Synthesis and crystal structures of novel (4-phenylthiazol-2(3H)-ylidene) benzamide and ((benzoylimino)-3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)acetate derivatives

Article abstract of DOI:10.1002/hc.21409

A new approach to the synthesis of new heterocyclic compounds with benzoylisothiocyanate, amines, and 2-bromoacetophenone (phenacyl bromide) fragments in one molecule has been developed. The synthesis method comprises condensation reaction for the prepara

Full text of DOI:10.1002/hc.21409

Received: 5 July 2017
DOI: 10.1002/hc.21409
Revised: 14 December 2017
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R E S E A R C H A R T I C L E
Synthesis and crystal structures of novel (4-phenylthiazol-
2(3H)-ylidene) benzamide and ((benzoylimino)-3-(9,10-dioxo-
9,10-dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)acetate
derivatives
Mahshid Hossaini1
Majid Kolahdoozan2
Reza Heydari1
Claudia Graiff3
Malek Taher Maghsoodlou1
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1Department of Chemistry, The University
of Sistan and Baluchestan, Zahedan, Iran
2Department of Chemistry, Shahreza
Branch, Islamic Azad University, Shahreza,
Isfahan, Iran
3Department of Chemistry, Life Sciences
and Environmental Sustainability,
University of Parma, Parma, Italy
Abstract
A new approach to the synthesis of new heterocyclic compounds with benzoyliso-
thiocyanate, amines, and 2-bromoacetophenone (phenacyl bromide) fragments in
one molecule has been developed. The synthesis method comprises condensation
reaction for the preparation of novel (4-phenylthiazol-2(3H)-ylidene) benzamide de-
rivatives. These new compounds were synthesized via one-pot and multicomponent
reaction of 2-furanmethylamine, 5-chloro-2-phenoxyaniline, and 1-naphthylamine
with phenacyl bromide and substituted benzoylisothiocyanates. Moreover, new se-
ries of anthraquinone-thiazole hybrids have been synthesized. These compounds
were prepared from unsymmetrical thiourea containing anthraquinone and dialkyl
acetylenedicarboxylate. The nature of the compounds was confirmed by IR, 1HNMR,
13CNMR, mass spectrometry, and CHNS elemental analysis. The structural elucida-
tion was accomplished by single-crystal X-ray diffraction methods.
Correspondence
Reza Heydari, Department of Chemistry,
The University of Sistan and Baluchestan,
Zahedan, Iran.
Email: heydari@chem.usb.ac.ir
and anti-HIV[8] antischistosomal[9] activity. Various methods
for the synthesis of thiazole have been developed. A general
1
INTRODUCTION
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Heterocyclic chemistry has constituted one of the largest areas
of research in organic chemistry. A large number of natural
products, such as vitamins, hormones, antibiotics, alkaloids,
are constituted of heterocyclic compounds. Furthermore,
most drugs are based on heterocyclic molecules. They have
also contributed to industrial development and to the im-
provement in the quality of life through their applications as
herbicide, agrochemicals, dyes, plastics, food additives, cos-
metics, and so on.[1]
Heterocyclic compounds containing nitrogen and sulfur
specifically thiazoles and their derivatives are core struc-
ture in synthetic intermediates and common substructure in
numerous biologically active compounds that are known to
exhibit significant biological activities such as anticancer,[2]
antifungal,[3] anti-inflammatory,[4] antimicrobial,[5] antidia-
betic,[6] inhibiting neuraminidase of influenza H1N1 virus,[7]
synthetic strategy for the preparation of these heterocyclic
compounds is the cyclization of thiourea derivatives with acet-
ylenedicarboxylates,[10,11] β-nitroacrylates,[12] α-haloketone,[13]
3-aryl-2-chloropropanals,[14] and α-halocarboxylic acids.[15,16]
Other methods include reaction of suitable amine with
benzaldehyde in the presence of an excess of mercaptoacetic
acid[17,18] and with chloroacetylchloride in the presence of am-
monium thiocyanate.[19] Venkata et al[20] reported multicom-
ponent synthesis using phenacyl bromide, thiosemicarbazide,
ethylacetoacetate, and aryl aldehydes for synthesis of thiazole
derivatives.
Anthraquinone and its derivatives are an important class
of heterocycles. They are found in plants such as aloe latex,
senna and rhubarb, fungi, and lichens and also in some in-
sects. These compounds attract dye molecules because of their
important role in various photochemical and colorimetric
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Heteroatom Chemistry. 2018;e21409.
https://doi.org/10.1002/hc.21409
wileyonlinelibrary.com/journal/hc
© 2018 Wiley Periodicals, Inc.
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O
O
OH
OH
O
O
O
O
OH
O
OH
OH
O
OH
O
HO
OH
COOH
H
O
O
topopyrone C
doxorubicin
rhein
NH2
FIGURE 1 Anthraquinone derivatives
O
O
S
O
S
+
C
Et3N,CH3CN
Reflux, 4h
N
N
R NH2
(2)
+
N
Br
R
X
X
(1)
(3)
X= H (4)
X= CH3(5)
O
R =
O
Cl
(b)
(c)
O
(a)
O
S
O
S
S
N
N
N
N
N
N
O
O
Cl
O
Cl
4b
5b
4a
O
O
S
S
N
N
N
N
SCHEME 1 Illustrative synthesis
of novel (4-phenylthiazol-2(3H)-ylidene)
benzamide derivatives
5c
4c
sensor systems. On the other hand, anthraquinones reveal a
wide range of application in synthetic and medicinal chem-
istry.[21,22] Anthraquinones are essential structural motifs in a
great number natural products such as emodin, aloe-emodin,
and rhein with cytotoxic properties; also, there are several
anthraquinone-based drugs such as mitoxantrone, ametan-
trone, and doxorubicin (Figure 1) used for treatment of vari-
ous cancer in clinic.[23]
directed toward combination of a five- or six-membered
heterocyclic ring such as thiazole in the anthracenedione
moiety.[25,26]
In view of the various activities of thiazole and anthra-
quinones, we have developed a research program focused on
the synthesis of new series of thiazole derivative and novel
anthraquinones-thiazole hybrids.
More recently, new series of heterocycles and
carbocycles-thiazole hybrids as important core structures
in many biologically active natural products and pharma-
ceuticals have been designed. In this regard, a series of
coumarin derivatives containing 2-methylbenzothiazoline
motif and related compounds were synthesized and evalu-
ated their radical scavenging activities.[24] Also, new com-
binations of quinazolinone derivatives by incorporating the
thiazole are synthesized. In most of these compounds, an-
algesic activity, anti-antibacterial, and anti-inflammatory
properties have been evaluated and proven. The problem of
multidrug resistance toward several anticancer compounds
has also become important, and much effort has been
2
RESULTS AND DISCUSSION
Synthesis of novel (4-phenylthiazol-
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2.1
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2(3H)-ylidene) benzamide
One-pot,multicomponentsynthesisofnovel(4-phenylthiazol-
2(3H)-ylidene) benzamide derivatives have been performed
using benzoylisothiocyanate derivatives (1), various amine
(2), and phenacyl bromide (3) in the presence of triethyl-
amine as a catalyst and hydrobromic acid scavenger in reflux
conditions (Scheme 1).
We started our investigation on the reaction in room
temperature conditions for 8 hours, but no suitable progress

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FIGURE 2 ORTEP view of molecular
structure of compound 4a. Ellipsoids are
drawn at their 30% probability level
FIGURE 3 ORTEP view of molecular
structure of molecules A (top) and B
(bottom) of compound 5b. Ellipsoids are
drawn at their 30% probability level
of the reaction was observed. To improve the reaction effi-
ciency, the reaction was carried out under reflux conditions.
The reaction products were isolated and were identified by
is discussed later in the text. Various amines, including sub-
stituted 2-furanmethylamine (a), 5-chloro-2-phenoxyaniline
(b), and 1-naphthylamine (c), were used to give new thiazole
derivatives.
For instance, in the FTIR spectrum of (Z)-N-(3-(furan-2-
ylmethyl)-4-phenylthiazol-2(3H)-ylidene) benzamide (4a),
C–H aliphatic and aromatic absorptions were observed at
1
FTIR, HNMR, 13CNMR spectra, mass spectrometry, and
CHNS elemental analysis. For compounds 4a and 5b, single
crystals of good quality adapted for X-ray diffraction analysis
were obtained, and the crystal structure of those compounds

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3056, 3025, and 2965 cm−1, respectively. Also absorption
at 1620 cm−1 corresponds to carbonyl group, and C=C
bond in thiazole ring exhibits absorption at 1566 cm−1. The
1H NMR spectrum showed the presence of 2 aliphatic pro-
tons at 5.45 ppm (CH2 − Cfurfurylamine ring), CH of thiazole at
6.57 ppm, and aromatic protons of phenyl and furfurylamine
rings at 8.40-6.24 ppm. The 13C NMR spectrum of this com-
pound showed carbonyl groups and carbon in thiazole ring at
174.22 and 168.80 ppm, respectively.
TABLE 1 Selected bond distances (Å) and angles (°) of
molecular structure of compound 4a
Bond lengths
(Å)
Bond
Bond
Bond
lengths (Å)
C1–C2
C1–S
C2–N2
C2–C16
C3–N1
C3–N2
1.335 (3)
1.730 (2)
1.401 (2)
1.481 (3)
1.305 (2)
1.361 (2)
C3–S
1.7464 (19)
1.230 (2)
1.372 (2)
1.496 (3)
1.476 (2)
C4–O1
C4–N1
C4–C5
C1–N2
Bond
Bond
Bond angles (°)
Bond
angles (°)
C2–C1–S
113.37 (15)
111.41 (17)
126.14 (17)
122.44 (15)
121.06 (16)
129.30 (14)
109.57 (13)
124.81 (19)
O1–C4–C5
N1–C4–C5
C3–N1–C4
C3–N2–C2
C3–N2–C11
C2–N2–C11
C3–S–C1
120.88 (17)
114.28 (16)
117.01 (16)
115.18 (14)
119.54 (15)
125.20 (14)
90.44 (10)
C1–C2–N2
C1–C2–C16
N2–C2–C16
N1–C3–N2
N1–C3–S
FIGURE 4 Partial crystal packing view of compound 5b
evidencing the distance in Å for pi-pi stacking of two adjacent A
molecules
N2–C3–S
O1–C4–N1
TABLE 2 Selected bond distances (Å) and angles (°) of molecular structure of compound 5b
Bond
Bond lengths (Å)a
Bond
Bond lengths (Å)a
C1–N1
C1–N2
C1–S1
C2–C3
C2–N2
C2–C24
1.308 (3) [1.311(3)]
1.373 (3) [1.369(3)]
1.741 (3) [1.741(3)]
1.333 (4) [1.333(3)]
1.407 (4) [1.414(3)]
1.470 (4) [1.466(4)]
C3–S1
C4–O1
C4–N1
C4–C5
C12–N2
1.720 (3) [1.718(3)]
1.240 (3) [1.238(3)]
1.367 (3) [1.373(3)]
1.485 (4) [1.481(4)]
1.436 (3) [1.443(3)]
Bond
Bond angles (°)a
Bond
Bond angles (°)a
N1–C1–N2
N1–C1–S1
N2–C1–S1
C3–C2–N2
C3–C2–C24
N2–C2–C24
C2–C3–S1
O1–C4–N1
120.9 (3) [121.8(2)]
129.6 (2) [128.3(2)]
109.5 (2) [109.85(19)]
111.2 (3) [111.0(2)]
126.0 (3) [125.5(2)]
122.3 (3) [123.3(2)]
113.9 (3) [114.1(2)]
124.0 (3) [124.1(3)]
O1–C4–C5
N1–C4–C5
C1–N1–C4
C1–N2–C2
C1–N2–C12
C2–N2–C12
C3–S1–C1
120.8 (3) [119.7(3)]
115.2 (3) [116.1(2)]
115.7 (3) [115.7(2)]
114.6 (2) [114.4(2)]
120.6 (3) [121.9(2)]
123.4 (2) [123.5(2)]
90.68 (16) [90.58(13)]
aData in parenthesis refer to molecule B in Figure 2.

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The mass spectrometry and CHNS elemental analysis
present, and in Table 2, the geometrical parameters of mole-
cule B are reported in the parenthesis.
confirmed the proposed structure. The molecular structure
of compounds 4a and 5b was established unequivocally by
single-crystal X-ray diffraction analysis. The ORTEP views
of molecular structure of compounds 4a and 5b are reported
in Figures 2 and 3, respectively, together with the atomic
numbering scheme.
The most important difference between the two molecules
A and B of compound 5b regards the dihedral angle between
the mean plane of the system defined by atoms C1, C2, C3,
C4, O1, N1, N2 and S and that of the p-tolyl substituent. In
fact, in molecule A, the dihedral angle is of 3.85° while in
molecule B is of 26.47°. Considering the crystal packing, the
better overall planarity of molecule A in compound 5b allows
a stacking of molecules at a distance of 3.368 Å as evidenced
in Figure 4.
Tables 1 and 2 show a list of the most important bond and
angles. In the crystals of compound 5b, two crystallographic
independent but similar molecules (molecule A and B) are
In the molecular structure of compounds 4a and 5b, the
moiety defined by atoms C1, C2, C3, C4, O1, N1, N2 and
S is almost planar with maximum deviation for atom O1 of
0.064 Å for 4a and 0.021 Å [0.016 Å for molecule B] for 5b.
Moreover, the substituted phenyl ring forms a dihedral angle
of 24.72° and 39.52° [42.52° for molecule B] in compounds
4a and 5b, respectively.
S
O
O
R
O
S
CH3CN
N
H
C
N
N
O
R NH2
H
Br
X
3
Et3N
X
2
1
O
O
S
A proposed mechanism for the reaction is given in
Scheme 2. (4-Phenylthiazol-2(3H)-ylidene) benzamide de-
rivatives are synthesized via one-pot, two-step cyclocon-
densation. In the first step, benzoylisothiocyanate (1) reacts
with heterocyclic aliphatic or aromatic amines (2) to pro-
duce N-(carbamothioyl) benzamide as an unsymmetrical
S
-H2O
N
NH
N
R
N
R
X
X
SCHEME 2 Proposed mechanism for the synthesis of
(4-phenylthiazol-2(3H)-ylidene) benzamide derivatives
S
O
O
O
NH2
O
NH
N
H
CH3CN
Reflux
N
R1
C
S
R1
R1
O
(6)
O
(8a-e)
(7)
O
S
O
S
N
O
O
R2
CH3COOH
Reflux
O
O
N
O
O
O
NH
N
O
H
C
C
C
C
R2O
OR2
R1
O
(9)
R1 = H (10),Cl (11), CH3(12)
R
2 = CH3 (a) , CH2CH3 (b)
CH3
Cl
O
O
O
S
O
O
CH3
S
S
O
O
O
O
CH3
N
O
CH3
O
N
N
O
N
O
O
O
N
N
Cl
O
O
O
(12a)
(11a)
(10a)
O
O
S
O
O
CH2CH3
S
O
O
CH2CH3
N
N
O
O
O
N
O
N
SCHEME 3 Illustrative synthesis
of novel (benzoylimino)-3-((9,10-dioxo-9,
10-dihydroanthracen-1-yl)-4-oxothiazolidin-
5-ylidene) acetate derivative
O
O
(11b)
(10b)

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thiourea. In the next step, the condensation and cyclization
reaction is carried out through a nucleophilic attack on
phenacyl bromide (3). Finally, the water is removed to pro-
duce the final product.
2.2
Synthesis of novel (benzoylimino)-3-
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((9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-
oxothiazolidin-5-ylidene)acetate
Synthesis of novel hybrid structures that include both anth-
raquinone and thiazole ring has been described in the literature.
The reaction have been performed using N,N′-disubstituted
asymmetric thioureas with dialkyl acetylenedicarboxylate
(Scheme 3).
For our initial investigation, N-(9,10-dioxo-4a,9,9a,10-
tetrahydroanthracen-1-ylcarbamothioyl) benzamide with
DMAD was taken as the model reaction. We began this study
by performing the reaction in ethanol, acetonitrile, dimethyl-
formamide, and acetic acid at room temperature as well as at
reflux temperature. The best reaction conditions were opti-
mized in acetic acid at reflux temperature. Illustrative mecha-
nism for the generation of compounds is shown in Scheme 4.
In the first step, aminoanthraquinone (6) reacts with ben-
zoylisothiocyanate (7) to produce N-(9,10-dioxo-4a,9,9a,10-
tetrahydroanthracen-1-ylcarbamothioyl)-4-methylbenzamide
derivative (8) as an unsymmetrical thiourea. In the next step,
cyclocondensation reaction and cyclization via by DMAD (9)
FIGURE 5 ORTEP view of compound 11a, evidencing the
formation of dimers between molecules of acetic acid. Ellipsoids are
depicted at their 30% probability level. Symmetry code = −x, −y, −z
and unsymmetrical thiourea. Finally, the alcohol is removed
to produce the final product.
The FTIR spectrum of these compounds was observed
C–H aliphatic and aromatic absorptions. Also absorption at
1737-1733 cm−1 corresponds to carbonyl ester group. The 1H
NMR spectra of product in Scheme 2 contained vinyl proton
S
O
O
O
HN
N
H
O
O
NH2
O
CH3CN
Reflux
R1
N
C
S
R1
(7)
(6)
(8)
O
O
O
R1
C
C
C
C
C
O
R2O
OR2
(9)
R2O
O
C
C
H
C
OR2
S
O
S
O
S
O
O
R2
CH3COOH
Reflux
N
O
CH3COOH
Reflux
O
O
HN
N
N
O
N
O
O
HN
H
R1
R
O
R1= H, Cl, CH3
R2= CH3,CH2CH3
SCHEME 4 Proposed mechanism for the synthesis of ((benzoylimino)-3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxothiazolidin-5-
ylidene) acetate

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The formation of a thiazole ring was also clearly confirmed
by the 13C NMR spectra. The mass spectrometry and CHNS
elemental analysis confirmed the proposed structure.
The exact nature of compounds 11a and 11b was es-
tablished unequivocally by single-crystal X-ray diffraction
analysis. The molecular structure of the complexes is very
similar but in the crystals of 11a, acetic acid molecules
are also present. The molecules of acetic acid are involved
in a strong hydrogen bond forming dimers. [O7···O8′
2.673(2) Å, H7···O8′ 1.884(3) Å, O7-H7···O8′161.24(3)°].
The ORTEP view of compound 11a and 11b is reported in
Figures 5 and 6 respectively, together with the atomic num-
bering scheme; a list of the most important bond distances
and angles is reported in Tables 3 and 4, respectively, for
compound 11a and 11b. The two molecules are very similar,
and the only difference is the presence of an ethyl moiety
in 11b instead of a methyl group in 11a in the esoteric part
of the compound. Analyzing the bond distances and angles
in both compounds, they are very similar and in agreement
with those observed in the literature for relating fragments
in compounds reported. If we exclude the anthraquinone
ring connected to the N1 atom, the molecule is planar in
11a and also in 11b. The dihedral angle between the mean
plane of the molecule, excepted the anthraquinone moiety,
FIGURE 6 ORTEP view of compound 11b. Ellipsoids are
depicted at their 30% probability level
singlet at 7.15 ppm and aromatic protons of phenyl and anthra-
quinone rings at 8.67-7.27 ppm also showed the presence of
methoxy in compounds (10a-12a) at 3.97 ppm and moreover
methyl proton singlet at 3.96 ppm for 12a. Aliphatic protons
for 10b and 11b (CH2CH3) are seen at 1.44 and 2.13 ppm.
TABLE 3 Selected bond distances (Å) and angles (°) of molecular structure of compound 11a
Bond
Bond lengths (Å)
Bond
Bond lengths (Å)
C1–N1
1.445 (3)
1.386 (3)
1.488 (4)
1.333 (4)
1.750 (3)
1.282 (3)
1.382 (3)
1.756 (3)
C18–O4
C18–N2
C18–C19
C25–C26
C26–O5
C26–O6
C27–O6
1.222 (3)
1.397 (3)
1.486 (4)
1.463 (4)
1.205 (3)
1.337 (3)
1.453 (3). ?
C15–N1
C15–C16
C16–C25
C16–S1
C17–N2
C17–N1
C17–S1
Bond
Bond angles (°)
Bond
Bond angles (°)
C2–C1–C6
C2–C1–N1
C6–C1–N1
121.02 (16)
117.99 (16)
120.96 (15)
124.59 (17)
126.82 (18)
108.59 (15)
121.54 (18)
126.62 (15)
111.83 (14)
119.20 (15)
128.97 (13)
111.82 (13)
123.59 (19)
O4–C18–C19
N2–C18–C19
C16–C25–C26
O5–C26–O6
O5–C26–C25
O6–C26–C25
C28–C27–O6
C17–N1–C15
C17–N1–C1
C15–N1–C1
C17–N2–C18
C26–O6–C27
C16–S1–C17
122.21 (16)
114.18 (15)
120.27 (19)
124.5 (2)
124.0 (2)
111.49 (19)
107.3 (2)
116.97 (14)
120.72 (15)
121.94 (14)
118.17 (15)
115.68 (19)
90.67 (9)
O3–C15–N1
O3–C15–C16
N1–C15–C16
C25–C16–C15
C25–C16–S1
C15–C16–S1
N2–C17–N1
N2–C17–S1
N1–C17–S1
O4–C18–N2

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TABLE 4 Selected bond distances (Å) and angles (°) of molecular structure of compound 11b
Bond
Bond lengths (Å)
Bond
Bond lengths (Å)
C1–N1
1.439 (2)
1.204 (2)
1.388 (2)
1.496 (2)
1.335 (3)
1.750 (2)
1.285 (2)
1.377 (2)
1.7612 (18)
C18–O4
C18–N2
C18–C19
C25–C26
C26–O5
C26–O6
C27–C28
C27–O6
1.222 (2)
1.399 (2)
1.474 (3)
1.480 (3)
1.199 (3)
1.325 (3)
1.459 (4)
1.462 (3)
C15–O3
C15–N1
C15–C16
C16–C25
C16–S1
C17–N2
C17–N1
C17-S1?
Bond
Bond angles (°)
Bond
Bond angles (°)
C2–C1–C6
C2–C1–N1
C6–C1–N1
121.02 (16)
117.99 (16)
120.96 (15)
124.59 (17)
126.82 (18)
108.59 (15)
121.54 (18)
126.62 (15)
111.83 (14)
119.20 (15)
128.97 (13)
111.82 (13)
123.59 (19)
O4–C18–C19
N2–C18–C19
C16–C25–C26
O5–C26–O6
O5–C26–C25
O6–C26–C25
C28–C27–O6
C17–N1–C15
C17–N1–C1
C15–N1–C1
C17–N2–C18
C26–O6–C27
C16–S1–C17
122.21 (16)
114.18 (15)
120.27 (19)
124.5 (2)
124.0 (2)
111.49 (19)
107.3 (2)
116.97 (14)
120.72 (15)
121.94 (14)
118.17 (15)
115.68 (19)
90.67 (9)
O3–C15–N1
O3–C15–C16
N1–C15–C16
C25–C16–C15
C25–C16–S1
C15–C16–S1
N2–C17–N1
N2–C17–S1
N1–C17–S1
O4–C18–N2
1
and the mean plane of the anthraquinone ring is 80.66(2)°
and 86.47(3)° for 11a and 11b, respectively.
9100 apparatus. HNMR and 13CNMR spectra of com-
pounds were recorded on a Bruker DRX-400 Avance in-
strument in CDCl3. The mass spectra were recorded on
an Agilent Technology HP 5973 MSD mass spectrometer
operating at an ionization potential of 70 eV. Elemental
analyses were performed using a Heraeus CHNS Rapid
analyzer.
The presence of the acetic acid in the crystals of 11a
affects the crystal packing of the compounds. In fact, the
molecule, been formed by extended planar systems, can
produce π··· π stacking in the crystal packing. This is ev-
ident in the case of 11b, in which interplanar distance of
3.318(2) Å is present between the anthraquinone rings as
shown in Figure 7 (ii). The planar system of the rest of the
molecule is stacked in the crystal packing at a distance of
3.362(2) Å, Figure 7 (i). In the case of the crystal packing
of compound 11a, the presence of the dimers of acetic acid
in the unit cell prevents the stacking of the molecules as
shown in Figure 7 (iii).
3.2
General procedure for synthesis of
|
novel (4-phenylthiazol-2(3H)-ylidene)
benzamide
At first, the benzoyl isothiocyanate derivative was pre-
pared by adding benzoyl chloride derivative (1 mmol) to
ammonium thiocyanate (1 mmol) in 5 mL of acetonitrile
and refluxed for 20 minutes. The reaction mixture was fil-
tered, and the solution was added to the appropriate amine
(1.0 mmol) and phenacyl bromide (1.1 mmol) in acetoni-
trile (5 mL) and stirred at reflux conditions in the presence
of triethylamine (1.0 mmol, 0.10 g) for a period of time
(specified hour or minutes). The progress of the reaction
was monitored by thin-layer chromatography (TLC). After
completion of the reaction, the mixture was filtered. The
3
EXPERIMENTAL
General
|
3.1
|
The reagents and solvents were purchased from Merck and
Aldrich Chemical companies. The products were analyzed
by FTIR spectroscopy (JASCO FT/IR-460 plus spectrom-
eter), and melting points were measured by Electrothermal

HOSSAINI et Al.
9 of 12
|
FIGURE 7 Crystal packing of
compound 11b (top) and 11a (bottom),
evidencing the π···π stacking of molecules
in the case of compound 11b (i) and (ii).
In 11a (iii), the presence of acetic acid
molecules prevents the stacking of the
molecules. The interplanar distances are
given in Å
residue was washed with acetonitrile and recrystallized
from ethanol for further purification. The isolated com-
in room temperature and then gently refluxed. (The reaction
was monitored by TLC analyses.) After completion of the re-
action, the products obtained were collected by filtration, and
the residue was washed and recrystallized from acetonitrile
for further purification. The isolated compounds were con-
firmed by FTIR, 1HNMR, 13CNMR, and mass spectroscopy.
1
pounds were confirmed by FTIR, HNMR, 13CNMR, and
mass spectroscopy.
3.3
General procedure for synthesis of
|
N,N′-disubstituted asymmetric thioureas (8a-e)
3.4.1
Spectral data
|
Benzoyl isothiocyanate derivative was prepared by adding
benzoyl chloride derivative (1 mmol) to ammonium thio-
cyanate (1 mmol) in 5 mL of acetonitrile and refluxed for
20 minutes. The reaction mixture was filtered, and the so-
lution was added to the 1-aminoanthraquinone (1.0 mmol,
0.223 g) and 20 mL of acetonitrile in the reflux conditions.
The progress of reaction was followed by TLC. The products
obtained were collected by filtration and washed with ace-
tonitrile several times.
(Z)-N-(3-(furan-2-ylmethyl)-4-phenylthiazol-2 (3H)-ylidene)
benzamide (4a): light yellow crystals, m.p. = 149-150°C IR
(KBr) ν/cm−1 3056, 3025 (C–H aromatic), 2965 (CH aro-
matic), 1620 (C=O), 1601 &1472 (C=C, aromatic), 1566
1
(C=C thiazole), 1493; HNMR (400 MHz, CDCl3) δ 8.40
(2H, d, J 6.8 Hz CH), 7.44-7.57 (5H, m CH), 7.44-7.42 (3H,
m CH), 7.30 (1H, d, J 7.6 Hz CH), 6.57 (1H, s CH thiazole),
6.28 (1H, d CH furan), 6.24 (1H, d CH furan), 5.45 (2H, s
CH2); 13C NMR (100 MHz, CDCl3) δ 174.22, 168.80, 149.01,
142.17, 139.11, 136.93, 131.56, 130.43, 129.83, 129.78,
129.37, 128.83, 128.11, 110.64, 109.32, 107.24, 43.61; MS
(EI, 70 eV) m/z (%): 360 (M+), 255 (105), 279 (81), Anal.
Calcd. for C21H16N2O2S: C: 70.00, H: 4.44, N: 7.77, S: 8.90;
found: C: 70.09, H: 4.41, N: 7.69, S: 8.92.
(Z)-N-(3-(5-chloro-2-phenoxyphenyl)-4-phenylthiazol-
2(3H)-ylidene) benzamide (4b): white crystals, m.p. = 199-
200°C. IR (KBr) ν/cm−1 3051 (C–H aromatic), 1688 (C=O),
1600 & 1455 (C=C, aromatic), 1567 (C=C thiazole), 1491;
1HNMR (400 MHz, CDCl3) δ 8.17 (2H, d, CH benzene), 7.62
3.4
General procedure for synthesis of
|
novel (benzoylimino)-3-(9,10-dioxo-9,10-
dihydroanthracen-1-yl)-4-oxothiazolidin-5-
ylidene)acetate
Into a 100-cm3 two-necked round bottom flask containing a
solution of 8a-e (1 mmol) in glacial acetic acid (50-80 mL),
(1 mmol) dimethyl acetylenedicarboxylate (DMAD) or die-
thyl acetylenedicarboxylate (DEAD) was added in a dropwise
fashion with stirring. The mixture was stirred for 30 minutes

10 of 12
HOSSAINI et Al.
|
TABLE 5 Details for the X-ray data collection for compounds 4a, 5c, 11a, and 11b
Compound
4a
5c
11a
11b
Formula
Molecular weight
Crystal system
Space group
C21H16N2O2S
360.42
Monoclinic
P21/n
C29H21ClN2O2S
496.99
Triclinic
P − 1
C29H19ClN2O8S
590.97
Triclinic
P − 1
C28H17ClN2O6S
544.94
Triclinic
P − 1
a/Å
b/Å
c/Å
α/°
β/°
γ/°
13.064 (8)
9.962 (6)
14.058 (9)
90
102.540 (10)
90
1785.9 (19)
4
1.340
12.506 (2)
14.034 (4)
15.414 (5)
77.961 (3)
72.726 (2)
77.687 (3)
2493.1 (11)
4
8.1996 (12)
11.5559 (16)
15.985 (2)
69.586 (2)
78.862 (3)
71.784 (2)
1342.3 (3)
2
10.187 (3)
11.411 (4)
12.051 (4)
113.341 (5)
98.690 (5)
99.822 (5)
1229.8 (7)
2
Volume (Å3)
Z
Dcalc/g cm−3
1.324
1.462
1.472
F(000)
752
0.199
24 397
4427
1032
0.266
27 583
8786
608.0
0.276
11 672
3518
560.0
0.289
20 584
7665
μ(Mo-Kα)/mm−1
Reflections collected
Unique reflections
Observed reflections
[I > 2σ(I)]
3151
[Rint = 0.0273]
4822
[Rint = 0.0630]
2691
[Rint = 0.0299]
4943
[Rint = 0.0357]
R, wR [I > 2σ((I)]
R = 0.0481
wR = 0.1340
R = 0.0478
wR = 0.0989
R = 0.0408
wR = 0.0981
R = 0.0501
wR = 0.1669
R, wR [all data]
R = 0.0694
wR = 0.1507
R = 0.1052
wR = 0.1218
R = 0.0579
wR = 0.1084
R = 0.0814
wR = 0.2032
R = Σ|Fo − Fc|/Σ|Fo|; wR = [Σ[w(Fo2 − Fc2)2]/Σ[w(Fo2)2]]1/2
.
(1H, d, CH) 7.50 (1H, d, CH), 7.48-7.37 (3H, m, CH), 7.35-
7.28 (5H, m, CH), 7.16 (2H, d, CH) 7.07 (1H, t, CH), 6.74 (1H,
d CH), 6.69 (1H, s, CH thiazole), 6.60 (2H, d, CH)); 13CNMR
(100 MHz, CDCl3) δ 174.49, 170.06, 154.95, 151.78, 139.02,
136.61, 131.64, 130.85, 130.47, 130.41, 129.71, 129.40,
129.12, 128.17, 128.61, 128.55, 128.06, 127.38, 124.53,
119.49, 118.96, 107.00; MS (EI, 70 eV) m/z (%): 482 (M+),
484 (M + 2), 405 (77), 203, 105; MS (EI, 70 eV) m/z (%):
Anal. Calcd. for C28H19ClN2O2S: C: 69.70, H: 3.94, N: 5.80,
S: 6.65; found: C: 69.73, H: 3.91, N: 5.78, S: 6.63.
(Z)-N-(3-(5-chloro-2-phenoxyphenyl)-4-phenylthiazol-
2(3H)-ylidene)-4-methylbenzamide (5b): light green crystals,
m.p. = 176-177°C. IR (KBr) ν/cm−1 3058, 3033 (C–H aro-
matic), 1600 &1454 (C=C, aromatic) 1562 (C=C thiazole),
1461; 1HNMR (400 MHz, CDCl3) δ 8.084 (2H, d, J 8.00 Hz
CH benzene), 7.62 (1H d), 7.38 (1H, d), 7.37-7.38 (5H, m),
7.24 (2H, d, CH), 7.27 (2H, t, J 8.00 Hz CH benzene), 7.05
(1H, t CH), 6.73 (1H, d CH), 6.67 (1H, s CH thiazole), 6.60
(2H, d CH) 2.42 (3H, s CH3); 13C NMR (100 MHz, CDCl3)
δ 174.50, 169.86, 154.97, 151.75, 142.07, 138.93, 133.98,
130.92, 130.47, 130.42, 129.71, 129.47, 129.08, 128.43,
128.58, 128.54, 128.05, 127.37, 124.51, 119.47, 118.97,
106.93, 21.96 ppm. MS (EI, 70 eV) m/z (%):496 (M+), 498
(M + 2), 377 (119), 77; MS (EI, 70 eV) m/z (%): Anal. Calcd.
for C29H21ClN2OS, C: 70.16, H: 4.23, N: 5.64, S: 6.46; C:
70.18, H: 4.20, N: 5.61, S: 6.43.
(Z)-N-(3-(naphthalen-1-yl)-4-phenylthiazol-2(3H)-
ylidene) benzamide (4c): white powder, m.p. = 209-210°C,
IR (KBr) ν/cm−1 3051 (C–H aromatic), 1683 (C=O), 1592 &
1464 (C=C, aromatic), 1562 (C=C thiazole), 1510 (C=N);
1HNMR (400 MHz, CDCl3) δ 7.96 (2H, d, J 8.0 Hz CH
benzene), 7.83 (2H, d, J 7.2 Hz CH naphthyl), 7.58 (1H, t
CH), 7.5-7.48 (2H, dd, CH), 7.36 (2H, t), 7.26-7.17 (4H, m),
7.11 (4H, d), 6.86 (1H, s, CH thiazole); 13CNMR (100 MHz,
CDCl3) δ 174.69, 169.97, 139.97, 136.60, 134.59, 134.04,
131.38, 130.41, 130.15, 129.68, 129.25, 128.94, 128.50,
128.41, 128.24, 127.80, 127.40, 126.93, 126.59, 125.11,
123.00, 107.24; MS (EI, 70 eV) m/z (%): 406 (M+), 329 (77),
301 (105), 127; Anal. Calcd. for: C26H18N2OS: C: 76.84, H:
4.43, N: 6.89, S: 7.89, found: C: 76.80, H: 4.45, N: 6.90,
S7.79.
(Z)-N-(3-(naphthalen-1-yl)-4-phenylthiazol-2(3H)-
ylidene) benzamide (5c): white powder, m.p. = 197-198°C,
IR (KBr) ν/cm−1 3051 (C–H aromatic), 2913 (C–H aliphatic),
1694 (C=O), 1594 & 1470 (C=C, aromatic), 1556 (C=C thi-
azole), 1511 (C=N); 1H NMR (400 MHz, CDCl3) δ 7.95 (2H,

HOSSAINI et Al.
11 of 12
|
d, J 8.0 Hz CH benzene), 7.72 (2H, d, CH naphthyl), 7.60-
7.46 (4H, m), 7.36 (2H, d), 7.18 (1H, dd), 7.11(4H, d), 7.03
(2H, d, J 8.0 Hz CH benzene), 6.84 (1H, s CH thiazole), 2.29
(3H, s CH3); 13CNMR (100 MHz, CDCl3) δ 174.69, 169.75,
141.78, 139.89, 134.64, 134.04, 133.96, 130.46, 130.18,
129.64, 129.32, 128.91, 128.57, 128.49, 128.39, 128.23,
127.36, 129.97, 126.56, 125.12, 123.06, 107.19, 21.56; MS
(EI, 70 eV) m/z (%): MS (EI, 70 eV) m/z (%): 420 (M+), 301
(119), 105, 91; Anal. Calcd. for: C27H20N2OS, C: 77.14, H:
4.76, N: 6.66, S: 7.63, found: C: 77.17, H: 4.73, N: 6.67, S:
7.61.
511 (M + 1), 451 (59), 391 (119), 275, 91. Anal. Calcd. For:
C30H18N2O6S, C: 67.43, H: 3.37, N: 5.24, S: 6.00, found: C:
67.46, H: 3.35, N: 5.23, S: 6.01.
(E)-Ethyl
2-((Z)-2-(benzoylimino)-3-(9,10-dioxo-9,10-
dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)acetate
(10b): Brown crystal, m.p. = 272°C, IR (KBr) ν/cm−1: 3027,
1
2979, 1734, 1717, 1691, 1672, 1654. HNMR (400 MHz,
CDCl3) δ; 8.67 (1H, d J = 8), 8.34 (1H, d J = 5.6), 8.16
(1H, d, J = 5.6), 8.059 (1H, t J = 8), 7.87-7.75 (5H, m), 7.28
(2H, d), 7.15 (1H, s), 4.42 (2H, q), 1.44 (3H, t). 13CNMR
(100 MHz, CDCl3) δ; 182.11, 182.02, 175.79, 167.61,
165.14, 165.09, 140.64, 136.30, 135.52, 134.62, 134.50,
134.43, 133.75, 133.54, 133.04, 132.58, 131.48, 131.39,
129.77, 128.65, 128.57, 127.66, 127.62, 127.16, 121.64,
62.22, 14.26. MS (EI, 70 eV) m/z (%): 510 (M+) 405 (105),
275, 77. Anal. Calcd. For: C28H18N2O6S, C: 65.90, H: 3.52,
N: 5.48, S: 6.28, found: C: 65.92, H: 3.51, N: 5.46, S: 6.07.
(E)-Ethyl 2-((Z)-2-(4-chlorobenzoylimino)-3-(9,10-dioxo-
9,10-dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)
acetate (11b): Mustard crystal, m.p. = 273°C, IR (KBr) ν/
cm−1: 3064, 2982, 1733, 1692, 1671, 1643, 1613, 1579.
H1NMR (400 MHz, CDCl3) δ; 8.66 (1H, d J = 8), 8.33 (1H,
d J = 7.2), 8.15 (1H, d J = 7.2), 8.05 (1H, t J = 8), 7.88 (2H,
d), 7.87-7.76 (3H, m), 7.31 (2H, d), 7.29 (1H, d), 7.14 (1H,
s), 4.41 (2H, q), 1.43 (3H, t). C13NMR (100 MHz, CDCl3)
δ; 182.19, 182.01, 176.73, 166.82, 165.21, 165.10, 140.85,
136.39, 135.50, 134.59, 134.51, 134.43, 134.35, 133.80,
133.64, 133.44, 132.59, 130.13, 130.05, 129.70, 128.62,
128.30, 127.68, 127.63, 127.11, 126.47, 121.36, 62.05, 14.27.
MS (EI, 70 eV) m/z (%): 544 (M+), 545 (M + 1), 510, 471,
391 (139), 275, 105, 77. Anal. Calcd. For: C28H17ClN2O6S,
C: 61.61, H: 3.29, N: 5.13, S: 5.78, found: C: 61.60, H: 3.28,
N: 5.16, S: 5.77.
(E)-Methyl 2-((Z)-2-(benzoylimino)-3-(9,10-dioxo-9,10-
dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)acetate
(10a): Slime green powder, m.p. = 277°C, IR (KBr) ν/cm−1:
1
3065, 2946, 1735, 1697, 1671, 1642, 1613, 1580. HNMR
(400 MHz, CDCl3) δ: 8.66 (1H, d J = 8), 8.34 (1H, d J = 5.6),
8.16 (1H, d, J = 5.6), 8.061 (1H, t J = 8), 7.88 (2H, d), 7.82
(2H, m), 7.47 (1H, t), 7.31 (3H, m), 7.15 (1H, s), 3.97 (3H, s).
13C NMR (100 MHz, CDCl3) δ; 182.18, 182, 176.75, 166.70,
165.53, 165.16, 141.15, 136.38, 135.51, 134.60, 134.47,
134.44, 133.79, 133.62, 133.47, 132.59, 130.14, 130.06,
129.72, 128.60, 128.31, 127.71, 127.64, 127.12, 120.84,
52.81. MS (EI, 70 eV) m/z (%): 496 (M+), 391 (105), 275,
105, 77. Anal. Calcd. For: C27H16N2O6S, C: 65.34, H: 3.22,
N: 5.64, S: 6.46, found: C: 65.36, H: 3.24, O: 19.30, N: 5.61,
S: 6.48.
(E)-Methyl 2-((Z)-2-(4-chlorobenzoylimino)-3-(9,10-dio-
xo-9,10-dihydroanthracen-1-yl)-4-oxothiazolidin-5-ylidene)
acetate (11a): Slime green powder, m.p. = 275°C, IR (KBr)
ν/cm−1: 3061, 2927, 1735, 1709, 1673, 1646, 1624, 1587,
1HNMR (400 MHz, CDCl3) δ; 8.66 (1H, d J = 8), 8.33 (1H,
d J = 7.2), 8.16 (1H, d J = 7.2), 8.06 (1H, t J = 8), 7.87-7.77
(4H, m), 7.29 (1H, d), 7.25 (2H, d), 7.15 (1H, s), 3.97 (3H,
s). 13CNMR (100 MHz, CDCl3) δ; 182.10, 82.01, 177.15,
167.48, 165.52, 165.06, 140.95, 139.93, 136.29, 135.52,
134.62, 134.50, 133.74, 133.51, 133, 132.58, 131.48, 131.40,
129.78, 128.65, 128.56, 127.61, 127.16, 121.10, 52.84. MS
(EI, 70 eV) m/z (%): 530 (M+), 511 (M + 1), 471 (59), 391
(139), 275, 111. Anal. Calcd. For: C27H16ClN2 O6S, C: 61.10,
H: 2.82, N: 5.27, S: 6.02, found: C: 61.11, H: 2.80, N: 5.23,
S: 6.03.
3.5
Experimental details of X-ray
|
diffraction analysis for compounds 4a, 5b,
11a, and 11b
The crystallographic data for the complexes were collected
at room temperature on a Bruker APEX II single-crystal dif-
fractometer, working with Mo-Kα graphite monochromatic
radiator (λ = 0.71073 Å) and equipped with an area detector.
The raw frame data (20 seconds per frame scan time for a
sphere of diffraction data) were processed using SAINT soft-
ware [SAINT, Version 7.06a; Bruker AXS Inc.: Madison,
Wisconsin, USA]; a correction for absorption was made
using SCALE program [G. M. Sheldrick, SADABS 2000
Version 2.01, Bruker AXS Inc., Madison, Wisconsin, USA]
to yield the reflection data file. The structures were solved by
direct methods with SHELXS-97 and refined against F2 with
SHELXL-2014/7[27] using anisotropic thermal parameters
for all nonhydrogen atoms. The hydrogen atoms were placed
in the ideal geometrical positions. Details for the X-ray data
(E)-Methyl 2-((Z)-3-(9,10-dioxo-9,10-dihydroanthracen-
1-yl)-2-(4-methylbenzoylimino)-4-oxothiazolidin-5-ylidene)
acetate (12a): Slime green crystal, m.p. = 271°C, IR (KBr)
ν/cm−1: 3067, 2956, 1737, 1690, 1679, 1649, 1605, 1588.
1HNMR (400 MHz, CDCl3) δ; 8.66 (1H, d J = 8), 8.33 (1H,
d J = 5.6), 8.16 (1H, d J = 5.6), 8.05 (1H, t J = 8), 7.86-
7.76 (5H, m), 7.14 (1H, s), 7.10 (2H, d), 3.96 (3H, s), 2.34
(3H, s). 13CNMR (100 MHz, CDCl3) δ; 128.20, 181.97,
176.63, 166.13, 165.54, 165.18, 144.43, 141.27, 136.41,
135.49, 134.57, 134.41, 133.80, 133.67, 132.58, 131.92,
130.25, 130.16, 129.67, 129.07, 128.61, 127.65, 127.10,
120.66, 52.79, 21.73. MS (EI, 70 eV) m/z (%): 510 (M+),

12 of 12
HOSSAINI et Al.
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collection are reported in Table 5. Crystallographic data
for the complexes have been deposited with the Cambridge
Crystallographic Data Centre as supplementary publications
CCDC.
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4
CONCLUSION
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In conclusion, we have introduced an efficient and fac-
ile approach for the synthesis of novel thiazole deriva-
tives. In the first approach, synthesis of some novel
(4-phenylthiazol-2(3H)-ylidene) benzamide derivatives via
one-pot and multicomponent reaction between benzoyli-
sothiocyanate, various amines, and phenacyl bromide was
performed under reflux conditions. The reaction is mainly
condensation followed by cyclization. Initially, unsymmetri-
cal thiourea was synthesized then cyclocondensation reac-
tion and cyclization via by attacked nucleophile to phenacyl
bromide. In the second method, new anthraquinone-thiazole
hybrids were synthesized from condensation of the unsym-
metrical thiourea with anthraquinone and DMAD or DEAD.
These new compounds were fully characterized, and the
single-crystal X-ray diffraction analysis reveals clearly the
exact identity of the compounds. The benefits of the pre-
sented method are one-pot, excellent yields, simple work-up,
and the lack of need for column chromatography.
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