proced. Int., 43, 484 (2011).
27. H. R. Shaterian, H. Yarahmadi and M. Ghashang, Bioorg. Med. Chem. Lett., 18, 788 (2008).
28. W. K. Su, W. Y. Tang and J. J. Li, J. Chem. Res., 123 (2008).
29. B. Das, K. Laxminarayana, B. Ravikanth and B. R. Rao, J. Mol. Catal. A: Chem., 261, 180
(2007).
30. H. R. Shaterian, A. Amirzadeh, F. Khorami and M. Ghashang, Synth. Commun., 38, 2983
(2008).
31. A. R. Supale and G. S. Gokavi, J. Chem. Sci., 122, 189 (2010).
32. A. R. Hajipour, Y. Ghayeb, N. Sheikhan and A. E. Ruoho, Tetrahedron Lett., 50, 5649 (2009).
33. M. Wang, Z. G. Song and Y. Liang, Synth. Commun., 42, 582 (2012).
34. S. Kantevari, S. V. N. Vuppalapati and L. Nagarapu, Catal. Commun., 8, 1857 (2007).
35. D. Kundu, A. Majee and A. Hajra, Catal. Commun., 11, 1157 (2010).
36. H. R. Shaterian, F. Khorami, A. Amirzadeh and M. Ghashang, Chin. J. Chem., 27, 815 (2009).
37. H. R. Shaterian, A. Hosseinian and M. Ghashang, Synth. Commun., 38, 3375 (2008).
38. H. A. Oskooie, M. M. Heravi, N. Karimi, A. Amouchi and G. Kohansal, Synth. Commun., 42,
109 (2012).
39. G. C. Nandi, S. Samai, R. Kumar and M. S. Singh, Tetrahedron Lett., 50, 7220 (2009).
40. L. Nagarapu, M. Baseeruddin, S. Apuri and S. Kantevari, Catal. Commun., 8, 1729 (2007).
41. S. B. Patil, P. R. Singh, M. P. Surpur and S. D. Samant, Ultrason. Sonochem., 14, 515 (2007).
42. H. R. Shaterian, H. Yarahmadi and M. Ghashang, Tetrahedron 64, 1263 (2008).
43. A. Bamoniri, B. F. Mirjalili and S. Nazemian, J. Iran. Chem. Soc., 11, 653 (2014).
44. M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare and V. Khakyzadeh, Appl. Catal. A:
Gen., 400, 70 (2011).
45. G. Srihari, M. Nagaraju and M. M. Murthy, Helv. Chim. Acta 90, 1497 (2007).
46. V. K. Das, M. Borah and A. J. Thakur, J. Org. Chem., 78, 3361 (2013).
47. Z. Cai, C. Shu and Y. Peng, Monatsh Chem., 145, 1681 (2014).
48. R. R. Nagawade and D. B. Shinde, Acta Chim. Slov., 54, 642 (2007).
49. S. A. M. K. Ansari, N. S. Jiaprakash, D. K. S. Nagnnath, W. Pravin and D. B. Shinde, Indian J.
Chem. Technol., 17, 71 (2010).
50. M. A. Amrollahi, F. Mirjalili and H. Emtiazi, J. Chem. Sci., 125, 561 (2013).
51. M. Zandi and A. R. Sardarian C. R. Chim., 15, 365 (2012).
52. G. H. Mahdavinia and M. A. Bigdeli, Chin. Chem. Lett., 20, 383 (2009).

44
Maleki et al.
53. N. P. Selvam and P. T. Perumal, Tetrahedron Lett., 47, 7481 (2006).
54. H. R. Shaterian, A. Hosseinian and M. Ghashang, Tetrahedron Lett., 49, 5804 (2008).
55. M. Esmaeilpour, J. Javidi and M. Zandi, Mater. Res. Bull., 55, 78 (2014).
56. J. Safari and Z. Zarnegar, J. Indus. Engin. Chem., 20, 2292 (2014).
57. M. Hajjami, F. Ghorbani and F. Bakhti, Appl. Catal. A: Gen., 470, 303 (2014).
58. H. Moghanian and S. Ebrahimi, J. Saudi Chem. Soc., 18, 165 (2014).
59. B. Maleki and S. Sedigh Ashrafi, RSC Adv., 4, 42873 (2014).
60. B. Maleki, S. Sedigh Ashrafi and R. Tayebee, RSC Adv., 4, 41521 (2014).
61. H. Veisi, B. Maleki, F. Hosseini Eshbala, H. Veisi, R. Masti, S. Sedigh Ashrafi and M.
Baghayeri, RSC Adv., 4, 30683 (2014).
62. B. Maleki, S. Hemmati, A. Sedrpoushan, S. Sedigh Ashrafi and H. Veisi, RSC Adv., 4, 40505
(2014).
63. H. Veisi, B. Maleki, M. Hamelian andS. Sedigh Ashrafi, RSC Adv., 5, 6365 (2015).
64. B. Maleki and F. Taimazi, Org. Prep. Proced. Int., 46, 252 (2014).
65. B. Maleki, E. Rezaee-Seresht and Z. Ebrahimi, Org. Prep. Proced. Int., 47, 149 (2015).
66. B. Maleki, Org. Prep. Proced. Int., 47, 173 (2015).
67. B. Maleki, S. Barat Nam Chalaki, S. Sedigh Ashrafi, E. R.ezaee Seresht, F. Moeinpour, A. Kho-
jastehnezhad and R. Tayebee, Appl. Organomet. Chem., 29, 290 (2015).
68. A. Khojastehnezhad, M. Rahimizadeh, F. Moeinpour, H. Eshghi and M. Bakavoli, C. R. Chim.,
17, 459 (2014).
69. H. Veisi, A. Naeimi, B. Maleki, S. Sedigh Ashrafi and A. Sedrpoushan, Org. Prep. Proced. Int.,
47, 309 (2015).
70. B. Maleki, F. Mohammadi Zonoz and H. A. Akhlaghi, Org. Prep. Proced. Int., 47, 361 (2015).
71. B. Maleki and S. Sheikh, Org. Prep. Proced. Int., 47, 368 (2015).
72. B. Maleki and S. Sheikh, RSC Adv., 5, 42997 (2015).
73. B. Maleki, G. Esmailian Kahoo and R. Tayebee, Org. Prep. Proced. Int., 47, 461 (2015).
74. B. Maleki, M. Raei, E. Akbarzadeh, H. Ghasemnejad-Bosra, A. R. Sedrpoushan, S. Sedigh Ashrafi, and
M. Nabi Dehdashti, Org. Prep. Proced. Int., 48, 62 (2016).
75. D. Wang and D. Astruc, Chem. Rev., 114, 6949 (2014).