Synthesis and crystal structure of new heterocyclic compounds containing 1,2,3-triazole moiety

Article abstract of DOI:10.1007/s10870-011-0063-1

A series of new heterocyclic compounds bearing 1,2,3-triazole moiety were synthesized using 4-acetyl-2-phenyl-1,2,3-triazole 1 as the starting material. The target compounds were prepared and the structures were characterized by IR, ¹H NMR, MS

Full text of DOI:10.1007/s10870-011-0063-1

J Chem Crystallogr (2011) 41:1158–1164
DOI 10.1007/s10870-011-0063-1
ORIGINAL PAPER
Synthesis and Crystal Structure of New Heterocyclic Compounds
Containing 1,2,3-Triazole Moiety
•
Zhi-Qiang Dong Fang-Ming Liu Yong-Ming Zeng
•
Received: 28 December 2010 / Accepted: 7 March 2011 / Published online: 30 March 2011
Ó Springer Science+Business Media, LLC 2011
Abstract A series of new heterocyclic compounds bear-
ing 1,2,3-triazole moiety were synthesized using 4-acetyl-
2-phenyl-1,2,3-triazole 1 as the starting material. The
target compounds were prepared and the structures were
characterized by IR, 1H NMR, MS and elemental analysis.
Meanwhile, the crystal structures of the synthesized com-
pounds were also furthered confirmed by X-ray diffraction
analysis. Compound 3b crystallized in the monoclinic
P2(1)/c space group with unit cell parameters a =
Introduction
In recent years, interests of researchers have been focused on
the nitrogen-, sulfur-, and oxygen-containing heterocyclic
compounds owing to their wide range of applications and
biological activities. Compounds possessing isoxazole or
oxadiazoline moiety are associated with diverse pharmaco-
logical activities [1–3]. Also, 1,2,4-triazolo[3,4-b][1,3,4]thi-
adiazine derivatives have been reported to exhibit analgesic,
antihelmintic, antitubercular, antiviral, antifungal, and anti-
cancer properties [4–9]. On the other hand, the synthesis of
1,2,3-triazole-containing compounds have been of growing
interest in the medicine industry. The 1,2,3-triazole scaffolds
are considered as significant synthetic targets due to their
significant biological activity as antibacterial [10], anti-HIV
[11], antimicrobial [12] agents, and b3-adrenergic receptor
agonist [13]. Recently, click chemistry has been emerged as a
excellent and efficient method for the synthesis of new
chemical entities and the generation of large number of drug-
like molecules with 1,2,3-triazole nucleus [14]. In the study of
pharmaceuticals, the introduction of a 1,2,3-triazole ring into
the parent compounds is expected to influence the biological
activities. Encouraged by all these facts and as a continuation
of our program directed towards the synthesis of new het-
erocyclic compounds bearing 1,2,3-triazole moiety [15, 16], it
was thought worthwhile to undertake the synthesis of the title
compounds with both active pharmacophores in a single
molecular framework, which may have potential biological
and medical applications.
˚
˚
˚
10.6974(17) A, b = 20.356(3) A, c = 7.8049(12) A, a =
3
˚
90°, b = 102.840(3)°, c = 908, V = 1657.1(5) A , Z = 4,
T = 293(2) K. Compound 7c crystallized in the Triclinic
˚
P-1 space group with unit cell parameters a = 7.364(2) A,
˚
˚
b = 7.366(2) A, c = 26.089(8)A, a = 87.114(7)°, b =
3
˚
87.040(7) (3)°, c = 82.337(7)°, V = 1399.2(7) A , Z = 2,
T = 293(2) K. Compound 10c crystallized in the Triclinic
˚
P-1 space group with unit cell parameters a = 9.8152(10) A,
˚
˚
b = 10.0806(13) A, c = 11.1267(14) A, a = 100.344(3)°,
3
˚
b = 111.975(3)°, c = 107.852(3)°, V = 916.18(19) A ,
Z = 2, T = 293(2) K.
Keywords 1,2,3-Triazole Á Isoxazole Á Thiadiazine Á
Oxadiazoline
Z.-Q. Dong Á F.-M. Liu (&)
College of Materials and Chemical Engineering,
Hangzhou Normal University, Hangzhou 310036,
People’s Republic of China
e-mail: fmliu859@sohu.com
Experimental Part
F.-M. Liu Á Y.-M. Zeng
All of reactions were monitored by TLC. Melting points
were determined via a mettler FP-5 melting point apparatus
College of Chemistry and Chemical Engineering, Xinjiang
University, Urumqi 830046, People’s Republic of China
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J Chem Crystallogr (2011) 41:1158–1164
1159
Compound (4a)
and were uncorrected. Elemental analyses were analysed on
a Perkin-Elmer 2400 elemental analyzer. The IR spectra
were recorded on potassium bromide pellet on a Bruker
Equinox 55 FT-IR spectrophotometer. The 1H NMR spectra
were measured by a Varian Inova-400 spectrophotometer
using TMS as an internal reference. Mass spectra were pre-
formed on an Agilent 5975 apparatus (EI, 70 eV). X-ray
diffraction data were given on a Hitachi F-4500 R-AXIS
SPIDER diffractometer. Multi-scan empirical absorption
corrections were applied to the data by using the SHEL-
XTL97 [17]. The structure was analyzed via direct methods
using SHELXTL97 and PLATON [17]. Positional and
thermal parameters were refined by the full-matrix least-
squares method on F2 using the SHELXTL97 software
package [17]. Compounds 2 [18], 3 [19], 5 [20], 6 [21], 8
[22], 9 [23] were prepared according to the literature pro-
cedure (Scheme 1).
This compound was obtained as white crystals. Yield (%),
59; mp (°C), 156–157; IR (KBr) m/cm-1: 1661 (C=O),
1631 (C=N); MS(EI) m/z (%): 316 (M?), 172, 144, 91, 77;
Anal. Calcd. (%) for C18H12N4O2: C 8.35, H 3.82, N 17.71;
Found (%): C 68.31, H 3.84, N 17.74.
Compound (4b)
White single crystals of compound 4b were obtained from
ethylacetate and petroleum ether after slow evaporation at
room temperature. Yield(%), 57; mp (°C), 152–154; IR
(KBr) m/cm-1: 1658 (C=O), 1632 (C=N); MS(EI) m/z (%):
346 (M?), 317, 172, 146, 91, 77; Anal. Calcd. (%) for
C19H14N4O3: C 65.89, H 4.07, N 16.18; Found (%): C
65.86, H 4.03, N 16.19.
Compound (4c)
General Procedure for the Preparation of (3-
Substituted-isoxazol-4-yl)-(2-phenyl-1,2,3-triazol-4-
yl)-ketones (4a–c)
This compound was obtained as yellow crystals. Yield (%),
43; mp (°C), 103–105; IR (KBr) m/cm-1: 1659 (C=O),
1631 (C=N); MS(EI) m/z (%): 352, 350 (M?), 172, 145, 91,
77; Anal. Calcd. (%) for C18H11ClN4O2: C 61.64, H 3.16;
N 15.97; Found (%): C 61.66, H 3.12, N 15.99.
To a stirred solution of the enaminone 2 (1 mmol) and the
appropriate hydroxamoyl chlorides 3 (1 mmol) in CH2Cl2
(15 mL), triethylamine (0.5 mL) was added and the mixture
was stirred at room temperature until the disappearance of
the starting materials, as monitored by TLC, was observed.
After completion of the reaction, the solution was filtered to
remove triethylamine hydrochloride, and the filtrate was
evaporated under reduced pressure. The resulting crude
product was purified by column chromatography with eth-
ylacetate:petroleum ether (1:5, v/v) as eulent to afford the
corresponding isoazole derivatives 4a–c.
General Procedure for the Preparation of 3-Substituted-
6-(2-phenyl-1,2,3-triazol-4-yl)-1,2,4-triazolo[3,4-b]-
1,3,4-thiadiazine (7a–c)
An equimolar amount of compound 5 (1 mmol) and the
appropriate 4-amino-5-mecapto-1,2,4-triazole derivatives 6
in anhydrous ethanol (10 mL) was heated under reflux for
Scheme 1 Synthesis of the
target compounds
O
C
Ar
N
N
N
ArC NOH
N
N
Ph
N
DMF-DMA
O
C
3
Ph
N
Cl
CH CHN(CH )
3 2
O
4a-c
Ar = C6H5, p-CH3OC6H4, p-ClC6H4
2
a
b
c
N
N
N
N
S
R
N
N
N
SH
N
N
R
N
N
O
Br
2
O
NH
6
2
Ph N
Ph
Ph
N
C CH
3
C
5
CH Br
2
N
7a-c
R = C6H5, p-ClC6H4, CH3CH2-
1
N
N
Ph
a
b
c
O
O
N
N
ArC NHNH
8
C
CH
2
3
Ac O
N
2
N
N
CH
3
NNHCOAr
H C
O
3
Ar
a-c
10
N
9
N
N
Ph
Ar = C6H5, p-CH3OC6H4, p-ClC6H4
a
b
c
123

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J Chem Crystallogr (2011) 41:1158–1164
6 h. After the reaction was over, the mixture was poured
into ice water. The resulting solid was collected and
crystallized from ethanol to give 7a–c.
693 (C–S–C); MS(EI) m/z (%): 311 (M?), 282, 170, 91, 77;
Anal. Calcd. (%) for C14H13N7S: C 54.00, H 4.21, N 31.49;
Found (%): C 54.03, H 4.18, N 31.46.
General Procedure for the Preparation of 2-Methyl-5-
substituted-3-acetyl-2-(2-phenyl-1,2,3-triazol-4-yl)-
1,3,4-oxadiazolines (10a–c)
Compound (7a)
This compound was obtained as white crystals. Yield (%),
67; mp (°C), 203–204; IR (KBr) m/cm-1: 1632 (C=N), 691
(C–S–C); MS(EI) m/z (%): 359 (M?), 326, 170, 91, 77;
Anal. Calcd. (%) for C18H13N7S: C 60.15, H 3.65, N 27.28;
Found (%): C 60.17, H 3.61, N 27.26.
Compound 9 (5 mmol) and 10 mL acetic anhydride was
refluxed for 2 h under stirring. The solvent was evaporated
under reduced pressure and the residue was chromato-
graphed on a silica gel column using ethylacetate:petro-
leum ether (1:3, v/v) as eulent to afford compound 10a–c.
Compound (7b)
Compound (10a)
This compound was obtained as yellow crystals. Yield (%),
63; mp (°C), 206–208; IR (KBr) m/cm-1: 1632 (C=N), 698
(C–S–C); MS(EI) m/z (%): 395, 393 (M?), 359, 170, 91,
77; Anal. Calcd. (%) for C18H12ClN7S: C 54.89, H 3.07, N
24.89; Found (%): C 54.86, H 3.04, N 24.87.
This compound was obtained as white crystals. Yield (%),
53; mp (°C), 79–81; IR (KBr) m/cm-1: 1658 (C=O), 1632
(C=N); MS(EI) m/z (%): 347 (M?), 305, 290, 172, 91, 77;
Anal. Calcd. (%) for C19H17N5O2: C 65.69, H 4.93, N
20.16; Found (%): C 65.66, H 4.91, N 20.19.
Compound (7c)
Compound (10b)
Yellow single crystals of compound 7d were obtained from
ethanol after slow evaporation at room temperature. Yield
(%), 61; mp (°C), 214–216; IR (KBr) m/cm-1: 1631 (C=N),
This compound was obtained as white crystals. Yield
(%), 62; mp (°C), 126–128; IR (KBr) m/cm-1: 1662
Table 1 Crystal data and structure refinement
Compound
4b
7c
10c
Formula
C
19H14N4O3
C14H13N7S
793845
C19H16ClN5O2
793846
CCDC
793847
Crystal color
Formula weight
Temperature (K)
Crystal size (mm)
Crystal system
Space group
Colorless
Colorless
Colorless
346.11
311.10
381.10
293(2)
293(2)
293(2)
0.58 9 0.23 9 0.17
0.64 9 0.26 9 0.16
Triclinic
0.29 9 0.27 9 0.20
Triclinic
Monoclinic
P2(1)/c
P-1
P-1
˚
a (A)
10.6974(17)
7.364(2)
9.8152(10)
10.0806(13)
11.1267(14)
100.344(3)
111.975(3)
107.852(3)
916.18(19)
2
˚
b (A)
20.356(3)
7.366(2)
˚
c (A)
7.8049(12)
26.089(8)
87.114(7)
87.040(7)
82.337(7)
1399.2(7)
2
a (°)
b (°)
c (°)
90
102.840(3)
90
3
˚
V (A )
1657.1(5)
Z
4
Dc (mg m-3
h range (°)
)
1.396
1.478
1.384
3.11–27.48°
0.099
3.13–27.48°
0.240
3.06–27.48°
0.233
l (mm-1
)
Reflections collected
15698
13621
9065
Data/restraints/parameters
Final R indices [I [ 2r(I)]
R indices (all data)
3727/0/236
6369/0/398
R1 = 0.1645, wR2 = 0.4084
R1 = 0.2384, wR2 = 0.4738
4165/0/245
R1 = 0.0710, wR2 = 0.1938
R1 = 0.1358, wR2 = 0.2992
R1 = 0.0688, wR2 = 0.1810
R1 = 0.1262, wR2 = 0.2683
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J Chem Crystallogr (2011) 41:1158–1164
1161
˚
Table 2 Selected bond lengths (A), bond angels (°) and torsion angles (°) of compounds
Compound 4b
O(1)–C(9)
C(10)–C(11)
N(1)–C(8)
1.222(3)
1.347(4)
1.333(3)
1.322(4)
1.298(4)
C(11)–O(2)–N(4)
C(12)–N(4)–O(2)
N(4)–C(12)–C(10)
C(11)–C(10)–C(12)
O(2)–C(11)–C(10)
108.0(2)
106.0(3)
111.4(3)
103.2(3)
111.4(3)
C(11)–O(2)–N(4)–C(12)
N(4)–O(2)–C(11)–C(10)
C(12)–C(10)–C(11)–O(2)
O(2)–N(4)–C(12)–C(10)
C(11)–C(10)–C(12)–N(4)
-0.8(4)
0.9(4)
-0.6(4)
0.4(4)
N(3)–C(7)
N(4)–C(12)
Compound 7c
S(1)–C(11)
S(1)–C(10)
N(3)–C(7)
0.1(4)
1.722(7)
1.792(8)
1.309(9)
1.338(8)
1.296(8)
1.368(8)
1.288(8)
1.308(9)
C(11)–S(1)–C(10)
C(9)–N(4)–N(5)
C(11)–N(5)–N(4)
C(12)–N(7)–N(6)
C(9)–C(10)–S(1)
N(6)–C(11)–N(5)
N(7)–C(12)–N(5)
N(4)–C(9)–C(10)
95.6(3)
116.6(6)
128.8(6)
107.7(6)
115.1(6)
108.8(6)
109.8(6)
125.4(6)
C(8)–N(1)–N(2)–N(3)
N(1)–N(2)–N(3)–C(7)
C(9)–N(4)–N(5)–C(11)
N(5)–N(4)–C(9)–C(10)
N(4)–C(9)–C(10)–S(1)
C(11)–S(1)–C(10)–C(9)
N(7)–N(6)–C(11)–N(5)
N(7)–N(6)–C(11)–S(1)
0.3(8)
0.0(9)
-18.8(11)
-3.3(12)
37.1(11)
-41.8(7)
-0.5(9)
N(1)–C(8)
N(4)–C(9)
N(5)–C(11)
N(7)–C(12)
N(6)–C(11)
Compound 10c
N(5)–C(13)
O(1)–C(9)
-173.4(6)
1.272(4)
1.450(4)
1.395(4)
1.374(4)
1.226(4)
1.465(4)
C(13)–O(1)–C(9)
C(13)–N(5)–N(4)
O(1)–C(9)–N(4)
N(5)–N(4)–C(9)
N(5)–C(13)–O(1)
N(4)–C(11)–C(12)
107.1(2)
104.5(3)
99.8(2)
C(9)–N(4)–N(5)–C(13)
C(13)–O(1)–C(9)–N(4)
N(5)–N(4)–C(11)–O(2)
N(4)–N(5)–C(13)–O(1)
C(6)–N(2)–N(3)–C(8)
C(13)–O(1)–C(9)–C(8)
2.2(4)
5.1(3)
N(4)–N(5)
O(1)–C(13)
O(2)–C(11)
N(4)–C(9)
-175.9(3)
1.5(4)
112.2(3)
116.1(3)
117.3(3)
177.2(3)
-111.7(3)
˚
Table 3 Intermolecular and intramolecular interactions (A) in compounds
D–H_A
D–H
H_A
D_A
D–H_A
˚
Intrarmolecular interactions (A) in the compound 4b
C(1)–H(1B)_N(1)
0.93
0.93
2.52
2.32
2.830(4)
2.879(4)
100
119
C(11)–H(10A)_N(1)
˚
Intramolecular interactions (A) in the compound 7c
C(5)–H(5A)_N(3)
0.93
2.51
2.48
2.822(9)
100
107
C(10)–H(10C)_N(1)
0.97
˚
2.909(10)
Intramolecular and intermolecular interactions (A) in the compound 10c
C(10)–H(10B)_O(2)
C(19)–H(19A)_O(1)
C(1)–H(1B)_O(2)a
C(12)–H(12A)_O(2)b
C(17)–Cl(1)_Cg(1)c
0.96
0.93
0.93
0.96
0.57
2.55
3.072(5)
2.818(5)
3.225(5)
3.385(6)
4.655(4)
114
2.50
100
2.53
132
2.43
178
3.877(2)
105.71(15)
Cg(1) is the center of gravity of ring O(1)–C(9)–N(4)–N(5)–C(13)
a
-1 - x, -1 - y, 1 - z
b
-1 - x, -y, 1 - z
c
-x, -y, -z
(C=O), 1632 (C=N); MS(EI) m/z (%): 377 (M?), 335,
320, 172, 91, 77; Anal.Calcd. (%) for C20H19N5O3: C
63.65, H 5.07, N 18.56; Found (%): C 63.63, H 5.04, N
18.53.
Compound (10c)
White single crystals of compound 10c were obtained from
ethylacetate and petroleum ether after slow evaporation at
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J Chem Crystallogr (2011) 41:1158–1164
Fig. 1 Molecular structure
of 4b
room temperature. Yield (%), 57; mp (°C), 151–153; IR
(KBr) m/cm-1: 1659 (C=O), 1631 (C=N); MS(EI) m/z (%):
383, 381 (M?), 339, 324, 172, 91, 77; Anal. Calcd. (%) for
C19H16ClN5O2: C 59.77, H 4.22, N 18.34; Found (%): C
59.74, H 4.19, N 18.31.
Results and Discussion
Synthetic Methodology
Compound 1 with DMF-DMA to give the novel enaminone
2. The reaction of the latter with various arylhydroximinoyl
chlorides afforded regioselectively the substituted isoazoles
4 in good yield, respectively. Treatment of compound 1 with
Br2 gave the intermediate 4-(2-bromoacetyl)-2-phenyl-
1,2,3-triazole 5, which condensed with 4-amino-5-mer-
capto-1,2,4-triazole derivatives afforded the corresponding
[1,2,4]triazolo[3,4-b]-[1,3,4]thiadiazine derivatives 7. Sim-
ilarly, semicarbazones 9 obtained from condensation of 1
with various carbohydrazide derivatives, cyclization of 9 in
acetic anhydride resulted in the formation of 1,3,4-
oxadiazolines 10.
Fig. 2 Packing diagram of 4b
(plane 1) in the molecular structure. All atoms are almost
coplanar due to existing mean deviations of 0.0021 and
X-Ray Analysis
˚
0.0030 A for plane 2 and plane 1, respectively. Whereas,
the structure of the whole molecule is not planar. The
central isoxazole part forms dihedral angles of 15.9° and
52.4° for plane 2 and the phenyl (plane 3) defined by C13/
C14/C15/C16/C18/C19, respectively. Besides, The plane 1
The structures of compounds 4, 7, 10 were further con-
firmed from the single crystal X-ray crystallographic
studies. All crystal datas and structure refinements are
listed in Table 1, selected length, angles and torsion angles
are tabulated in Table 2 and intramolecular and intermo-
lecular interactions are showed in Table 3.
˚
centroid lies 4.589 and 4.008 A from plane 2 and plane 3,
respectively.
In the crystal Structure, there is no classic hydrogen
bonds found, whereas weak intramolecular hydrogen bond
of C(1)–H(1)_N(1), C(11)–H(10A)_N(1) exist in the
molecular.
The crystal structure of compound 4b is showed in
Fig. 1, and a perspective view of the crystal packing in the
unit cell is showed in Fig. 2. There are two five-member
rings, 1, 2, 3-triazole ring (plane 2) and isoxazole ring
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J Chem Crystallogr (2011) 41:1158–1164
1163
Fig. 4 Packing diagram of 7c
1,2,4-triazole ring is fused to the six-membered thiadiazine
ring at N5 and C11 and includes an endocyclic double bond
at N4=C9. The double bonds N4=C9 and C8=N11 exist in
an s-tran configuration around the C8–C9 single bond due
to steric strain. Then, the six-membered thiadiazine ring
defined by S1/N4/N5/C9/C10/C11 is distorted from pla-
narity owing to atoms S1 and C10 deviating -0.2625 and
Fig. 3 Molecular structure of 7c
The crystal structure of the compound 7c was deter-
mined to create conformation of the molecule in Fig. 3 and
had provided valuable view into the effect of steric factors
on the three dimensional shape of the bicyclic ring-fused
compound 7. Crystal packing in the unit cell is showed in
Fig. 4. In the structure, the five-membered 1,2,4-triazole
and 1,2,3-triazole rings are almost coplanar due to existing
˚
0.2906 A, respectively. The thiadiazine ring separately
forms dihedral angles of 7.3° and 11.2° with 1,2,4-triazole
and 1,2,3-triazole rings. There is no classic hydrogen bonds
found, but intramolecular hydrogen bond of C(5)–
H(5A)_N(3), C(10)–H(10C)_N(1) exist in the molecular.
The crystal structure and a perspective view of the
crystal packing in the unit cell of the compound 10c are
˚
mean deviations of 0.0067 and 0.0017 A, respectively. The
Fig. 5 Molecular structure
of 10c
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J Chem Crystallogr (2011) 41:1158–1164
Acknowledgment This work was supported by the National Natural
Science Foundation of China (Nos. 20562011, 20662009).
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showed in Figs. 5 and 6, respectively. There is a five-
member ring in the molecule resulting from the cyclic
action under acetic anhydride. All atoms (O(1), C(9), N(4),
N(5), C(13)) in the ring are nearly coplanar due to these
five atoms are only slightly out of plane, existing a mean
˚
deviation of 0.0200 A, only with maximum mean plane
˚
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illuminate that the oxadiazoline and 1, 2, 3-triazole rings
are almost perpendicular owing to exiting a dihedral angle
of 94.9° each other. The acetyl plane forms a angle of 2.5°
with oxadiazoline plane. In addition, the distance of the
ˇ
12. Japelj B, Recnik S, Cebasek P, Stanovnik B, Svete J (2005)
J Heterocyclic Chem 42:1167
˚
oxadiazoline plane centroid lies 3.439 A from 1, 2, 3-tri-
azole plane. In the crystal Structure, there is no classic
hydrogen bonds found, thus, the structure is leveled off
by some weak C–H_O intermolecular hydrogen bonds.
Whereas molecular can be further stabilized via weak
intermolecular C–Cl_Cg (p-ring) interactions that were
listed in Table 3, providing assist for molecular packing
stability in the unit cell. The most noteworthy intermo-
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˚
lecular interaction is a Cl_Cl contact of length 3.495(2) A
(1 - x, -y, -z) in Fig. 6.
CCDC-793846\793845\793847 contains the supple-
mentary crystallographic datas for this paper. These datas
can be obtained free of charge from the Cambridge Crys-
tallographic Data Centre (CCDC) via e-mail: deposit@ccdc.
cam.ac.uk.
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In conclusion, we have gained a series of new hetero-
cyclic compounds bearing 1,2,3-triazole moiety which
were synthesized via using 4-acetyl-2-phenyl-1,2,3-triazole
1 as the starting material.
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123