Greener Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-ones in a Deep Eutectic Solvent

Full text of DOI:10.1080/00304948.2020.1799672

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
ISSN: (Print) (Online) Journal homepage: https://www.tandfonline.com/loi/uopp20
Greener Synthesis of 3,4-Disubstituted
Isoxazole-5(4H)-ones in a Deep Eutectic Solvent
Hengameh Atharifar , Ali Keivanloo & Behrooz Maleki
To cite this article: Hengameh Atharifar , Ali Keivanloo & Behrooz Maleki (2020): Greener
Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-ones in a Deep Eutectic Solvent, Organic
Preparations and Procedures International, DOI: 10.1080/00304948.2020.1799672
To link to this article: https://doi.org/10.1080/00304948.2020.1799672
Published online: 26 Oct 2020.
Submit your article to this journal
View related articles
View Crossmark data
Full Terms & Conditions of access and use can be found at
https://www.tandfonline.com/action/journalInformation?journalCode=uopp20

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
https://doi.org/10.1080/00304948.2020.1799672
EXPERIMENTAL PAPER
Greener Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-ones
in a Deep Eutectic Solvent
a
a
b
Hengameh Atharifar , Ali Keivanloo
, and Behrooz Maleki
a
b
Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran; Department of Chemistry,
Hakim Sabzevari University, Sabzevar, Iran
ARTICLE HISTORY Received 6 March 2020; Accepted 11 June 2020
Developing a cost effective and environmentally benign solvent system is of the utmost
importance in the chemical industry. One current proposal is the replacement of con-
ventional hazardous volatile organic solvents by nonvolatile alternatives so that they do
1
not emit toxic or flammable vapors over a wide range of temperatures. During the past
2
few years, some green solvents have been used. These include water, supercritical flu-
3
4–5
6
7
ids, perfluorinated solvents,
glycerol and its derivatives, bio-based solvents, and
8
–9
ionic liquids (ILs). Notwithstanding their value, the use of these solvents is still in its
early stages and is limited by a number of concerns.
Deep eutectic solvents (DESs), also known as deep eutectic ionic liquids (DEILs), or
low-melting mixtures (LMMs), or low transition temperature mixtures (LTTMs) in the
literature, have become more attractive due to their interesting properties and benefits.
Among these are the low cost of components, ease of preparation, tunable physico-
chemical properties, negligible vapor pressure, nontoxicity, bio-renewability and bio-
degradability. In fact, DESs have several features in common with ionic liquids. They
have a large number of molecular components which are typically hydrogen bond
donors. They are more industrially promising than ionic liquids due to their low cost
and tolerance to humidity, thus avoiding potential problems of hydrolysis or hygrosco-
1
0–11
picity.
DESs are defined as combinations of two or three safe and cheap compo-
nents which are capable of self-association, to form a eutectic mixture, which is a liquid
ꢀ
at temperatures lower than 100 C, with a melting point lower than that of each of the
individual components.
1
2
Multicomponent reactions (MCRs) have emerged as a powerful strategy for the syn-
thesis of numerous desirable chemical compounds, notably including natural products
and biologically active compounds. Moreover, MCRs have such advantages as oper-
ational simplicity, high atom-economy, reduced production of waste, and the avoidance
1
3–16
of intricate purification processes.
Carrying out MCRs in water as the reaction medium would be one of the most suit-
able methods, going a long way toward the fulfilment of the goals of green chemistry.
Use of water not only diminishes the risk of organic solvents but also improves the rate
1
7–18
of many chemical reactions.
CONTACT Behrooz Maleki
b.maleki@hsu.ac.ir
Department of Chemistry, Hakim Sabzevari University, Sabzevar,
Faculty of Chemistry, Shahrood University of
9
6179-76487, Iran; Ali Keivanloo
keivanloo@shahroodut.ac.ir
Technology, Shahrood, Iran
ß 2020 Taylor & Francis Group, LLC

2
H. ATHARIFAR ET AL.
Scheme 1. Synthesis of 3,4-disubstituted isoxazole-5(4H)-one derivatives.
Isoxazole derivatives are important heterocyclic compounds that possessing numerous
1
9
20
21
pharmacological and biological activities such as anti-HIV, antifungal, analgesic,
2
2
23
24
25
antitumor, COX-2 inhibitory, antiviral, and antioxidant properties.
Several procedures have been reported in the literature for the synthesis of 3,4-disub-
26
stituted isoxazol-5(4H)-ones. Among these we may note Fe O nanoparticles, citric
2
30
3
2
7
28
29
31
acid, sodium silicate, sodium benzoate, sodium sulfide, boric acid, potassium
3
2
33
34
35
36
phthalimide (PPI), phthalimide N-oxyl salts, Ag/SiO2, DABCO, pyridine, 2-
3
7
38
hydroxy-5-sulfobenzoic acid (2-HSBA), Dowex1-x8OH resin, montmorillonite K10
supported Sn composite (Sn -MontK10), imidazole, hydroxyapatite (HAp) nano-
II
II
39
40
4
1
42
43
particles, K CO , and LiBr.
2
3
It is thus of considerable interest that DESs based on choline chloride have been used
4
4–47
in an increasing number of organic reactions.
gram in green chemistry,
As part of our ongoing research pro-
4
8–59
we now report on the use of a DES based on choline
chloride and glycerol (ChCl/Gly) for the synthesis of 3,4-disubstituted isoxazole-5(4H)-
ones in water (Scheme 1). To the best of our knowledge, there are no citations in the
literature on the synthesis of compounds 4 using DESs. We sought an organic reaction
enhancement methodology, which would be faster and greener than other methods.
In order to obtain the best conditions for our reaction, we optimized the parameters
ꢀ
as listed in Table 1. It is observed that water/60 C gave the best result for this trans-
formation in the presence of ChCl/Gly (entry 1). This reaction was carried out in the
lone presence of either choline chloride or glycerol and gave low yields after 20 min
(entries 9, 10). In the absence of ChCl/Gly, no significant product formation was
observed even after 40 min (entry 11).
The optimized conditions were then used for different aldehydes to test the generality
of the work. The results are summarized in Table 2. Substituted aromatic aldehydes
containing electron-withdrawing groups or electron-donating groups underwent this
multicomponent synthesis with hydroxylamine hydrochloride and ethyl acetoacetate to
afford 3,4-disubstituted isoxazole-5(4H)-ones in excellent yields (mean yield 92%).
In order to show the characteristics of this method, we have compared our results
with results from other sources in the literature. The data listed in Table 3 show that
the DES ChCl/Gly was a very suitable catalyst for this transformation, with dramatically
shorter reaction times than some methods. It is also noteworthy that ChCl/Gly, is inex-
pensive compared with other catalysts.
In conclusion, a green and simple synthesis of 3,4-disubstituted isoxazole-5(4H)-ones
using the DES ChCl/Gly is reported. The advantages of the present procedure are
experimental simplicity, easy work-up, and high yields of products. Furthermore, this
procedure is sustainable because of the efficiency of the readily available and bio-
degradable deep eutectic solvent.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
3
a
Table 1. Optimization of reaction conditions for 4a.
Entry
Catalyst (ml or g)
Conditions
Time (min)
Yield (%)
ꢀ
1
2
3
4
5
6
7
8
9
ChCl/Gly (0.2 ml)
ChCl/Gly (0.2 ml)
ChCl/Gly (0.2 ml)
ChCl/Gly (0.2 ml)
ChCl/Gly (0.2 ml)
ChCl/Gly (0.2 ml)
ChCl/Gly (0.3 ml)
ChCl/Gly (0.1 ml)
ChCl (0.04 g)
Water/60 C
20
20
20
20
20
20
20
20
20
20
40
95
78
89
64
90
35
92
84
21
48
ꢀ
Ethanol/60 C
Water/Ethanol (2:1, v/v)/60 C
ꢀ
ꢀ
Solvent-free/60 C
ꢀ
Water/50 C
Water/rt
ꢀ
Water/60 C
ꢀ
Water/60 C
ꢀ
Water/60 C
ꢀ
1
1
a
0
1
Gly (0.1 ml)
Water/60 C
b
ꢀ
c
–
Water/60 C
–
Reaction conditions: benzaldehyde (1 mmol), hydroxylamine hydrochloride (1 mmol) and ethyl acetoacetate (1 mmol) in
0
.1 ml water.
b
c
This reaction was carried out in the absence of ChCl/Gly.
No product 4a observed.
Experimental section
All starting materials and DES components were commercially available and purchased from
Merck. Melting points were determined on Electrothermal 9200 apparatus and are uncor-
rected. IR spectra were recorded as KBr pellets on a Shimadzu 435-U-04 spectrophotometer.
1
13
H and C NMR spectra were determined on a Bruker DRX-300 Avance spectrometer using
CDCl or DMSO-d , and shifts are given in ppm downfield from tetramethylsilane (TMS) as
3
6
an internal standard. All the reactions were monitored with thin layer chromatography (silica
gel, eluting solvents: n-hexane/ethyl acetate) and UV light as detecting agent.
Preparation of ChCl/Gly
The preparation of the DES involved the reaction of choline chloride (1 mol) with gly-
ꢀ
cerol (2 mol) at 100 C in a flask with stirring for 2 h to produce a clear solution. Thus
11
was suitable for the reactions without purification.
General procedure for the synthesis of 3,4-disubstituted isoxazole-5(4H)-ones (4a-l)
ChCl/Gly (0.1 ml) was added to a mixture of the aldehyde (1 mmol), ethyl acetoacetate
(
1 mmol) and hydroxylamine hydrochloride in a test tube. Water (0.1 mL) was added
ꢀ
and the reaction mixture was stirred and heated at 60 C using an oil bath for heating
(
for solid aldehydes, 10 drops of ethanol was added). The progress of reaction was con-
trolled by TLC (silica gel, n-hexane/ethyl acetate: 4/1). After completing the reaction,
mL water was added to the reaction mixture and the solid was filtered. The products
were recrystallized from ethanol (96%) to give pure compounds 4a-l. All of the products
5

4
H. ATHARIFAR ET AL.
Table 2. Green synthesis of 3,4-disubstituted iIsoxazole-5(4H)-ones (4a–l) by ChCl/Gly in water.
ꢀ
mp ( C)
Entry
Products
Yield (%)
95
Time (min)
20
Found
Lit.
4
1
4
a
140-141
141-142
4
1
7
4
4
b
c
94
90
20
25
174-175
139-140
173-174
137-139
3
2
9
4
d
93
20
201-203
200-201
4
4
1
0
4
4
e
f
95
92
20
20
218-220
135-137
220-221
134-135
4
2
4
g
90
25
134-135
130-132
2
2
4
4
9
8
1
3
4
4
4
4
h
i
95
95
90
92
25
20
20
20
212-214
133-135
142-144
195-197
210-211
134-136
143-144
193-194
j
k
(continued)

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
5
Table 2. Continued.
ꢀ
mp ( C)
Entry
Products
Yield (%)
Time (min)
Found
Lit.
3
8
4
l
85
20
178-180
180-182
Table 3. Comparison of methods for the synthesis of 3,4-disubstituted isoxazole-5(4H)-ones.
Compounds
Conditions
Time (min)
Yield (%)
ꢀ
ChCl/Gly/Water/30 C (present work)
20
480
150
150
60
110
40
180
20
300
90
60
80
60
25
60
95
90
89
80
93
87
92
70
94
90
87
90
92
95
95
83
27
Citric acid/water/rt
28
Sodium silicate/water/rt
Sodium sulfide/ethanol/rt
3
0
3
4
Ag/SiO
2-HSBA/water/rt
2
/water/rt3
7
4a
ꢀ
39
Nano-MMT-Sn/water/ultrasonication/30
C
42
K
2
CO
3
/water/reflux
ꢀ
ChCl/Gly/Water/30 C (present work)
27
Citric acid/water/rt
2
9
Sodium benzoate/water/rt
3
4
Ag/SiO
-HSBA/water/rt
Dowex1-x8OH/water/rt
Imidazole/water/ultrasonication/30 C
2
/water/rt3
7
2
4b
38
ꢀ
40
42
K
2
CO
3
/water/reflux
were known compounds and were identified by matching their melting points with
those reported in the literature cited in Table 2. Characterization data for some repre-
sentative compounds are provided below.
3
-Methyl-4-(3-methoxyphenyl)methylene-isoxazole-5(4H)-one (4g)
1
HNMR (300 MHz, DMSO-d ); 2.38 (s, 3H, CH ), 3.83 (s, 3H, OMe), 7.22-7.25 (m, 1H,
6
3
ArH), 7.48-7.52 (m, 1H, ArH), 7.90-7.91 (m, 1H, ArH), 7.93 (s. 1H, ¼CH), 8.10 (s, 1H,
1
3
ArH); CNMR (75 MHz, DMSO-d ); 11.70, 56.71, 117.97, 119.47, 120.70, 127.12,
1
1
6
ꢁ
1
30.36, 134.14, 152.06, 159.50, 162.58, 166.30; IR (KBr, cm ): 3482, 3098, 2981, 1741,
622, 1477, 1571, 1440, 1278, 1170, 1051, 877, 775, 680.
3
-Methyl-4-(4-cyanophenyl)methylene-isoxazole-5(4H)-one (4k)
1
HNMR (300 MHz, DMSO-d ); 2.26 (s, 3H, CH ), 7.15 (d, 2H, ArH), 7.56 (s, 1H,
6
3
1
3
¼
CH), 8.52 (d, 2H, ArH); CNMR (75 MHz, DMSO-d ): 11.74, 115.13, 115.25, 115.69,
6
ꢁ
1
1
26.20, 137.37, 151.71, 161.72, 164.72, 169.08; IR (KBr, cm ): 3462, 3090, 2978, 2223,
731, 1590, 1434, 1279, 1170, 1021, 873, 560.
1
ORCID
Ali Keivanloo
http://orcid.org/0000-0003-1430-7399

6
H. ATHARIFAR ET AL.
Behrooz Maleki
http://orcid.org/0000-0002-0322-6991
References
1
2
. Y. L. Gu, Green Chem., 14, 2091 (2012). doi:10.1039/c2gc35635j
. B. Maleki, M. Baghayeri, S. M. Vahdat, A. Mohammadzadeh and S. Akhoondi, RSC Adv., 5,
6545 (2015). doi:10.1039/C5RA06618B
. Y. Medina-Gonzalez, S. Camy and J. S. Condoret, ACS Sustainable Chem. Eng., 2, 2623
2014). doi:10.1021/sc5004314
4
3
4
(
. B. Maleki, M. Raei, E. Akbarzadeh, H. Ghasemnejad Borsa, A. Sedrpoushan, S. Sedigh
Ashrafi and M. N. Dehdashti, Org. Prep. Proced. Int., 48, 62 (2016). doi:10.1080/00304948.
2016.1127102
5. B. Maleki, S. S. Ashrafi and R. Tayebee, RSC Adv., 4, 41521 (2014). doi:10.1039/C4RA04654D
6. F. He, P. Li, Y. L. Gu and G. X. Li, Green Chem., 11, 1767 (2009). doi:10.1039/b916015a
7. Y. L. Gu and F. Jerome, Chem. Soc. Rev., 42, 9550 (2013). doi:10.1039/c3cs60241a
8. B. Maleki, G. Esmailian and R. Tayebee, Org. Prep. Proced. Int., 47, 461 (2015). doi:10.1080/
0
0304948.2015.1088757
. B. Maleki, E. Akbarzadeh and S. Babaee, Dyes Pigm., 123, 222 (2015). doi:10.1016/j.dyepig.
015.08.009
9
2
1
1
0. P. Liu, J. W. Hao, L. P. Mo and Z. H. Zhang, RSC Adv., 5, 48675 (2015). doi:10.1039/C5RA05746A
1. L. Zare Fekri, M. Nikpassand, S. Mostaghim and O. Marvi, Org. Prep. Proced. Int., 52, 81
(
2020). doi:10.1080/00304948.2020.1714319
1
1
2. X. Ge, C. Gu, X. Wang and J. Tu, J. Mater. Chem. A 5, 8209 (2017). doi:10.1039/C7TA01659J
3. B. Maleki, R. Rooky, E. Rezaei Seresht, R. Tayebee, Org. Prep. Proced. Int., 49, 557 (2017).
doi:10.1080/00304948.2017.1384282
1
1
4. B. Maleki, Org. Prep. Proced. Int., 48, 303 (2016). doi:10.1080/00304948.2016.1165061
5. B. Maleki, H. Alinezhad, H. Atharifar, R. Tayebee and A. Vedad Mofrad, Org. Prep. Proced.
Int., 51, 301 (2019). doi:10.1080/00304948.2019.1600132
16. B. Maleki, R. Tayebee, M. Kermanian and S. Sedigh Ashrafi, J. Mex. Chem. Soc., 57, 290
(
2013). doi:10.29356/jmcs.v57i4.192
7. H. Alinezhad, M. Tarahomi, B. Maleki and A. Amiri, Appl. Organometal. Chem., 33, e4661
2019). doi:10.1002/aoc.4661
1
(
1
1
8. M. Tarahomi, H. Alinezhad and B. Maleki, Appl. Organometal. Chem., 33, e5203 (2019).
9. B. L. Deng, M. D. Cullen, Z. Zhou, T. L. Hartman, R. W. Buckheit, C. Pannecouque, E. D.
Clercq, P. E. Fanwick and M. Cushman, Bioorg. Med. Chem., 14, 2366 (2006). doi:10.1016/j.
bmc.2005.11.014
2
2
2
2
0. M. M. M. Santos, N. Faria, J. Iley, S. J. Coles, M. B. Hursthouse, M. L. Martins and R.
Moreira, Bioorg. Med. Chem. Lett., 20, 193 (2010). doi:10.1016/j.bmcl.2009.10.137
1. H. Kan, I. Adachi, R. Kido and K. Hirose, J. Med. Chem., 10,411 (1967). doi:10.1021/
jm00315a028
2. P. Diana, A. Carbone, P. Barraja, G. Kelter, H. H. Fiebig and G. Cirrincione, Bioorg. Med.
Chem., 18, 4524 (2010). doi:10.1016/j.bmc.2010.04.061
3. J. J. Talley, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, W. E.
Perkins, R. S. Rogers, A. F. Shaffer, Y. Y. Zhang, B. S. Zweifel and K. Seibert, J. Med. Chem.,
4
3, 775 (2000). doi:10.1021/jm990577v
2
2
2
4. Y. S. Lee, S. M. Park and B. H. Kim, Bioorg. Med. Chem. Lett., 19, 1126 (2009). doi:10.1016/
j.bmcl.2008.12.103
5. A. Padmaja, C. Rajasekhar, A. Muralikrishna and V. Padmavathi, Eur. J. Med. Chem., 46,
5
034 (2011). doi:10.1016/j.ejmech.2011.08.010
6. S. Fozooni, N. G. Hosseinzadeh, H. Hamidian, and M. R. Akhgar, J. Brazil. Chem. Soc. 24,
649 (2013).
1
2
2
7. A. B. Rikani and D. Setamdideh, Orien. J. Chem. 32, 1433 (2016). doi:10.13005/ojc/320317
8. Q. Liu and R. T. Wu, J. Chem. Res., 35, 598 (2011). doi:10.3184/174751911X13176501108975

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
7
2
9. Q. Liu and Y. N. Zhang, Bull. Korean Chem. Soc., 32, 3559 (2011). doi:10.5012/bkcs.2011.32.
0.3559
0. Q. Liu and X. Hou, Phosphorus Sulfur Silicon Relat. Element., 187, 448 (2012). doi:10.1080/
0426507.2011.621003
1
3
1
31. H. Kiyani and F. Ghorbani, Res. Chem. Intermed., 41, 2653 (2015). doi:10.1007/s11164-013-1411-x
32. H. Kiyani and F. Ghorbani, J. Saudi Chem. Soc., 21, S112 (2017). doi:10.1016/j.jscs.2013.11.002
33. M. G. Dekamin and S. Z. Peyman, Monatsh. Chem., 147, 445 (2016). doi:10.1007/s00706-015-1565-x
34. S. N. Maddila, S. Maddila, W. E. Van Zyl and S. B. Jonnalagadda, Res. Chem. Intermed., 42,
2553 (2016). doi:10.1007/s11164-015-2167-2
35. M. Mirzazadeh and G. H. Mahdavinia, E-J. Chem., 9, 425 (2012). doi:10.1155/2012/562138
36. K. Ablajan and H. Xiamuxi, Chin. Chem. Lett., 22, 151 (2011). doi:10.1016/j.cclet.2010.09.023
37. H. Kiyani, H. Darbandi, A. Mosallanezhad and F. Ghorbani, Res. Chem. Intermed., 41, 7561
(
2015). doi:10.1007/s11164-014-1844-x
38. D. Setamdideh, J. Serb. Chem. Soc., 81, 971 (2016). doi:10.2298/JSC160202050S
39. M. Ahmadzadeh, Z. Zarnegar and J. Safari, Green Chem. Lett. Rev., 11, 78 (2018). doi:10.
1080/17518253.2018.1434564
4
4
0. J. Safari, M. Ahmadzadeh and Z. Zarnegar, Z. Org. Chem. Res., 2, 134 (2016).
1. B. Maleki, M. Chahkandi, R. Tayebee, S. Kahrobaei, H. Alinezhad and S. Hemmati, Appl.
Organomet. Chem., 33, e5118 (2019).
4
4
4
4
4
4
4
4
2. R. Laroum, R. Boulcina, C. Bensouici and A. Debache, Org. Prep. Proced. Int., 51, 583
(
2019). doi:10.1080/00304948.2019.1677993
3. G. Ferouani, A. Nacer, N. Ameur, R. Bachir and C. Ziani-Cherif, J. Chin. Chem. Soc., 65, 459
2018). doi:10.1002/jccs.201700334
(
4. N. Azizi, S. Dezfooli and M. Mahmoudi Hashemi, J. Mol. Liq., 62, 194 (2014). doi:10.1016/j.
molliq.2014.01.009
5. R. Mancuso, A. Maner, L. Cicco, F. M. Perna, V. Capriati and B. Gabriele, Tetrahedron 72,
4239 (2016). doi:10.1016/j.tet.2016.05.062
6. M. K. AlOmar, M. Hayyan, M. A. Alsaadi, S. Akib, A. Hayyan and M. A. Hashim, J. Mol.
Liq., 215, 98 (2016). doi:10.1016/j.molliq.2015.11.032
7. N. Azizi, M. Khajeh and M. Alipour, Ind. Eng. Chem. Res., 53, 15561 (2014). doi:10.1021/
ie502019z
8. B. Maleki, M. Raei, H. Alinezhad, R. Tayebee and A. Sedrpoushan, Org. Prep. Proced. Int.,
5
0, 288 (2018). doi:10.1080/00304948.2018.1462055
9. B. Maleki, F. Mohammadi Zonos and H. A. Akhlaghi, Org. Prep. Proced. Int., 47, 361 (2015).
doi:10.1080/00304948.2015.1066646
50. B. Maleki and S. Sheikh, Org. Prep. Proced. Int., 47, 368 (2015). doi:10.1080/00304948.2015.1066647
51. B. Maleki, Org. Prep. Proced. Int., 47, 173 (2015). doi:10.1080/00304948.2015.1005990
52. B. Maleki and F. Taimazi, Org. Prep. Proced. Int., 46, 252 (2014). doi:10.1080/00304948.2014.903143
53. A. Khojastehnezhad, B. Maleki, B. Karrabi and E. Rezaei Seresht, Org. Prep. Proced. Int., 49,
338 (2017). doi:10.1080/00304948.2017.1342505
5
5
5
5
5
5
4. H. Veisi, A. Naeimi, B. Maleki, S. Sedigh Ashrafi and A. Sedrpoushan, Org. Prep. Proced.
Int., 47, 309 (2015). doi:10.1080/00304948.2015.1052321
5. S. Hemmati, P. Mohammadi, A. Sedrpoushan and B. Maleki, Org. Prep. Proced. Int., 50, 465
(
2018). doi:10.1080/00304948.2018.1525668
6. B. Maleki, O. Reiser, E. Esmaeilnezhad and H. J. Choi, Polyhedron 162, 129 (2019). doi:10.
016/j.poly.2019.01.055
1
7. B. Maleki, R. Nejat, H. Alinezhad, S. M. Mousavi, B. Mahdavi and M. Delavari, Org. Prep.
Proced. Int., accepted for publication.
8. B. Maleki and H. Veisi, Org. Prep. Proced. Int., 52, 232 (2020). doi:10.1080/00304948.2020.
1
752606
9. F. Adibian, A. R. Pourali, B. Maleki, M. Baghayeri and A. Amiri, Polyhedron 175, 114179
2020). doi:10.1016/j.poly.2019.114179
(