Catalyst-Free and Green Synthesis of Some Novel Benzamide Derivatives

Article abstract of DOI:10.1002/jhet.2275

In the present work, a simple, green, rapid, and catalyst-free procedure for the synthesis of benzamide derivatives by ring opening of azlactones with diamines such as ethylene diamine and 1,3-propylenediamine is described. The present method offers several advantages such as short reaction times, easy work-up, and mild reaction conditions in the absence of catalyst and any toxic solvent and material. In addition, the structure obtained by X-ray crystallography was compared with the theoretical results obtained by density functional theory using the B3LYP functional and cc-pVDZ basis sets.

Full text of DOI:10.1002/jhet.2275

Month 2014 Catalyst-Free and Green Synthesis of Some Novel Benzamide Derivatives
a
a
a
a
Banafshe Samani Ghaleh Taki, Mahbubeh Rostami, Valiollah Mirkhani, * Majid Moghadam, *
a
a
a
b
Iraj Mohammadpoor-Baltork, Shahram Tangestaninejad, Ahmad Jamali Moghadam, and Reza Kia
a
Catalysis Division, Department of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran
Chemistry Department, Sharif University of Technology, P.O. Box 11155-3516, Tehran, Iran
b
*
E-mail: mirkhani@sci.ui.ac.ir; moghadamm@sci.ui.ac.ir
Received December 26, 2013
DOI 10.1002/jhet.2275
Published online in Wiley Online Library (wileyonlinelibrary.com).
In the present work, a simple, green, rapid, and catalyst-free procedure for the synthesis of benzamide de-
rivatives by ring opening of azlactones with diamines such as ethylene diamine and 1,3-propylenediamine is
described. The present method offers several advantages such as short reaction times, easy work-up, and
mild reaction conditions in the absence of catalyst and any toxic solvent and material. In addition, the struc-
ture obtained by X-ray crystallography was compared with the theoretical results obtained by density func-
tional theory using the B3LYP functional and cc-pVDZ basis sets.
J. Heterocyclic Chem., 00, 00 (2014).
INTRODUCTION
modeling for such applications [16]. In fact, the routes
listed are valuable, but the use of toxic material and sol-
vents, high temperatures, long reaction times, low yields,
and multiple steps for separation could be considered as
disadvantages of these methods.
It is well accepted that amide groups are not only the key
chemical connection of biological systems but are also the
basis for some of the most versatile and widely used syn-
thetic polymers [1]. In addition, anti-retroviral drugs such
as HIV-1 NCp7 inhibitors [2], anti-inflammatory, antipy-
retic, analgesic activities, treatment of atherosclerosis [3],
inhibitors of hepatitis C [4], and inhibitors for targeted mel-
anoma therapy [5] are remarkable properties of these com-
pounds. Amide group is prepared via different methods
such as reaction between primary amine and acyl chloride
Poly(ethylene glycol)s (PEGs) are used as eco-friendly
solvents and can be applied instead of volatile or haloge-
nated organic solvents. These are non-flammable, non-
corrosive, benign, and readily commercially available at
low cost [17]. The PEGs are amphipathic polymers that
are able to dissolve common organic solids [18], and they
present some interesting characteristics, including high
polarity and high boiling point. Moreover, PEGs are stable
to acidic or basic, oxidative or reductive conditions and at
high temperatures (up to 150–250°C). PEGs with low
molecular weight (less than 800 Da) are viscous liquids at
room temperature and can therefore be used as suitable
liquid media [19].
[
6–8], nucleophilic attack to isothiocyanate [9], one-pot
condensation of an aldehyde, acetyl chloride, an enolizable
ketone and acetonitrile [10], condensation of carboxylic
acids with amines in the presence of nanosized sulfated
titania [11], and ring-opening of azlactones with amines
[
12–14]. Recently, primary amides were synthesized
directly from primary alcohols and ammonia using manga-
nese oxide based octahedral molecular sieve (OMS-2) as a
heterogeneous catalyst [15].
These nitrogen-containing compounds play a critical
role in biological applications, and they provide a valuable
Peptides play vital roles in the human body and other
organisms [20]. Because of the good affinity of peptides
toward cells and nucleic acids, the introduction of a peptide
segment to drugs can facilitate their actions to cells and tis-
sues and thereby provide a robust strategy to design new
©
2014 HeteroCorporation

B. Samani Ghaleh Taki, M. Rostami, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork,
S. Tangestaninejad, A. Jamali Moghadam, and R. Kia
Vol 000
drugs or lead compounds. On the other hand, heterocyclic
compounds have distinguished themselves from other
small molecules because of their profound bioactivities.
The practice of ring opening of heterocyclic skeletons with
another amine group into one molecule has received much
attention from synthetic and medicinal chemists for the dis-
covery of novel compounds with unknown or improved
pharmacological properties [21].
Because of the importance of amide compounds, we de-
cided to synthesize a new class of these compounds as potent
drugs by the ring-opening of azlactones with ethylene di-
amine and 1,3-propyldiamine under catalyst-free conditions
using PEG-400 as reaction medium at room temperature
high to excellent yield. It seems that the nature of the sub-
stituents on the aromatic ring has no significant effect on
the reaction yield. Under the same conditions described
for the reaction of ethylene diamine with azlactones, the
reaction of 1,3-diaminopropane was also investigated
(Table 3), and the corresponding amide compounds were
produced in high to excellent yield.
When 1,2-phenylenediamine was used as diamine in the
reaction of compound 1d, the corresponding amide 4d was
produced in 75% yield (Scheme 2).
Scheme 3 shows the proposed mechanism for these reac-
tions. First, diamine reacts with one azlactone molecule 1 to
give the intermediate I, which in turn gives the compounds
II and III. The free amine in compound III reacted with an-
other azlactone molecule 1 to give the intermediate IV, which
is converted to compound V and then to final product 2.
The structures of all compounds were ascertained by
(
Scheme 1). The second aim of this work was the application
of these amides as ligand for coordination with metals.
RESULTS AND DISCUSSION
1
elemental analysis and spectral (IR, UV–vis, H NMR,
13
Synthesis of amide compounds.
First, the reaction
and C NMR) data. Furthermore, the structure of com-
pound 3b was confirmed by X-ray crystallographic analy-
sis (CCDC 908176, Fig. 1). Note that a water molecule is
present in the crystal structure. Also, the crystal packing
of this compound is shown in Figure 2.
conditions were optimized in the reaction of (4Z)-4-(4-
bromobenzylidene)-2-phenyloxazol-5(4H)-one with ethylene
diamine. For choosing the reaction media, the model
reaction was carried out in methanol, ethanol, acetonitrile,
DMF, DMSO, and PEG-400 and also under solvent-free
conditions. As can be seen, the highest yield was obtained at
PEG-400; therefore, all reactions were performed in this
solvent. As mentioned previously, the exact role of PEG-
In the next step, we tried to coordinate these amide com-
pounds as a four-dentate ligand to different metals such as
Mn, Fe, Co, Cu, Zn, Ru, Rh, Pt, and Pd. After several
attempts, no complex was formed, and except for Pd, the
amide ligand was recovered from the reaction mixture. Addi-
400 in this reaction is not clear [22]. Further studies showed
tion of a base such as K CO , NaOH, and NaH and increasing
that a 2:1 ratio of azlactone to ethylene diamine is the best.
Because the model reaction was carried out efficiently at
room temperature, therefore, room temperature was chosen
as reaction temperature. When the model reaction was
carried out at 50°C, the reaction time was reduced to 8 min
2
3
the temperature give no better results. Surprisingly, in the case
of Pd, the amide ligand was cleaved to its azlactone parent.
As shown in Table 4, different amide compounds were
converted to their corresponding azlactones in the presence
(Table 1).
of PdCl
or Pd(OAc) at room temperature. Unfortunately,
2 2
Under the optimized reaction conditions, the reaction
of different azlactone derivatives with ethylene diamine
was carried out under catalyst-free conditions at room tem-
perature. The results, which are summarized in Table 2,
showed that the corresponding amides were obtained in
we could not find any reason for this reaction.
Computational methods.
Density functional theory
(DFT) using the B3LYP functional and cc-pVDZ basis
sets were carried out for geometry optimization and
electronic properties of compound 3b, whereas the
Table 1
Scheme 1
The effect of solvent on the reaction of (4Z)-4-(4-bromobenzylidene)-2-
a
phenyloxazol-5(4H)-one (2g) with ethylene diamine.
b
Entry
Solvent
Time (min)
Yield (%)
1
2
3
4
5
6
7
No solvent
Ethanol
Methanol
Acetonitrile
DMF
12
12
12
12
12
12
12
62
80
75
67
71
82
93
DMSO
PEG-400
a
Reaction conditions: azlactone (2 mmol), ethylene diamine (1 mmol),
solvent (1 mL) at room temperature.
b
Isolated yield.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2014
Synthesis and Application of Heterocycles
electronic transition energies and oscillator strengths were
determined by the TD-DFT/cc-pVDZ level of theory. All
calculations were performed using the Turbomole program
package [23]. The X-ray experimental data were used for
starting geometry in calculations. The optimized geometry
parameters are listed in Table 5 along with experimental
results obtained from X-ray crystallographic study.
parameters to corresponding optimized parameters (Fig. 3),
slight differences are observed. The most important miss
matching is related to the torsion angles C18–C19–N3–
C20, C17–C18–C19–N3 and N3–C20–C21–N4, which
were obtained in this work as ꢀ71.12°, ꢀ66.652°, and
ꢀ138.82, and their experimental values are ꢀ90.6°,
ꢀ85.35° and ꢀ154.3, respectively. The optimized structure
shows the existence of hydrogen bond between the
N―H…O, namely N3―H3 and N2―H2 with O1 and O4
Ground state optimized geometry parameters.
The
optimized structure and the numbering pattern of
compound 3b are represented in Figure 3. From the
structural data in Table 5, comparing the X-ray geometric
Table 3
Synthesis of benzamide derivatives by the reaction of azlactones with 1,3-
Table 2
a
propanediamine.
Synthesis of benzamide derivatives by the reaction of azlactones with
a
ethylene diamine.
b
Entry
1
Ar
Yield (%)
Time (min)
10
b
Entry
1
Ar
Yield (%)
Time (min)
10
92
90
2
3
92
95
15
10
2
3
94
94
15
15
4
5
6
94
94
90
10
8
4
95
10
5
6
7
94
93
88
10
12
20
15
7
90
15
a
Reaction conditions: azlactone (2 mmol) and 1,3-diaminopropane
a
Reaction conditions: azlactone (2 mmol) and ethylene diamine (1 mmol).
Isolated yield.
(1 mmol).
Isolated yield.
b
b
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

B. Samani Ghaleh Taki, M. Rostami, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork,
S. Tangestaninejad, A. Jamali Moghadam, and R. Kia
Vol 000
Scheme 2
atoms, respectively, in which stronger interaction observed
in the view of DFT/cc-pVDZ level of calculation in
comparison with X-ray. The presence of the H-bond shows
an important role in the stabilization of molecular
conformations. The other structural parameters remained
unchanged or showed no considerable change.
Electronic absorption spectra (comparison between theoretical
and experimental results). Simulated absorption spectra in
experimental results are displayed in Figure 4. In order to
obtain the theoretical spectrum, 30 vertically singlet-
excitations were used for calculation. The results are
presented in Table 6. The UV–Vis spectrum of compound
3
b in ethanol (Fig. 4) shows a sharp peak at 330 nm as
λmax and a shoulder at 230 nm. Although theoretical
transition energies have excellent agreement with the
experimental spectrum, it seems the electrostatic solvent
interactions (COSMO model) lead to slightly red-shift
effect on transition energies. Also, that is accompanied
gas and in ethanol using Conductor-like Screening Model
(COSMO) [24–26] were taken and along with its
Scheme 3
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2014
Synthesis and Application of Heterocycles
azlactones in the presence of Pd salts was studied. Finally,
the obtained results by X-ray crystallography were com-
pared with the theoretical results, and a good adaptation
was observed.
EXPERIMENTAL
Chemicals and reagents. All reagents were obtained from
the commercial sources and used as received. FT-IR spectra
were obtained as potassium bromide pellets in the range of
ꢀ
1
4
00–4000 cm
with
a
Nicolet Impact 400D instrument.
JASC1O3 V-670
NMR (400 MHz) and NMR
100 MHz) spectra were recorded on Bruker-Avance 400 using
UV–Vis spectra were recorded on
spectrophotometer.
a
1
H
C
(
6
DMSO-d as solvent. Elemental analysis was carried out on a
LECO, CHNS-932 instrument. Azlactones were prepared
according to published procedure [27].
Figure 1. The crystal structure of compound 3b. [Color figure can be
viewed in the online issue, which is available at wileyonlinelibrary.
com.]
General procedure for preparation of amides. In a 25-mL
round bottom flask, a solution of PEG (PEG-400, 1 mL) and
azlactone (2mmol) was stirred. Then, ethylene diamine or 1,3-
diaminopropane (1mmol) was added to the reaction mixture, and
the mixture was stirred for 30min at room temperature. During
this time, the color of the solution gradually changed to colorless.
The reaction progress was monitored by TLC (petroleum ether/
ethyl acetate: 1/1). After the reaction was completed, distilled
water (5mL) was added. The white precipitates were centrifuged,
dried, and recrystallized from hot ethanol.
with slightly alteration of orbital contributions. Obviously,
the polar solvent mostly affects the orbital energy gaps too.
As shown in Table 7, considering the oscillator strength,
there are several intense electronic transitions. The first one
is a ππ* (H-1 → L) transition, which lies at the 3.75 eV
(
330.93 nm) in gas phase and 3.74 eV (331.93 nm) in sol-
General procedure for reaction of amides with metal salts
vent (Table 7). On the other hand, there are several weak
transitions; among them, S10 (2.95 eV) in gas and S11
of Mn, Fe, Co, Cu, Zn, Ru, Rh, Pt, and Pd.
round bottom flask, a solution of amide (1 mmol) in ethanol
10 mL) was prepared. A solution of metal salt in ethanol (10 mL)
In a 25-mL
(
(4.34 eV) in solvent are more intense than the others. The
was added to this solution, and the reaction mixture was stirred at
room temperature or at 60°C. At the end of the reaction, the
solvent was evaporated to obtain the reaction product.
single-electron excitations that correspond to these two
transitions are H → L + 3 and H-1 → L + 2 in the gas phase
and in solvent, respectively (Fig. 5).
In conclusion, an efficient method for preparation of
amide derivatives by the reaction of diamines with
azlactones under catalyst-free conditions is described.
On the other hand, their conversion to their parent
Supporting information
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(3-oxo-1-
(
thiophen-2-yl)prop-1-ene-3,2-diyl)dibenzamide (2a). mp 153–
ꢀ
1
155°C; IR (KBr): ν (cm ): 3324, 3267, 3067, 2931, 1645, 1527,
1
1473, 1271, 1233, 1209, 716, 626. H NMR (400MHz, DMSO-
Figure 2. The crystal packing of compound 3b. [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com]
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

B. Samani Ghaleh Taki, M. Rostami, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork,
S. Tangestaninejad, A. Jamali Moghadam, and R. Kia
Vol 000
Table 4
Table 5
Cleavage of amide compounds to azlactones in the presence of palladium
Experimental and optimized structural parameter results.
a
salts.
DFT
Parameters
cc-pVDZ
Experimental
Bond lengths (Å)
1.397
1.398
1.400
1.395
1.404
1.405
1.500
1.231
1.374
1.407
1.517
1.228
1.360
1.459
1.535
1.540
1.460
1.355
1.229
1.518
1.408
1.375
1.231
1.501
1.405
1.397
1.398
1.400
1.395
1.404
1.408
1.353
1.469
1.424
1.398
1.395
1.400
1.400
1.424
1.365
1.419
1.354
1.470
1.407
1.398
1.395
1.400
1.400
1.364
1.419
1.423
1.944
2.027
C1–C2
C2–C3
C3–C4
C4–C5
C5–C6
C6–C1
C6–C7
C7–O1
1.381(5)
1.374(6)
1.376(6)
1.372(5)
1.387(5)
1.383(5)
1.501(4)
1.222(4)
1.350(4)
1.441(5)
1.461(6)
1.246(4)
1.358(4)
1.472(5)
1.510(6)
1.549(5)
1.447(5)
1.310(5)
1.258(4)
1.495(5)
1.423(4)
1.365(4)
1.206(5)
1.493(6)
1.337(6)
1.444(6)
1.355(6)
1.350(7)
1.376(6)
1.387(5)
1.423(4)
1.339(4)
1.464(5)
1.374(6)
1.375(6)
1.370(7)
1.365(7)
1.396(6)
1.422(5)
1.369(5)
1.425(4)
1.340(5)
1.449(6)
1.398(6)
1.379(7)
1.347(7)
1.378(7)
1.387(6)
1.374(5)
1.413(6)
1.386(6)
2.084
b
Entry
1
Product
Yield (%)
92
Time (min)
10
C7–N1
N1–C8
C8–C16
C16–O2
C16–N2
N2–C17
C17–C18
C18–C19
C19–N3
N3–C20
C20–O3
C20–C21
C21–N4
N4–C22
C22–O4
C22–C23
C23–C28
C28–C27
C27–C26
C26–C25
C25–C24
C24–C23
N4–C21
C21–C29
C29–C30
C30–C31
C31–C32
C32–C33
C33–C34
C34–C35
C35–C30
C35–O6
O6–C37
C8–C9
2
90
10
3
4
93
87
5
12
5
90
8
C9–C10
C10–C11
C11–C12
C12–C13
C13–C14
C14–C15
C15–O5
O5–C36
C15–C10
O1–H3B
O4–H2B
a
Reaction conditions: amide compound (1 mmol), Pd salt (1 mmol), and
EtOH (20 mL).
Isolated yield.
b
d6), δ: 9.80 (s, 2H, N―H Benzamide), 8.28 (s, 2H, N―H amide),
4.430
8
7
3
3
1
4
9
.09 (d, J = 7.2 Hz), 7.66 (s, H-benzyl), 7.61–7.64 (m, 2H), 7.52–
Bond angles (°)
113.963
116.023
113.867
120.357
1
2
.59 (m, 4H), 7.39 (d, J = 2.8 Hz), 7.1 (dd, J = 5.2, J = 3.6 Hz),
N2–C17–C18
C17–C18–C19
C18–C19–N3
C19–N3–C20
113.5(4)
113.7(3)
114.1(3)
122.1(3)
1
3
.38 (s, 4H, CH
2
―CH
2
). C NMR (100 MHz, DMSO-d
6
), δ:
9.0, 125.6, 126.6, 126.8, 128.1, 128.2, 130.2, 131.6, 132.2,
33.9, 135.7, 164.7, 165.0. C H N O S Calcd: C, 63.14%; H,
3
0 26 4 4 2
.59%; N, 9.82%; S, 11.24%; Found: C, 63.09%; H, 4.62%; N,
.78%, S, 11.20%. UV–vis (λmax, nm): 319.
(
Continued)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2014
Synthesis and Application of Heterocycles
Table 5
(Continued)
DFT
Parameters
cc-pVDZ
Experimental
N3–C20–O3
C20–C21–N4
C21–C22–N4
N4–C21–C29
C29–C30–C31
C30–C31–C32
C32–C33–C34
C34–C35–C30
C34–C35–O6
C35–O6–C37
N4–C22–O4
O4–C22–C23
C22–C23–C28
C23–C28–C27
C28–C27–C26
C27–C26–C25
C26–C25–C24
C24–C23–C28
C17–N2–C16
N2–C16–O2
O2–C16–C8
C8–N1–C7
N1–C7–O1
C7–C6–C1
C1–C2–C3
C2–C3–C4
C3–C4–C5
C4–C5–C6
C8–C9–C10
C9–C10–C11
C9–C10–C15
C10–C15–C14
C15–C14–C13
C13–C12–C11
C11–C10–C15
C15–O5–C36
124.43
121.6(4)
114.2(3)
120.2(3)
121.3(4)
125.2(3)
123.5(4)
121.6(3)
121.4(4)
123.8(4)
117.9(4)
122.1(4)
121.5(3)
123.8(4)
120.7(4)
117.7(5)
121.2(5)
121.1(5)
119.8(4)
124(4)
121.4(4)
123.2(3)
118.7(3)
122.2(3)
123.1(4)
119.8(4)
121(3)
113.971
124.032
123.799
124.007
121.924
120.221
120.775
123.707
118.88
122.663
121.456
123.071
120.297
120.076
119.884
120.105
120.367
121.061
124.905
119.991
115.081
122.774
117.657
120.328
120.122
119.885
120.081
128.39
Figure 3. Optimized structure and their atom numbering of the title com-
pound (hydrogen atoms clearly omitted except for hydrogen bonding).
Color figure can be viewed in the online issue, which is available at
[
wileyonlinelibrary.com.]
118.8(4)
121.3(4)
130.1(3)
122.8(4)
121.1(4)
122.1(4)
118.8(5)
119.3(5)
116(4)
123.692
118.686
120.718
120.038
119.552
117.565
118.858
118.4(4)
Dihedral angles (°)
ꢀ71.12
N3–C19–C18–C17
C18–C19–N3–C20
C19–N3–C20–O3
C20–C21–C29–C30
N3–C20–C21–N4
N2–C16–C8–C9
C16–C8–C9–10
ꢀ90.6(5)
ꢀ85.35(4)
4.2(5)
173.3(4)
ꢀ154.3(3)
44.7(6)
177.2(4)
ꢀ139.7(4)
56.6(5)
ꢀ66.652
ꢀ7.08
176.11
ꢀ138.82
46.59
175.20
Figure 4. The experimental spectra of title compound with vertical exci-
tation in gas phase (black lines) and in solvent (blue lines). [Color figure
can be viewed in the online issue, which is available at
wileyonlinelibrary.com]
C9–C8–N1–C7
C19–C18–C17–N2
ꢀ146.84
58.41
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(1-(2-
methoxyphenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (2b). mp
69.89%; H, 5.54%; N, 9.06%; Found: C, 69.86%; H, 5.55%; N,
9.04%. UV–vis (λmax, nm): 321.
ꢀ
1
2
2
28–230°C; IR (KBr): ν (cm ): 3393, 3343, 3285, 3239, 3063,
838, 1648, 1617, 1577, 1519, 1480, 1253, 1021, 755, 706. H
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(1-(4-
1
methoxyphenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (2c). mp
ꢀ
1
6
NMR (400 MHz, DMSO-d ), δ: 9.80 (s, 2H, N―H Benzamide),
137–140°C; IR (KBr): ν (cm ): 3371, 3296, 3057, 2940,
8
.25 (s, 2H, N―H amide), 7.42–7.56 (m, 10H), 7.28 (td, 2H,
2840, 1647, 1609, 1577, 1536, 1508, 1473, 1258, 1207, 1176,
1
2
1
J = 15.6, J = 1.2 Hz), 7.04 (d, 2H, J = 8.0 Hz), 6.84 (t,
1024, 835, 704. H NMR (400 MHz, DMSO-d
), δ: 9.87 (s, 2H,
6
J = 7.6 Hz, 2H, Benzilic), 3.83 (s, 6H, O―CH ), 3.3 (s, 4H,
N―H Benzamide), 8.21 (s, 2H, N―H amide), 8.02 (d, 4H,
J = 7.2Hz), 7.58 (t, J = 7.6 Hz), 7.48–7.51 (8H, m), 7.20 (s, 2H,
3
1
3
CH ―CH ). C NMR (100 MHz, DMSO-d ), δ: 24.4, 55.4,
2
2
6
1
11.1, 120.1, 123.9, 123.9, 127.9, 128.1, 128.5, 130.0, 131.4,
Benzilic), 6.90 (d, 4 Hz, J = 9.2 Hz), 3.74 (s, 6H, OCH
3
), 3.29
(s, 4H). C NMR (100 MHz, DMSO-d ), δ: 41.1, 55.1, 113.9,
6
1
3
1
33.8, 157.1, 165.3, 165.9, 174.3. C36 Calcd: C,
H
34
N
4
O
6
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

B. Samani Ghaleh Taki, M. Rostami, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork,
S. Tangestaninejad, A. Jamali Moghadam, and R. Kia
Vol 000
Table 6
The calculated singlet excited states.
Gas
Solvent
State
Energy (eV)
Wavelength (nm)
Oscillator strength
Energy (eV)
Wavelength (nm)
Oscillator strength
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
S
1
3.62
3.67
3.75
3.78
3.82
3.85
4.06
4.09
4.15
4.24
4.28
4.31
4.34
4.40
4.41
4.44
4.45
4.48
4.49
4.51
4.55
4.56
4.62
4.64
4.65
4.65
4.67
4.67
4.78
4.81
342.86
337.62
330.93
327.99
324.54
321.95
305.31
303.15
298.40
292.47
289.37
287.65
285.88
281.74
280.92
279.17
278.77
276.98
276.28
274.98
272.39
271.95
268.20
267.23
266.82
266.67
265.51
265.30
259.57
257.66
0.050
0.115
0.195
0.167
0.047
0.010
0.020
0.007
0.024
0.147
0.034
0.000
0.008
0.005
0.008
0.023
0.064
0.047
0.017
0.006
0.035
0.007
0.006
0.007
0.004
0.007
0.001
0.004
0.000
0.000
3.62
3.68
3.74
3.79
4.17
4.21
4.22
4.26
4.28
4.30
4.34
4.37
4.42
4.46
4.56
4.59
4.63
4.65
4.78
4.79
4.80
4.83
4.85
4.88
4.88
4.91
4.91
4.92
4.96
4.98
342.76
336.90
331.93
327.42
297.32
294.66
293.65
291.18
289.75
288.64
285.35
283.76
280.50
278.08
271.73
270.28
267.89
266.72
259.52
258.79
258.26
256.53
255.80
254.22
254.14
252.64
252.39
252.00
249.87
249.02
0.084
0.231
0.355
0.110
0.014
0.009
0.063
0.015
0.028
0.063
0.147
0.027
0.013
0.012
0.041
0.040
0.035
0.020
0.003
0.002
0.012
0.015
0.009
0.016
0.008
0.007
0.002
0.001
0.005
0.003
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
Table 7
Calculated vertical transition energies at TD-DFT/cc-pVDZ level of theory on the optimized equilibrium geometry in gas phase and in solvent along with
experimental results.
Experimental
TD-DFT/cc-pVDZ
TD-DFT/cc-pVDZ/COSMO
Wavelength
(nm)
Wavelength
(nm)
Oscillator
strength
Wavelength
Oscillator
strength
Orbital
contribution
State
Abs.
(nm)
S
S
S
3
330
230
—
2.00
0.15
—
331
292.5
289.37
0.20
0.15
0.034
331.9
288.64
285.4
0.35
0.063
0.15
H-1 → L
H → H + 3
H-1 → L + 2
10
11
1
3
1
1
6
9
26.6, 126.7, 127.7, 127.9, 128.2, 128.3, 128.8, 129.3, 131.0,
31.6, 133.7, 159.5, 165.5, 165.8. C36 Calcd: C,
9.89%; H, 5.54%; N, 9.06%; Found: C, 69.86%; H, 5.56%; N,
.08%. UV–vis (λmax, nm): 320.
(s, 2H, Benzilic), 3.34 (4H, CH
DMSO-d ), δ: 18.5, 56.0, 127.9, 128.2, 128.5, 130.6, 132.9,
165.2. C H Cl N O Calcd: C, 65.08%; H, 4.50%; N,
2 2
―CH ). C NMR (100 MHz,
H
34
N
4
O
6
6
3
4
28
2 4 4
8.93%; Found: C, 65.05%; H, 4.52%; N, 8.89%. UV–vis
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(1-(4-
(λmax, nm): 318.
chlorophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (2d). mp
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(1-(2,4-
dichlorophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (2e). mp
128–130°C (decomp.); IR (KBr): ν (cm ): 3302, 3285, 3065,
ꢀ
1
1
2
38–140°C (decomp.); IR (KBr): ν (cm ): 3365, 3266, 3067,
1
ꢀ1
963, 2874, 1654, 1609, 1543, 1483, 1280, 1091, 711.
H
NMR (400 MHz, DMSO-d6), δ: 9.96 (s, 2H, N―H
Benzamide), 8.31 (s, 2H, N―H amide), 7.97 (d, 4H,
J = 11.6 Hz), 7.46–7.59 (m, 10H), 7.41 (d, 4H, J = 8.8 Hz), 7.16
2941, 2839.67, 1648, 1609.30, 1582, 1521, 1469, 1278, 1101,
1
6
1052, 868, 693. H NMR (400 MHz, DMSO-d ), δ: 9.92 (s, 2H,
N―H Benzamide), 8.40 (t, J= 5.2 Hz, 2H, N―H amide), 7.91 (d,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2014
Synthesis and Application of Heterocycles
(
(
(
(
(
(
400 MHz, DMSO-d ), δ: 9.83 (s, 2H, N―H Benzamide), 8.17
t, 2H, J = 6.0 Hz, N―H amide), 8.09 (d, 4H, J = 7.2 Hz), 7.65
6
s, 2H), 7.59–7.63 (m, 4H), 7.52–7.56 (t, 4H, J = 7.2 Hz), 7.41
1
2
d, 2H, J = 3.2 Hz), 7.09 (dd, 2H, J = 4.2, J = 3.6 Hz), 3.37
13
s, 4H, CH
2 2
―N), 1.60 (m, 2H, C―CH ―C). C NMR
100 MHz, DMSO-d ), δ: 29.4, 36.52, 125.2, 126.9, 127.0, 128.2,
6
1
28.3, 130.8, 131.7, 133.0, 133.9, 137.0, 164.9, 166.1.
Calcd: C, 63.68%; H, 4.83%; N, 9.58%; S,
0.97%; Found: C, 63.66%; H, 4.81%; N, 9.60%, S, 10.93%.
31 28 4 4 2
C H N O S
1
UV–vis (λmax, nm): 325.
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(1-(2-
methoxyphenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (3b). mp
ꢀ
1
1
2
13–115°C; IR (KBr): ν (cm ): 3408, 3314, 3253, 3067,
1
935, 2840, 1649, 1578, 1517, 1479, 1252, 1020, 755, 711. H
NMR (400MHz, DMSO-d ), δ: 9.84 (s, 2H, N―H Benzamide),
6
8
7
7
.18 (t, J = 5.6 Hz, 2H, N―H amide), 7.96 (d, 2H, J = 7.2 Hz),
.55 (t, 2H, J = 7.2 Hz), 7.47 (t, 6H, J = 7.6 Hz), 7.41 (s, 2H),
1
2
.28 (td, 2H, J = 8, J = 1.6 Hz), 7.04 (d, 2H, J = 8.4 Hz), 6.84
), 3.22 (d, J = 6.0 Hz,
(
t, 2H, J = 7.2 Hz), 3.83 (s, 6H, O―CH
3
Figure 5. Representation of the molecular orbitals corresponding to the
1
3
4
H, CH ―N), 1.63 (t, 2H, J = 6.4 Hz, C―CH ―C). C NMR
one-electron excitation involved in the transition calculated for S
3
and
2
2
S
10 in gas (solid line) and S and S11 in the presence of solvent (dashed
3
(100 MHz, DMSO-d ), δ: 29.3, 36.4, 55.5, 56.0, 111.1, 120.1,
6
line). [Color figure can be viewed in the online issue, which is available
122.9, 123.7, 127.4, 128.0, 128.1, 128.5, 130.0, 131.5, 138.0,
at wileyonlinelibrary.com.]
157.1, 165.0, 166.1. C37
36 4 6
H N O Calcd: C, 70.24%; H, 5.74%;
N, 8.86%; Found: C, 70.25%; H, 5.72%; N, 8.85%. UV–vis
(
λmax, nm): 328.
4
H, J= 7.2 Hz), 7.75 (d, 2H, J= 2.4 Hz), 7.45–7.58 (m, 6H), 7.37 (dd,
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(1-(4-
1
2
2H, J=8.6, J= 2.4 Hz), 7.17 (s, 2H, Benzilic), 3.30 (s, CH ―CH ).
methoxyphenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (3c). mp
2
2
13
ꢀ1
6
C NMR (400 MHz, DMSO-d ), δ: 18.5, 56.0, 122.7, 127.3, 127.4,
120–121°C (decomp.); IR (KBr): ν (cm ): 3360, 3278, 3067,
1
1
5
8
27.7, 127.9, 128.2, 128.5, 128.9, 130.6, 131.2, 131.7, 132.0, 132.9,
2935, 2837, 1649, 1602, 1577, 1512, 1477, 1253, 1176, 1029,
1
33.2, 133.3, 134.0, 164.7, 165.8. C H Cl N O Calcd: C,
828, 704. H NMR (400 MHz, DMSO-d
6
), δ: 9.92 (s, 2H,
34
26
4 4 4
8.64%; H, 3.76%; N, 8.05%; Found: C, 58.61%; H, 3.78%; N,
.02%. UV–vis (λmax, nm): 315.
N―H Benzamide), 8.18 (t, 2H, J = 6.0 Hz, N―H amide), 8.03
(d, 4H, J = 7.6 Hz), 7.50–7.60 (m, 10H), 7.20 (s, 2H, Benzilic),
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(1-(4-
6.91 (d, 4H, J = 8.8 Hz), 3.74 (s, 6H, OCH
J = 6.0 Hz, CH ―N), 1.57 (m, 2H, C―CH ―C). C NMR
(100 MHz, DMSO-d ), δ: 25.3, 37.0, 55.1, 114.0, 126.7, 126.8,
127.9, 128.0, 128.2, 128.3, 129.0, 131.0, 131.5, 133.8, 159.5,
159.5, 165.0, 165.2, 165.9. C37 Calcd: C, 70.24%; H,
3
), 3.21 (d, 4H,
1
3
bromophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (2f).
33–135°C (decomp.); IR (KBr): ν (cm ): 3373, 3271, 3060,
mp
2
2
ꢀ
1
1
6
2
961, 22880, 1651, 1581, 1508, 1481, 1279, 1074, 1009, 710.
1
H NMR (400 MHz, DMSO-d
6
), δ: 10.02 (s, 2H, N―H
36 4 6
H N O
Benzamide), 8.37 (s, 2H, N―H amide), 7.99 (d, 4H,
5.74%; N, 8.86%; Found: C, 70.25%; H, 5.72%; N, 8.86%.
UV–vis (λmax, nm): 318.
J = 7.2 Hz), 7.45–7.59 (m, 10H), 7.14 (s, 2H, C¼C alkene),
1
3
3
4
1
1
.25 (s, 4H, CH ―CH ). C NMR (100 MHz, DMSO-d ), δ:
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(1-(4-
2
2
6
1.0, 121.5, 121.6, 126.9, 127.3, 127.4, 127.9, 128.2, 128.3,
29.0, 130.9, 131.1, 131.4, 131.7, 133.5, 133.6, 133.7, 165.2,
chlorophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (3d). mp
ꢀ
1
148–150°C (decomp.); IR (KBr): ν (cm ): 3422, 3278, 3064,
1
65.7, 173.0. C34
H
28Br
2
N
4
O
4
Calcd: C, 57.00%; H, 3.94%;
2938, 1654, 1579, 1521, 1478, 1284, 1093, 1013, 706. H NMR
N, 7.82%; Found: C, 57.02%; H, 3.95%; N, 7.80%. UV–vis
(400 MHz, DMSO-d ), δ: 9.97 (s, 2H, N―H Benzamide), 8.25
6
(
λmax, nm): 312.
(s, 2H), 7.98 (d, 4H, J = 6.8), 7.48–7.60 (m, 10H), 7.41 (d, 4H,
J = 6.8Hz), 7.14 (s, 2H, Benzilic), 3.22 (d, 4H, J = 5.6 Hz), 1.64
N,N′-(1E,1′E)-3,3′-(Ethane-1,2-diylbis(azanediyl))bis(1-(4-
13
nitrophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (2g). mp
1
2
(m, 2H, C―CH
36.5, 127.1, 127.4, 127.9, 128.2, 128.3, 128.5, 130.1, 131.0,
131.7, 132.8, 133.3, 133.5, 164.9, 165.9. C35 Calcd:
2 6
―C). C NMR (100MHz, DMSO-d ), δ: 29.1,
ꢀ
1
52–155°C; IR (KBr): ν (cm ): 3445, 3332, 3230, 3068, 2928,
875, 1646, 1597, 1509, 1478, 1342, 1281, 1110, 711. H NMR
1
H30Cl N O
2 4 4
(
(
400MHz, DMSO-d ), δ: 10.14 (s, 2H, N―H Benzamide), 8.47
s, 2H, N―H amide), 8.19 (d, 4H, J = 8.8 Hz), 7.96 (d, 4H,
C, 65.53%; H, 4.71%; N, 8.73%; Found: C, 65.54%; H, 4.69%;
N, 8.70%. UV–vis (λmax, nm): 320.
6
J = 7.6 Hz), 7.75 (d, 4H, J = 8.8 Hz), 7.58 (t, 2H, J = 7.2 Hz), 7.48
t, 4H, J = 7.6Hz), 7.18 (s, 2H, Benzilic), 3.35 (s, 4H,
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(1-(2,4-
(
dichlorophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (3e). mp
13
ꢀ1
CH ―CH ). C NMR (100 MHz, DMSO-d ), δ: 21.1, 123.6,
76–78°C (decomp.); IR (KBr): ν (cm ): 3378, 3260, 2935.13,
2
2
6
1
1
25.2, 128.0, 128.3, 130.0, 131.8, 133.3, 133.6, 141.5, 146.4,
2836.77, 1649.80, 1602.56, 1576.52, 1511.92, 1477.21, 1253.50,
1
65.0, 165.8, 172.0. C34 Calcd: C, 62.96%; H, 4.35%;
H N O
28 6 8
1176.36, 1028.84, 703.89. H NMR (400 MHz, DMSO-d
6
), δ: 9.93
N, 12.96%; Found: C, 62.98%; H, 4.38%; N, 12.93%. UV–vis
(s, 2H, N―H Benzamide), 8.35 (t, 2H, J=6.0Hz, N―H amide),
7.91 (d, 4H, J= 7.2 Hz), 7.69 (d, 2H, J=1.2Hz), 7.45–7.58 (m,
(λmax, nm): 335, 358.
1
2
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(3-oxo-
10H), 7.37 (dd, 2H, J=8.6, J= 2.4 Hz), 7.16 (s, 2H, Benzilic),
13
1
1
1
-(thiophen-2-yl)prop-1-ene-3,2- diyl)dibenzamide (3a).
mp
3.26 (s, 4H, H
(100 MHz, DMSO-d
127.6, 127.7, 127.9, 128.2, 128.5, 128.9, 129.1, 129.9, 130.6,
2
C―N), 1.67 (m, 2H, C―CH
2
―C). C NMR
ꢀ
1
60–164°C; IR (KBr): ν (cm ): 3349, 3250, 3067, 2925, 1650,
6
), δ: 29.0, 36.6, 122.7, 126.0, 127.3, 127.4,
1
621, 1526, 1466, 1271, 1282, 1210, 701, 642. H NMR
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

B. Samani Ghaleh Taki, M. Rostami, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork,
S. Tangestaninejad, A. Jamali Moghadam, and R. Kia
Vol 000
1
1
31.0, 131.2, 131.7, 132.0, 133.1, 133.2, 133.4, 134.2, 164.4,
65.9. C H Cl N O Calcd: C, 59.17%; H, 3.97%; N, 7.89%;
REFERENCES AND NOTES
35
28
4 4 4
[
[
1] Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471.
2] Goel, A.; Mazur, S. J.; Fattah, R. J.; Hartman, T. L.; Turpin,
J. A.; Huang, M.; Rice, W. G.; Appella, E.; Inman, J. K. Bioorg Med
Chem Lett 2002, 12, 767.
Found: C, 59.19%; H, 3.95%; N, 7.88%. UV–vis (λmax, nm): 317.
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(1-(4-
bromophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (3f).
1
1
mp
ꢀ
1
54–156°C; IR (KBr): ν (cm ): 3422, 3276, 3062, 2936, 1654,
[
[
3] Singha, N. C.; Sathyanarayana, D. N. J Mol Struct 1997, 403, 123.
4] Cheng, C. C.; Shipps, G. W.; Yang, I. Z.; Kawahata, N.;
1
581, 1519, 1472, 1274, 1074, 1009, 704. H NMR (400 MHz,
DMSO-d
6
), δ: 9.96 (s, 2H, N―H Benzamide), 8.25 (t, 2H,
Lesburg, C. A.; Duca, J. S.; Bandouveres, J.; Bracken, J. D.; Jiang, C. K.;
Agrawal, S.; Ferrari, E.; Huang, H.-C. Bioorg Med Chem Lett 2010,
J = 6.0 Hz, N―H amide), 7.98 (d, 4H, J = 7.6 Hz), 7.46–7.60 (m,
2
0, 2119.
1
1
1
1
4H), 7.11 (s, 2H, Benzilic), 3.22 (d, 4H, J = 6.4 Hz, CH ―CH ),
.64 (m, 2H). C NMR (100 MHz, DMSO-d ), δ: 29.0, 41.5,
19.6, 119.9, 121.6, 126.6, 127.7, 128.7, 130.3, 130.7, 131.7,
32.6, 133.6, 134.2, 135.1, 135.4, 164.9, 165.9, 167.8, 173.8.
2 2
13
[5] Vivier, M.; Rapp, M.; Galmier, M.-J.; Jarrousse, A.-S.; Miot-
Noirault, E.; Leal, F.; Weber, V.; Métin, J.; Sauzière, J.; Chezal, J.-M.;
Madelmont, J.-C. Eur J Med Chem 2011, 46, 5705.
6
[6] Seeback, D.; Beck, A. K.; Imwinkelried, R.; Roggo, S.;
35
C H30Br
N O
2 4 4
Calcd: C, 57.55%; H, 4.14%; N, 7.67%; Found:
Wonnacott, A. Helv Chim Acta 1987, 70, 954.
C, 57.53%; H, 4.16%; N, 7.70%. UV–vis (λmax, nm): 325.
N,N′-(1E,1′E)-3,3′-(Propane-1,3-diylbis(azanediyl))bis(1-(4-
[7] Martinho, M.; Banse, F.; Sainton, J.; Philouze, C.; Guillot, R.;
Blain, G.; Dorlet, P.; Lecomte, S.; Girerd, J. Inorg Chem 2007, 46, 1709.
[8] Leitch, D. C.; Schafer, L. L. Organomet 2010, 29, 5162.
nitrophenyl)-3-oxoprop-1-ene-3,2-diyl)dibenzamide (3g).
mp
ꢀ
1
[9] Ahmed, I. T. Phosphorus Sulfur Silicon 2006, 181, 267.
2
37–239°C; IR (KBr): ν (cm ): 3438, 3414, 3234, 3066,
[10] Bhatia, B.; Reddy, M. M.; Iqbal, J. J Chem Soc Chem
2
937, 2871, 1653, 1598, 1518, 1474, 1343, 1278, 1110, 691.
Commun 1994, 713.
1
H NMR (400 MHz, DMSO-d ), δ: 10.13 (s, 2H, N―H
6
[11] Hosseini-Sarvari, M.; Sodagar, E.; Doroodmand, M. M. J Org
Benzamide), 8.38 (t, 2H, J = 5.6 Hz, N―H amide), 8.19 (d,
Chem 2011, 76, 2853.
4
H, J = 8.8 Hz), 7.97 (d, 4H, J = 7.2 Hz), 7.76 (d, 4H,
J = 8.8 Hz), 7.57 (t, 2H, J = 7.6 Hz), 7.50 (t, 4H, J = 7.6 Hz),
.17 (s, 2H,1 Benzilic), 2.88 (m, 4H), 1.68 (m, 2H,
[12] Shi, F.; Dai, A.-X.; Zhang, X.-H.; Jiang, B. S.; Tu, J. ACS
Comb Sci 2011, 13, 147.
[13] Rajitha, G. K.; Prasad, V. S. R. G.; Bharathi, K. Asian J Chem
2010, 22, 1197.
7
3
C―CH ―C). C NMR (100 MHz, DMSO-d ), δ: 28.9, 36.5,
2
6
[
14] Andersen, K. K.; Gloster, D. F.; Bray, D. D.; Shoja, M.; Kjær, A.
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3
1
1
6.6, 123.5, 127.8, 128.0, 128.2, 130.0, 131.6, 141.8, 146.2,
64.9, 165.9. C35 Calcd: C, 63.44%; H, 4.56%; N,
2.68%; Found: C, 63.47%; H, 4.55%; N, 12.69%. UV–vis
30 6 8
H N O
[
(
λmax, nm): 323.
[16]
Gupta, R. R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry;
N,N′-((1E,1′E)-(1,2-Phenylenebis(azanediyl))bis(1-(4-
Springer Verlag; Berlin Heidelberg-Germany, 1998; p 1.
[17] Bailey Jr., F. E.; Koleske, J. V. Poly(ethylene oxide);
Academic Press; New York, 1976.
chlorophenyl)-3-oxoprop-1-ene-3,2-diyl))dibenzamide (4d). mp
ꢀ
1
1
2
8
38–140°C (decomp.); IR (KBr): ν (cm ): 3360, 3281, 3062,
[18] Heldebrant, D. J.; Jessop, P. G. J Am Chem Soc 2003, 125, 5600.
935, 2837, 1651, 1602, 1577, 1512, 1477, 1253, 1176, 1029,
1
[19] Colacino, E.; Martinez, J.; Lamaty, F.; Patrikeeva, L. S.;
Khemchyan, L. L.; Ananikov, V. P.; Beletskaya, I. P. Coord Chem Rev
28, 704. H NMR (400 MHz, DMSO-d ), δ: 9.92 (s, 2H, N―H
6
Benzamide), 8.25 (d, 2H, J = 7.6 Hz), 8.18 (t, 2H, J = 6.0Hz,
N―H amide), 8.03 (d, 4H, J = 7.6Hz), 7.50–7.60 (m, 10H), 7.20
2012, 256, 2893.
[20] Tian, F.-F.; Zhou, P.; Li, Z.-L. J Mol Struct 2007, 830, 106.
(
3
(
1
s, 2H, Benzilic), 7.07 (d, 2H, J = 7.5Hz), 6.91 (d, 4H, J = 8.8 Hz),
.74 (s, 6H, OCH ), 3.21 (d, 4H, J = 6.0 Hz, CH ―N), 1.57
m, 2H, C―CH ―C). C NMR (100MHz, DMSO-d ), δ: 114.0,
24.5, 124.8, 126.7, 126.8, 127.9, 128.0, 128.2, 128.3, 129.0,
31.0, 131.5, 133.8, 159.5, 159.5, 165.0, 165.2, 165.9.
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[23] Turbomole, G. H. A development of the University of Karlsruhe
3
2
1
3
2
6
and Forschungazentrum Karlsruhe GmbH. 1989–2007, since 2007;
Turbomole V6.3, available from http://www.turbomole.com
1
[
[
24] Baldridge, K.; Klamt, A. J Chem Phys 1997, 106, 6622.
25] Klamt, A.; Schuurmann, G. J Chem Soc Perkin Trans 1993,
38 2 4 4
C H28Cl N O Calcd: C, 67.56%; H, 4.18%; N, 8.29%; Found:
C, 67.55%; H, 4.20%; N, 8.29%.
2
, 799.
26] Schafer, A.; Klamt, A.; Sattel, D.; Lohrenz, J. C. W.; Eckert, F.
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[
[
Acknowledgment. The support of this work by the Research
Council of the University of Isfahan is acknowledged.
Tangestaninejad, S.; Mohammadpoor-Baltork, I. Appl Catal A: Gen 2011,
397, 27.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet