Multicomponent green synthesis, spectroscopic and structural investigation of multi-substituted imidazoles. Part 1

Article abstract of DOI:10.1515/znb-2015-0067

Ten 1,2,4,5-tetra-substituted imidazole derivatives have been synthesized with a 2-hydroxyethy substituent at the 1-nitrogen atom and potentially electron releasing hydroxy-, methoxy-, dimethylamino- or nitro substituents in various positions on the benzene ring located on the 2-carbon atom. The prototypical derivative with an unsubstituted phenyl ring at the 2-position is also reported. The compounds are obtained in excellent yields (average 86 %) via a four-component cyclocondensation reaction of benzil, ethanolamine, and the appropriate aromatic carbaldehyde together with ammonium acetate. The reaction uses a novel ionic liquid catalyst, DEAHS (diethyl ammonium hydrogen sulfate), under solventfree conditions and a green synthetic protocol. The key advantages of this process are high yield, shorter reaction times and ease of work-up. Fürthermore, the products can be purified by a non-chromatographic method and the catalyst is re-usable. All of these newly synthesized compounds have been characterized from spectral data; the X-ray structures of three representative molecules are also detailed.

Full text of DOI:10.1515/znb-2015-0067

Z. Naturforsch. 2015; 70(11)b: 809–817
Shaaban K. Mohamed*, Jim Simpson, Adel A. Marzouk, Avtandil H. Talybov,
Antar A. Abdelhamid, Yusif A. Abdullayev and Vagif M. Abbasov
Multicomponent green synthesis, spectroscopic
and structural investigation of multi-substituted
imidazoles. Part 1
DOI 10.1515/znb-2015-0067
Keywords: Brønsted acids; green chemistry; imidazoles;
ionic liquid; molecular structures; multicomponent
reactions.
Received April 6, 2015; accepted June 17, 2015
Abstract: Ten 1,2,4,5-tetra-substituted imidazole deriva-
tives have been synthesized with a 2-hydroxyethy sub-
stituent at the 1-nitrogen atom and potentially electron
releasing hydroxy-, methoxy-, dimethylamino- or nitro 1 Introduction
substituents in various positions on the benzene ring
located on the 2-carbon atom. The prototypical derivative Imidazoles are an important class of heterocycles being
with an unsubstituted phenyl ring at the 2-position is also the core fragment of numerous natural products and bio-
reported. The compounds are obtained in excellent yields logical systems [1]. In general, compounds incorporating
(average 86ꢀ%) via a four-component cyclocondensation imidazole moieties play important roles in biochemical
reaction of benzil, ethanolamine, and the appropriate processes and display significant pharmacological prop-
aromatic carbaldehyde together with ammonium acetate. erties [2]. Various substituted imidazole derivatives have
The reaction uses a novel ionic liquid catalyst, DEAHS also been found to have important biological functions
(diethyl ammonium hydrogen sulfate), under solvent- acting as anti-helminthic, analgesic, antibacterial, anti-
free conditions and a green synthetic protocol. The key fungal, antiviral, tuberculostatic, cytostatic, and anti-
advantages of this process are high yield, shorter reaction inflammatory agents [3].
times and ease of work-up. Furthermore, the products
Multicomponent reactions (MCRs) have excited a
can be purified by a non-chromatographic method and great deal of interest among chemists and pharmacists
the catalyst is re-usable. All of these newly synthesized due to their outstanding status in modern organic synthe-
compounds have been characterized from spectral data; sis and medicinal chemistry. MCRs are one-pot processes
the X-ray structures of three representative molecules are bringing together three or more reaction components with
also detailed.
high atom economy and good selectivity [4, 5]. Develop-
ing new MCRs [6] and improving known multi-component
reactions are areas of considerable current interest and
MCR processes leading to imidazole derivatives are no
exception. The presence of imidazole rings in so many
biologically important natural products and pharmaco-
logically active compounds has spawned a diverse array
of synthetic approaches to the production of these hetero-
cycles [7], the majority being classical methods [8–10]. In
particular, tetrasubstituted imidazoles and their deriva-
tives have been synthesized by several methods [11–14]. In
addition, such syntheses are usually carried out in polar
organic solvents such as ethanol, methanol, acetic acid,
DMF and DMSO and involve complex isolation require-
ments, side products and tedious recovery procedures.
Despite intensive efforts to improve these syntheses, only
a handful of general methods exist for the construction
of tetrasubstituted imidazoles. These include reactions
*Corresponding author: Shaaban K. Mohamed, Chemistry and
Environmental Division, Manchester Metropolitan University,
Manchester, M1 5GD, England; and Faculty of Science, Chemistry
Department, Minia University, 61519 El-Minia, Egypt,
e-mail: shaabankamel@yahoo.com
Jim Simpson: Department of Chemistry, University of Otago,
P. O. Box 56, Dunedin, New Zealand
Adel A. Marzouk: Faculty of Pharmacy, Pharmaceutical Chemistry
Department, Al Azhar University, Egypt
Avtandil H. Talybov and Vagif M. Abbasov: Mamedaliev Institute
of Petrochemical Processes, National Academy of Sciences of
Azerbaijan, Baku, Azerbaijan
Antar A. Abdelhamid: Faculty of Science, Department of Chemistry,
Sohag University, 82524 Sohag, Egypt
Yusif A. Abdullayev: Mamedaliev Institute of Petrochemical
Processes, National Academy of Sciences of Azerbaijan, Baku,
Azerbaijan; and Department of Chemical Engineering, Qafqaz
University, Baku, Azerbaijan
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810ꢀ ꢀS. K. Mohamed et al.: Multicomponent green synthesis, spectroscopic and structural investigation
catalyzed by silica gel or Zeolite HY [15], silica gel-NaHSO4 complexes of the imidazole derivatives are excluded.
[16], molecular iodine [17], K5CoW12O40·3H2O [18], hetero- However, only five structures of 2,4,5-triphenyl-substi-
polyacids [19] and HClO4-SiO2 [20]. BF3, as a strong Lewis tuted imidazole derivative with a alcohol substituents on
the imidazole sp3
acid, has also been used in both small and large scale reac-
-N atom have been reported. One of these
tions as an acid catalyst [21]. All of these processes gen- [39] is compound 2e in this paper, with details of the spec-
erate waste containing both catalyst and solvent, which troscopic identification of this molecule included here
must be recovered, treated and disposed of. The toxicity for completeness and comparison with the other, similar
and volatile nature of many organic solvents, particularly derivatives. Two other related compounds have 2-hydroxy-
chlorinated hydrocarbons, which are widely used in huge propyl substituents [40, 41], with 3-phenylpropan-1-ol
amounts for organic reactions, have posed a serious threat substituents on the sp3-N atom in the two other similar
to the environment [22]. Thus, the design of solvent-free compounds [42, 43]. Interestingly, only ten other struc-
catalytic reactions has received tremendous attention in tures in the database have alkyl chains of two or more C
recent times in the area of green synthesis [23, 24].
atoms on the 1-nitrogen atom of the imidazole [44–52],
Ionic liquid (IL) technology offers a new and envi- with simple aliphatic chains predominating and with no
ronmentally benign approach toward modern synthetic other alcohol derivatives.
chemistry. Ionic liquids have interesting advantages such
as extremely low vapor pressure, excellent thermal stabil-
ity, reusability and the ability to dissolve many organic and
2 Results and discussion
inorganic substrates [25]. Ionic liquids have been success-
fully employed as solvents and catalysts for a variety of
reactions [26–29] which promise widespread applications 2.1 Synthetic procedures
in both small and large scale organic syntheses. In a con-
tinuation of our efforts to develop Lewis and Brønsted acid In order to determine the most appropriate reaction condi-
catalyzed synthetic methodologies [30–33] and further to tions and to evaluate the catalytic efficiency of the ionic
our study of the synthesis of bio-active molecules [34–36] liquid diethyl ammonium hydrogen sulfate (DEAHS) [53],
we report herein a simple and environmentally friendly an initial model study was carried out on the synthesis of
MCR technique for the synthesis of potentially bio-active 1,2,4,5-tetrasubstituted imidazoles. Among the tested sol-
tetrasubstituted imidazole compounds (Scheme 1) in high vents were methanol, ethanol, DMF and DMSO; a solvent-
yields using the novel Brønsted acidic ionic liquid, diethyl free system was also investigated. Condensation of benzil,
ammonium hydrogen sulfate (DEAHS) as a catalyst for the benzaldehyde, ethanolamine, and ammonium acetate to
first time.
form 2-(2,4,5-triphenyl-1H-imidazol-1-yl)ethanol (2a) was
Because of the pharmaceutical potential of these found to be significantly more facile under solvent-free
products, the structures of three representative deriva- conditions and proceeded to give the highest yield in a
tives have been determined by X-ray crystallography and relatively very short time, Table 1.
are reported here. Structures of 2,4,5-triphenyl-substituted
Additionally, we sought to evaluate the generality of
imidazole compounds are reasonably common with 214 this process for the synthesis of a broad range of deriva-
hits in the Cambridge Structural Database (CSD) [37], tives with a variety of substituents on the phenyl ring at
including the archetypal lophine (2,4,5-triphenyl-1H-im- the 2-position of the imidazole ring, Scheme 1. Thus,
idazole) [38]. This number drops to 180 if coordination reactions of benzil (10 mmol), with various aromatic
R
O
H
N
O
O
HO
DEAHS
N
CH3COONH4
+
+
+
Solvent free
NH2
R
OH
1a–j
2a–j
Scheme 1:ꢀSynthesis of 2a–2j, Rꢁꢂ=ꢂꢁ H, 2a, 2-OH, 2b, 4-OH, 2c, 3-OCH3, 2d, 4-OCH3, 2e, 2,4-OCH3, 2f, 3,4-OCH3, 2g, 2,5-OCH3, 2h, 4-(CH3)2N,
2i and4-NO2, 2j.
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S. K. Mohamed et al.: Multicomponent green synthesis, spectroscopic and structural investigationꢃ
ꢃ811
Table 1:ꢀSynthesis of 2-(2,4,5-triphenyl-1H-imidazol-1-yl)ethanol
600
500
400
300
200
100
0
100
98
96
94
92
90
88
86
84
82
80
78
76
74
Time (min)
Yield (%)
(2a) using diethylammonium hydrogen sulfate (DEAHS) catalyst
(0.3 equiv) in different solvents.
Solvent
ꢁ
T (°C)
ꢁ Time
ꢁ Yield (%)
Methanol
Ethanol
Acetonitrile
DMF
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
67
78
ꢂ 3 h
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
40
45
35
55
60
98
ꢂ 3 h
67
ꢂ 3 h
100
100
100
ꢂ 2 h
DMSO
ꢂ 2 h
Solvent-free conditionsꢂ
ꢂ 20 min
CI
CV
Catalyst
CVII
CVIII
C
C
CVI
C
II
III
IV
aldehydes (10 mmol) bearing electron releasing groups
(such as hydroxyl, mono- and di-methoxy, or dimethyl
amino substituents), ethanolamine (11 mmol) and ammo-
nium acetate (10 mmol), were carried out in the presence
Fig. 1:ꢀDependence of the yield and time of reaction on the catalyst
type.
of diethylammonium hydrogen sulfate (0.5 g, 3 mmol) as ammonium acetate starting material. The resulting inter-
catalyst (Table 1). The yields of all the products so obtained mediate readily loses a water molecule to produce the
were very good to excellent. Furthermore, the reactions imine I (Scheme 2). Similarly the catalyst promotes an
proceeded without the formation of any side products, additional condensation reaction of one of the carbonyl
such as 2,4,5-trisubstituted imidazoles, which are normally groups from benzil with the aminoethanol reactant to
observed as an impediment to efficient synthesis under the furnish the imine II. DEAHS also catalyzes nucleophilic
influence of other strong acids [19, 20]. An earlier report attack by the imine I on the second carbonyl group in
of the preparation of (2a) used a similar preparative route, imine II followed by protonation to form the intermediate
but with l-proline triflate as the catalyst [54].
cation III. This in turn undergoes an intramolecular cycli-
The yield and reaction time for the formation of 2a has zation to give the unstable cyclic cation IV which elimi-
been recorded using different catalysts as listed in Table 2 nates water and then loses a proton to yield the target
and the results represented graphically in Fig. 1. While it is products 2a–2j. All products were fully characterized by
1
obvious that reaction temperatures will have a significant spectroscopic methods such as IR, H NMR, 13C NMR and
effect on reaction times, the data in Table 1 clearly confirm the structures of 2a, 2c and 2j were determined by X-ray
that DEAHS is indeed a highly efficient catalyst in terms of crystallography (see below).
both yield and reaction time when compared to other type
of catalysts that have been used.
Hydrogen bond formation between the carbonyl 2.2 Spectroscopic properties
group of the starting aldehyde and the catalyst DEAHS
makes the carbonyl very susceptible to nucleophilic The IR spectra of all of the compounds showed definitive
−1
attack by an ammonia molecule generated from the broad bands in the frequency range 3568–3144 cm for the
Table 2:ꢀComparison of the efficiency (yield and reaction time) of various catalysts with diethyl ammonium hydrogen sulfate in the
synthesis of the 2-(2,4,5-triphenyl-1H-imidazol-1-yl)ethanol, 2a.
No ꢁ
Catalyst
ꢁ
Conditions
ꢁ
Time (min)
ꢁ Yield (%)ꢁ
Refs.
CI
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
InCl3·3H2O
KH2PO4
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
MeOH, r. t.
ꢂ
ꢂ
ꢂ
ꢂ
492
60
360
120
540
60
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
76ꢂ
89ꢂ
80ꢂ
95ꢂ
87ꢂ
94ꢂ
89ꢂ
98ꢂ
[12]
CII
Reflux in EtOH
C10F18, 80ꢁ°C
Reflux in EtOH
[55]
CIII
CIV
CV
CVI
CVII
CVIII
Yb(OPf)3
Zr(acac)4
l-proline
[Hbim]BF4
[1]
[56]
Methanol, 60ꢁ°Cꢂ
100ꢁ°C
Reflux in EtOH
100ꢁ°C
[57]
ꢂ
ꢂ
ꢂ
[58]
NiCl2·6H2O-Al2O3ꢂ
90
20
[59]
+
−
Et2NH2 HSO4
ꢂ
this work
(deahs)
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812ꢀ
ꢀS. K. Mohamed et al.: Multicomponent green synthesis, spectroscopic and structural investigation
O
O
H
O
S
N
+
O
H
H
R
R
H
H2O
NH3
CH3COONH4
NH
O
H
I
O
O
H
O
S
N
O
H
H
R
H
Ph
Ph
O
O
H
HN
O
HO
Ph
Ph
H
C
R
H2O
N
+ H+
NH2CH2CH2OH
Ph
Ph
N-CH2CH2OH
N-CH2CH2OH
II
H
H
III
O
H
O
N
S
O
O
HO
Ph
Ph
NH
H
Ph
Ph
Ph
N
N
H+
H2O
N
H
C
R
R
C
N
Ph
N
R
CH2CH2OH
CH2CH2OH
CH2CH2OH
IV
Scheme 2:ꢀGeneral mechanism for the multi-component synthesis.
OH stretching vibration of the ethanolic OH groups of all inclinations of these benzene rings to the central imida-
nine compounds. The phenolic OH stretches for 2b and zole ring are also detailed in Table 3 which clearly shows
2c could not be distinguished separately from these vibra- that the benzene and imidazole rings are not co-planar in
tions. In addition, C–H stretching modes were found in any of the molecules.
the range 3084–3053 cm−1 while the Cꢁ=ꢁN stretching mode
The C2 benzene ring substituents differentiate the
of the imidazole unit was observed in a relatively narrow three molecules, starting with the prototypical compound
−1
range 1601–1603 cm for 2a–2h with the corresponding 2a with a simple phenyl ring in the 2-position. 4-Hydroxy
vibration for the dimethylamino substituted derivative 2i substitution is found in the C2 benzene ring of 2b, while
appearing at 1610 cm−1 while that for the 4-nitro derivative 2j has a nitro substituent at the 4-position of the C21…C26
−1
2j appeared at 1595 cm . The stretching vibrations of the benzene rings of each of the two unique molecules. These
−1
nitro group of 2j were observed at 1537 cm (asymmetri- are distinguished in the atom numbering by leading 1 and
cal) and 1338 cm−1 (symmetrical). Clearly the nature of the 2 characters; the two molecules differ principally in the
substituent on the 2-benzene ring has a noticeable effect inclination of the benzene rings at C2, C4 and C5 relative
on the vibrational spectra.
to the imidazole ring, (vide supra, Table 3). Also for 2j,
the planes of the nitro groups are inclined at 12.52(11)° for
molecule 1 and 4.3(3)° for molecule 2 to the planes of the
benzene ring to which they are bound.
2.3 Molecular and crystal structures of
2a, 2c and 2j
The molecular structures of the three compounds investi-
gated by X-ray crystallography are shown in Fig. 2 (i–iii). 3 Conclusion
The broad features of the three structures are sufficiently
similar to be discussed together. Each molecule com- We have developed a general procedure for the synthesis
prises a central imidazole ring substituted at N1 with a of tetrasubstituted imidazoles in high yield by a simple,
CH2CH2OH unit which generally lies almost orthogonal one-pot, four-component reaction of benzil, aldehydes,
to the imidazole ring, Table 3. The imidazole ring also ethanolamine and ammonium acetate utilizing diethyl-
carries an aromatic ring on each C atom with a substi- ammonium hydrogen sulphate (DEAHS) as a new ionic
tuted benzene ring on the C2 carbon atom for all but 2a liquid and catalyst. The reactions proceed in the absence
and simple phenyl substituents on C4 and C5. The relative of any solvent or additives. This protocol offers a broad
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Table 3:ꢀDihedral angles (deg) between the imidazole and benzene
ringsa for 2a, 2c and 2j.
Compound
ꢁ
1–2
ꢁ
1–3
ꢁ
1–4
2a
2c
ꢂ
ꢂ
53.76(19)
72.21(7)
42.82(4)
56.10(4)
ꢂ 21.02(15)
ꢂ 30.70(11)
ꢂ 71.31(19)
ꢂ
ꢂ
ꢂ
73.82(8)
70.19(4)
89.88(4)
2j (molecule 1)ꢂ
2j (molecule 2)ꢂ
ꢂ
ꢂ
22.91(3)
17.46(2)
aPlanes are numbered as follows: 1: N1,C2,N3,C4,C5; 2: C21…C26,
3: C41…C46; 4: C51…C56. For 2j, atom numbers defining the planes
have additional leading 1 and 2 characters for molecules 1 and 2,
respectively [Fig. 2 (iii)].
4 Experimental section
All reagents were purchased from Aldrich and Merck sup-
plier companies, and used without further purification.
Melting points were determined by the open capillary
method using a Gallenkamp melting point apparatus and
are uncorrected. CHN microanalyses were determined
using a Vario elemental analyzer (Shimadzu, Japan) at
the Organic Microanalysis Unit, Faculty of Science, Cairo
University, Cairo, Egypt. A SHIMADZU FT-IR-8400s spec-
trometer was used to record IR spectra as KBr pellets. NMR
spectra were recorded on a Bruker (300 and 400 MHz) Ultra
Shield NMR spectrometers with [D6]DMSO as the solvent.
Chemical shifts δ are given in ppm. The progress of the reac-
tions and purity of the products were monitored by TLC.
4.1 Synthesis of diethyl ammonium
hydrogen sulfate (DEAHS)
HSO4
NH2
Fig. 2:ꢀThe molecular structures of (i) 2a; (ii) 2c; (iii) the two unique
molecules in the asymmetric unit of 2j (crystallographic atom num-
bering and displacement ellipsoids drawn at the 50ꢁ% probability
level; H atoms as spheres with arbitrary radii).
Diethylamine(22.2g, 0.3mol)wasaddedintoa250mLthree-
necked flask with a magnetic stirrer. Then 29.4 g (0.3 mol)
concentrated sulfuric acid (98ꢀ%) was slowly added drop-
wise to the flask at room temperature then heated to 80ꢀ°C
for 12 h. The product was washed with diethyl ether three
scope for access to a wide spectrum of diversely substi- times to remove traces of non-ionic material. The residue
tuted 1,2,4,5-tetrasubstituted imidazoles. The absence of was dried under vacuum using a rotary evaporator to
toxic organic solvents from the entire process, multiple obtain the clear viscous product, diethyl ammonium hydro-
reusability of the catalyst, good product purity, sim- gen sulfate. Yield 98ꢀ%, pH 1.6 [53].
plicity in operation, and no requirement for chromato-
graphic purification, shorter reaction times and high
yields of products make this procedure greener, more 4.2 General method for the synthesis of
efficient and importantly cost effective. In view of their
1,2,4,5-tetrasubstituted imidazoles
pharmaceutical potential the molecular structures of
three representative compounds were also determined Benzil (10 mmol), an aldehyde (1a–1j) (10 mmol), ammo-
by X-ray diffraction.
nium acetate (10 mmol) and ethanolamine (11 mmol)
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814ꢀ ꢀS. K. Mohamed et al.: Multicomponent green synthesis, spectroscopic and structural investigation
were added to diethylammonium hydrogen sulfate (0.5 g, for C23H20N2O2 (356.4): C 77.51, H 5.66, N 7.89; found C 77.48,
3 mmol) in an oil bath at room temperature. The result- H 5.70, N 7.90ꢀ%.
ing mixtures were heated to 100ꢀ°C for the time reported
in Table 4. Reaction progress was monitored by TLC until
completion after 15–35 min. The reaction mixtures were 4.3.3 4-(1-(2-Hydroxyethyl)-4,5-diphenyl-1H-imidazol-
washed with water and the resulting solid products were
purified in all cases by recrystallization from ethanol.
2-yl)phenol (2c)
M. p. 287–289 oC. – FTIR (KBr): 3518 (OH), 3055 (C–H), 2985
(C–H), 2888 (C–H), 1603 (Cꢁ=ꢁN) 1503 (Cꢁ=ꢁC), 1452, 1169, 1067,
−1
1
4.3 Spectroscopic properties of 2a–2j
841, 707, 694 cm . – H NMR (300 MHz, [D6]DMSO, TMS):
δꢀꢁ=ꢁꢀ3.2 (t, 2H, CH2N), 3.95 (t, 2H, CH2O), 4.95 (s br., 1H,
CH2OH), 6.8–7.8 (m, Jꢀꢁ=ꢁꢀ8.8, 2.0 Hz, 14H, Ar-H), 10 (s br.,
1H, C6H4OH). – 13C NMR (300 MHz, [D6]DMSO): δꢀꢁ=ꢁꢀ46.8,
4.3.1 2-(2,4,5-Triphenyl-1H-imidazol-1-yl)ethanol (2a)
M. p. 184–185 oC. – FTIR (KBr): 3265 (OH), 3061 (C–H), 2964 59.7, 115.8, 122.3, 126.4, 126.6, 128.5, 129.2, 129.5, 129.7, 131.0,
(C–H), 1601 (Cꢁ=ꢁN) 1502 (Cꢁ=ꢁC), 1456, 1181, 1096, 834, 720, 131.5, 131.7, 135.3, 136.6, 147.9, 158.4. – Analysis for C23H20N2O2
1
696 cm−1. – H NMR (300 MHz, [D6]DMSO, TMS): δꢀꢁ=ꢁꢀ3.25 (356.4): C 77.51, H 5.66, N 7.89; found C 77.48, H 5.63, N 7.90ꢀ%.
(t, 2H, CH2N), 4.07 (t, 2H, CH2O), 5.07 (s, 1H, OH), 7.00–7.00
(m, Jꢀꢁ=ꢁꢀ8.8, 2.0 Hz, 15H, Ar-H). – 13C NMR (300 MHz, [D6]
DMSO): δꢀꢁ=ꢁꢀ46.9, 59.8, 126.6, 128.5, 129.0, 129.2, 129.3, 129.6, 4.3.4 2-(2-(3-Methoxyphenyl)-4,5-diphenyl-1H-imidazol-
130.3, 131.4, 131.6, 135.1, 137.1, 147.7. – Analysis for C23H20N2O
(340.4): C 81.16, H 5.92, N 8.23; found C 81.20, H 6.00, N
8.25ꢀ%.
1-yl)ethanol (2d)
M. p. 160–162 °C. – FTIR (KBr): 3334 (OH), 3064 (C–H), 2964
(C–H), 2836 (C–H), 1603 (Cꢁ=ꢁN), 1502 (Cꢁ=ꢁC), 1462, 1262, 1156,
1055, 873, 734, 698 cm . – H NMR (300 MHz, [D6]DMSO,
TMS): δꢀꢁ=ꢁꢀ3.247 (t, 2H, CH2N), 3.824 (s, 3H, OCH3), 4.005
(t, 2H, CH2O), 4.89 (s br, 1H, CH2OH), 7.109–7.542 (m, 14H,
Ar-H). – 13C NMR (300 MHz, [D6]DMSO): δꢀꢁ=ꢁꢀ46.5, 55.2, 59.3,
−1
1
4.3.2 2-(1-(2-hydroxyethyl)-4,5-diphenyl-1H-imidazol-
2-yl)phenol (2b)
o
M. p. 287–289 C. – FTIR (KBr): 3518 (OH), 3055 (C–H), 114.5, 121.3, 126.1, 126.1, 128.0, 128.9, 129.1, 129.6, 129.8, 131.0,
2985 (C–H), 2888 (C–H), 1603 (Cꢁ=ꢁN) 1503 (Cꢁ=ꢁC), 1452, 131.1, 132.5, 146.9, 159.2. – Analysis for C24H22N2O2 (370.5): C
−1
1
1169, 1067, 841, 707, 694 cm . – H NMR (300 MHz, [D6] 74.56, H 5.99, N 7.60; found C 74.60, H 6.01, N 7.58ꢀ%.
DMSO, TMS): δꢀꢁ=ꢁꢀ3.2 (t, 2H, CH2N), 3.95 (t, 2H, CH2O), 4.95
(s br., 1H, CH2OH), 6.8–7.8 (m, Jꢀꢁ=ꢁꢀ8.8, 2.0 Hz, 14H, Ar-H),
10 (s br., 1H, C6H4OH). – 13C NMR (300 MHz, [D6]DMSO): 4.3.5 2-(2-(4-Methoxy)-4,5-diphenyl-1H-imidazol-1-yl)
δꢀꢁ=ꢁꢀ46.8, 59.7, 115.8, 122.3, 126.4, 126.6, 128.5, 129.2, 129.5,
ethanol (2e)
129.7, 131.0, 131.5, 131.7, 135.3, 136.6, 147.9, 158.4. – Analysis
M. p. 187–188 oC. – FTIR (KBr): 3159 (OH), 3058 (C–H), 2965
(C–H), 2836 (C–H), 1603 (Cꢁ=ꢁN), 1466 (Cꢁ=ꢁC),1179, 1081,
1
834, 721, 695 cm−1. – H NMR (300 MHz, [D6]DMSO, TMS):
Table 4:ꢀReaction time, yield and physical properties of compounds
2a–2j.
δꢀꢁ=ꢁꢀ3.25 (t, 2H, CH2N), 4.0 (t, 2H, CH2O), 5.07 (s, 1H, OH),
7.03–7.7 (m, Jꢀꢁ=ꢁꢀ8.8, 2.0 Hz, 14H, Ar-H). – 13C NMR (300 MHz,
[D6]DMSO): δꢀꢁ=ꢁꢀ46.8, 55.6, 59.8, 114.4, 123.9, 126.5, 126.6,
128.5, 129,3, 129.5, 129.9, 131.0, 131.4, 131.6, 135.2, 136.8,
147.6. – Analysis for C24H22N2O2 (370.5): C 74.56, H 5.99, N
7.60; found C 74.65, H 6.02, N 7.57ꢀ%.
No.ꢁ
R
ꢁ
Mol. Formula (Mr
in parentheses)
ꢁ
M. p. (°C) ꢁ Time ꢁ Yield
(min)
(%)
2a ꢂ
H
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
C23H20N2O (340.4) ꢂ 184–185
C23H20N2O2 (356.4)ꢂ 108–110
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
20
25
15
35
30
30
35
35
35
15
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
98
92
92
82
95
88
92
92
93
85
2b ꢂ 2-OH
2c ꢂ 4-OH
C23 20
C24 22
C24 22
H
N2O2 (356.4)ꢂ 287–289
N2O2 (370.4)ꢂ 160–162
N2O2 (370.4)ꢂ 187–188
N2O3 (401.5)ꢂ 175–177
N2O3 (401.5)ꢂ 212–214
N2O3 (401.5)ꢂ 198–200
N3O (383.5) ꢂ 207–209
N3O3 (385.4)ꢂ 190–192
2d ꢂ 3-OCH3
2e ꢂ 4-OCH3-
H
H
4.3.6 2-(2-(2,4-Dimethoxyphenyl)-4,5-diphenyl-1H-
2f ꢂ 2,4-CH3O-ꢂ C25 25
H
2g ꢂ 3,4-CH3O-ꢂ C25 25
2h ꢂ 2,5-OCH3-ꢂ C25 25
2i 4-(CH3)2N-ꢂ C25 25
2j 4-NO2- C23 19
H
imidazol-1-yl)ethanol (2f)
H
ꢂ
ꢂ
H
M. p. 175–177 °C. – FTIR (KBr): 3153 (OH), 3060 (C–H), 2980
(C–H), 2837 (C–H), 1614 (Cꢁ=ꢁN) 1579 (Cꢁ=ꢁC), 1454, 1258, 1153,
ꢂ
H
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S. K. Mohamed et al.: Multicomponent green synthesis, spectroscopic and structural investigationꢃ
ꢃ815
−1
1
1072, 837, 720, 701 cm . – H NMR (300 MHz, [D6]DMSO, – Analysis for C25H25N3O (383.5): C 78.30, H 6.57, N 10.96;
TMS): δꢀꢁ=ꢁꢀ3.73 (s, 6H, 2CH3O), 3.78 (t, 2H, CH2N), 4.00 (t, found C 78.32, H 6.60, N 11.00ꢀ%.
2H, CH2O), 4.97 (s br, 1H, CH2OH), 7.02–7.60 (m, 13H, Ar-H).
–
13C NMR (300 MHz, [D6]DMSO): δꢀꢁ=ꢁꢀ46.8, 55.7, 55.7, 59.7,
4.3.10 2-(2-(4-Nitrophenyl)-4,5-diphenyl-1H-imidazol-
111.8, 113.3, 122.1, 123.8, 126.4, 126.7, 128.3, 129.1, 129.4, 129.9,
131.5, 131.5, 134.9, 136.7, 147.9, 148.9, 149.8. – Analysis for
C25H25N2O3 (401.5): C 74.79, H 6.28, N 6.98; found C 74.77, H
6.30, N 7.02ꢀ%.
1-yl)ethanol (2j)
o
M. p. 190–192 C. – FTIR (KBr): 3144 (OH), 3084 (C–H),
2961 (C–H), 2849 (C–H), 1595 (Cꢁ=ꢁN) 1524 (Cꢁ=ꢁC), 1479, 1286,
−1
1
1128, 1060, 875, 734, 692 cm . – H NMR (300 MHz, [D6]
DMSO, TMS): δꢀꢁ=ꢁꢀ3.27 (t, 2H, CH2N), 4.08 (t, 2H, CH2O),
5.00 (s br, 1H, CH2OH), 7.00–8.52 (m, 14H, Ar-H). – 13C NMR
(300 MHz, [D6]DMSO): δꢀꢁ=ꢁꢀ47.5, 59.9, 124.2, 126.7, 126.9,
128.6, 129.6, 130.3, 131.1, 131.4, 134.7, 137.9, 148.1, 145.6, 147.5.
– Analysis for C23H19N3O3 (385.4): C 71.68, H 4.97, N 10.90;
found C 71.71, H 5.00, N 10.88ꢀ%.
4.3.7 2-(2-(3,4-Dimethoxyphenyl)-4,5-diphenyl-1H-
imidazol-1-yl)ethanol (2g)
M. p. 212–214 °C. – FTIR (KBr): 3568, 3100 (OH), 3060 (C–H),
2994 (C–H), 2885, 1601 (Cꢁ=ꢁN) 1585 (Cꢁ=ꢁC), 1481, 1239, 1168,
1057, 872, 725, 701 cm . – H NMR (300 MHz, [D6]DMSO,
TMS): δꢀꢁ=ꢁꢀ3.75 (s, 6H, 2(CH3O), 3.78 (t, 2H, CH2N), 4.20 (t,
−1
1
2H, CH2O), 4.91 (s br, 1H, CH2OH), 7.01–7.81 (m, 13H, Ar-H). 4.4 X-ray structure determinations
–
13C NMR (300 MHz, [D6]DMSO): δꢀꢁ=ꢁꢀ46.8, 55.7, 55.7, 59.7,
111.8, 113.3, 122.1, 123.8, 126.4, 126.7, 128.3, 129.1, 129.4, 129.9, Crystallographic data for 2a, 2c, and 2jare detailed in Table
131.4, 131.5, 134.9, 136.7, 147.9, 148.9, 149.8. – Analysis for 5. Diffraction data for 2a were collected at Baku Estate
C25H25N2O3 (401.5): C 74.79, H 6.28, N 6.98; found C 74.82, University on a Bruker APEXII CCD diffractometer using
H 6.25, N 6.96ꢀ%.
graphite-monochromatized MoK radiation (λꢀꢁ=ꢁꢀ0.71073
Å). Data for 2c and 2j were obtaiαned at the University of
Otago on an Agilent SuperNova (Dual, Cu at zero, Atlas)
diffractometer using a mirror monochromator and CuKα
radiation (λꢀꢁ=ꢁꢀ1.54184 Å). The Bruker data collection was
controlled by Apex2 [60] software with cell refinement
4.3.8 2-(2-(2,5-dimethoxyphenyl)-4,5-diphenyl-1H-
imidazol-1-yl)ethanol (2h)
M. p. 198–200 °C. – FTIR (KBr): 3266 (OH), 3058 (C–H), and data reduction performed using Saint [60]. Multi-
2949 (C–H), 2837 (C–H), 1603 (Cꢁ=ꢁN) 1524 (Cꢁ=ꢁC), 1460, 1230, scan absorption corrections were applied using Sadabs
−1
1
1181, 1056, 803, 727, 698 cm . – H NMR (300 MHz, [D6] [61]. For 2c and 2j these processes were all controlled by
DMSO, TMS): δꢀꢁ=ꢁꢀ3.125 (t, 2H, CH2N), 3.737 (t, 2H, CH2O), CrysAlisPro [62]. The structures were all solved with
3.766 (s, 6H, 2CH3O), 4.716 (s br, 1H, CH2OH), 7.043–7.538 Shelxs [63] and refined by full-matrix least-squares on
(m, 13H, Ar-H) 13C NMR (300 MHz, [D6]DMSO): δꢀꢁ=ꢁꢀ46.7, F2 using Shelxl-2014 [64] and Titan2000 [65]. All non-
56.1, 56.4, 59.8, 113.2, 116.4, 118.0, 121.5, 126.5, 126.5, 128.5, hydrogen atoms were assigned anisotropic displacement
129.3, 129.7, 131.4, 131.6, 135.4, 136.8, 145.0, 151.6, 153.5. parameters. The H atoms of the hydroxyl groups for all
– Analysis for C25H25N2O3 (401.5): C 74.79, H 6.28, N 6.98; three molecules were located in difference Fourier maps
found C 74.75, H 6.25, N 7.00ꢀ%.
and their coordinates refined with atomic displacement
parameters set to 1.5ꢀꢁ×ꢁꢀUeq(O). All other H atoms were posi-
tioned geometrically and refined using a riding model
with d(C–H)ꢀꢁ=ꢁꢀ0.95 Å for aromatic and 0.99 Å for CH2 with
Uisoꢀꢁ=ꢁꢀ1.2ꢀꢁ×ꢁꢀUeq(C) and 0.98 Å, Uisoꢀꢁ=ꢁꢀ1.5ꢀꢁ×ꢁꢀUeq(C) for CH3
atoms. All molecular plots and packing diagrams were
4.3.9 2-(2-(4-(Dimethylamino)phenyl)-4,5-diphenyl-1H-
imidazol-1-yl) ethanol (2i)
M. p. 207–209 oC. – FTIR (KBr): 3320, 3125 (OH), 3064 drawn using Mercury [66]. Other calculations were per-
(C–H), 2970 (C–H), 2890 (C–H), 1670 (Cꢁ=ꢁN) 1579 (Cꢁ=ꢁC), formed using Platon [67] and tabular material was pro-
1450, 1245, 1174, 1098, 874, 724, 694 cm . – 1H NMR duced using WinGX [68].
−1
(300 MHz, [D6]DMSO, TMS): δꢀꢁ=ꢁꢀ3.95 (s, 6H, (CH3)2N), 3.2 (t,
CCDC 1024500 (2a) 1024501 (2b) and 1024505 (2j)
2H, CH2N), 3.95 (t, 2H, CH2O), 4.91 (s, 1H, CH2OH), 6.78–7.65 contain the supplementary crystallographic data for this
(m, 14H, Ar-H), 10 (s br, 1H, C6H4OH). – 13C NMR (300 MHz, paper. These data can be obtained free of charge from the
[D6]DMSO): δꢀꢁ=ꢁꢀ40.1, 46.7, 59.8, 112.2, 118.9, 126.5, 128.4, Cambridge Crystallographic Data Centre via www.ccdc.
129.2, 129.5, 130.2, 131.5, 131.8, 135.4, 136.5, 148.2, 150.8. cam.ac.uk/data_request/cif.
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816ꢀ ꢀS. K. Mohamed et al.: Multicomponent green synthesis, spectroscopic and structural investigation
Table 5:ꢀCrystal data and numbers pertinent to data collection and structure refinement of 2a, 2c, and 2j.
ꢁ
2a
ꢁ
2c
ꢁ
2j
Empirical formula
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
C23H20N2O
40.41
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
C23H20N2O2
356.41
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
C23H19N3O3
385.41
Mr
T, K
296(2)
100(2)
100(2)
Wavelength; λ, Å
MoKα; 0.71073
Monoclinic
P21/n
CuKα; 1.54184
Orthorhombic
Pca21
39.6826(8)
5.6950(12)
7.8390(19)
90
CuKα; 1.54184
Monoclinic
P21/c
Crystal system
Space group
a, Å
b, Å
c, Å
β, deg
V, A3
Z
8.926(2)
14.538(4)
14.401(4)
104.701(4)
1807.7(8)
4
15.36052(11)
8.61192(6)
28.6080(2)
97.1582(7)
3754.88(5)
8
1771.6(6)
4
−3
Dcalcd, g cm
1.251
1.336
1.364
−1
μ, mm
0.077
0.685
0.748
F(000), e
720
752
1616
Crystal size, mm3
θ range, deg
0.18 ꢂ×ꢂ 0.14 ꢂ×ꢂ 0.12 ꢂ
0.21 ꢂ×ꢂ 0.11 ꢂ×ꢂ 0.05ꢂ
0.25 ꢂ×ꢂ 0.16 ꢂ×ꢂ 0.14
3.11–76.80
39758/7843/0.032
7048
2.03–25.49
ꢂ
4.46–76.26
ꢂ
Refl. total/unique/Rint
Refl. obs.with Iꢁꢂ>ꢂꢁ2 σ(I)
Transmission max/min
Data/restraints/ref. param. ꢂ
Goodness-of-fit
Final R1/wR2 [Iꢁꢂ>ꢂꢁ2 σ(I)]
Final R1/wR2 (all data)
Δρfin (max/min), e Å
CCDC reference number
15263/3349/0.053ꢂ
8180/2554/0.031 ꢂ
2543
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
2442
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
0.9908/0.9862
3349/0/238
1.188
1.0000/0.9368
2554/1/250
1.086
1.00000/0.73475
7843/0/529
1.043
0.0347/0.0887
0.0392/0.0925
0.26/–0.26
1024505
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
0.0997/0.2534
0.1204/0.2637
0.37/–0.28
1024500
0.0347/0.0843
0.0375/0.0856
0.21/–0.21
1024501
−3
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Acknowledgments: Authors are gratefully thankful to
Ministry of Higher Education in Egypt for the financial
support of this project in collaboration with National
Academy of Sciences of Azerbaijan under their academic
exchange protocol. Authors also would like to express
their gratitude to the analytical service team (Helen Sut-
ton, Paul Warren and Saeed Gulzar) at Manchester Met-
ropolitan University for providing the spectral results. We
also thank the University of Otago for purchase of the Agi-
lent diffractometer and the Chemistry Department, Uni-
versity of Otago, for support of the work of JS.
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