Traceless sulfone linker for the solid-phase organic synthesis of 1-(E)-styryl-4-substituted-1,2,3-triazoles

Article abstract of DOI:10.1080/00397911.2012.744056

A novel, facile, solid-phase, organic synthesis of 1-(E)-styryl-4- substituted-1,2,3-triazoles in good yields and purities via traceless sulfone linker has been developed. Key steps involved in this synthetic procedure include (i) sulfone alkylation of su

Full text of DOI:10.1080/00397911.2012.744056

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Traceless Sulfone Linker for the Solid-
Phase Organic Synthesis of 1-(E)-
Styryl-4-substituted-1,2,3-triazoles
Jian-Wen Jiang a , Shou-Ri Sheng a , Xiao-Lan Zhang b , Zheng Fang a
& Ming-Zhong Cai a
a College of Chemistry and Chemical Engineering, Jiangxi Normal
University , Nanchang , China
b Department of Chemistry , Shangrao Normal College , Shangrao ,
China
Published online: 08 Jul 2013.
To cite this article: Jian-Wen Jiang , Shou-Ri Sheng , Xiao-Lan Zhang , Zheng Fang &
Ming-Zhong Cai (2013) Traceless Sulfone Linker for the Solid-Phase Organic Synthesis of
1-(E)-Styryl-4-substituted-1,2,3-triazoles, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 43:20, 2784-2792, DOI:
10.1080/00397911.2012.744056
To link to this article: http://dx.doi.org/10.1080/00397911.2012.744056
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Synthetic Communications1, 43: 2784–2792, 2013
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2012.744056
TRACELESS SULFONE LINKER FOR THE
SOLID-PHASE ORGANIC SYNTHESIS OF 1-(E)-
STYRYL-4-SUBSTITUTED-1,2,3-TRIAZOLES
Jian-Wen Jiang,1 Shou-Ri Sheng,1 Xiao-Lan Zhang,2
Zheng Fang,1 and Ming-Zhong Cai1
1College of Chemistry and Chemical Engineering, Jiangxi Normal University,
Nanchang, China
2Department of Chemistry, Shangrao Normal College, Shangrao, China
GRAPHICAL ABSTRACT
Abstract A novel, facile, solid-phase, organic synthesis of 1-(E)-styryl-4-substituted-1,2,3-
triazoles in good yields and purities via traceless sulfone linker has been developed. Key
steps involved in this synthetic procedure include (i) sulfone alkylation of sulfinate resin
with (2-azido-1-iodoethyl)benzene, (ii) [3 þ 2] cycloaddition with terminal alkynes in
the presence of CuI, and (iii) traceless product release by base-mediated elimination
process.
Keywords Click chemistry; 1,4-disubstituted-1,2,3-triazole; elimination reaction;
1-(E)-styryl substituent; solid-phase organic synthesis; sulfone linker
INTRODUCTION
Combinatorial chemistry, together with the solid-phase organic synthesis
(SPOS) technique, has been employed as an efficient methodology for the high-speed
synthesis of structurally diverse compounds for the drug discovery community.[1] The
SPOS approach provides many advantages in terms of separation and purification of
materials and unique opportunities in controlling organic reactions.[2] 1,2,3-Triazoles
are some of the most useful heterocycles[3] and have been widely used in many
research fields such as materials, chemical, and biological sciences.[4] Because of their
Received August 18, 2012.
Address correspondence to Shou-Ri Sheng, College of Chemistry and Chemical Engineering,
Jiangxi Normal University, Nanchang 330022, China
2784

SPOS OF 1-(E)-STYRYL-1,2,3-TRIAZOLES
2785
importance, the synthesis of 1,2,3-triazoles from various azides and alkynes has been
widely studied in solution phase.[5,6] Nevertheless, among them, little attention has
been paid to the preparation of styryl-substituted 1,2,3-triazoles.[7] To our knowledge,
only a few papers have reported the solid-phase synthesis of 1,2,3-triazoles up to
now.[8] Moreover, there are no reported examples involving the SPOS of styryl-
substituted 1,2,3-triazoles. Therefore, the development of a versatile SPOS procedure
toward functionalized 1,2,3-triazoles containing the styryl moiety is still in demand. It
is well known that the sulfonyl group is an important activating moiety introduced in
an intermediate molecule for the construction of carbon–carbon bonds and other
transformations.[9] The sulfonyl group is readily converted to a leaving group, making
a carbon–carbon double bond via a base-promoted b-elimination route.[10] Further-
more, sulfinate-functionalized resins have been developed efficiently and utilized in
SPOS, and the resulting sulfone linker has been found to be both a robust and a
[8h,14–16]
[17]
versatile linker.[11–13] Recently, several research groups,
including ours,
have been interested in the development of sulfone-linking strategies for SPOS meth-
ods to explore sulfone-based chemical transformations. As a part of our ongoing
research program focused on the use of a versatile traceless sulfone linker in SPOS,
we herein present an efficient solid-phase synthetic approach for the preparation of
1-(E)-styryl-4-substituted-1,2,3-triazoles, as shown in Scheme 1.
As outlined in Scheme 1, polystyrene=1% divinylbenzene sodium sulfinate resin
(1) was allowed to react with (2-azido-1-iodoethyl)benzene[18] in dimethylfor mamide
(DMF) in the presence of tetrabutylammonium iodide (NBu4I) and potassium iodide
to afford polymer-supported (2-azido-1-phenyl)ethyl sulfone (2) in excellent yield
(>95%, determined by elementary analysis of the nitrogen–azide
loading ¼ 1.55 mmol=g), which was amenable to Fourier transform infrared (FTIR)
monitoring for the complete disappearance of the sulfinate stretch at 960 cmꢀ1 and
appearance of a characteristic azido band at 2098 cmꢀ1, as well as the two typical
sulfone stretches (nasym ¼ 1305 cmꢀ1 and nsym ¼ 1145 cmꢀ1).
With resin 2 in hand, [3 þ 2] cycloaddition reaction of 2 with various terminal
alkynes, the key for the success of this protocol was then investigated. It has been
reported that the copper-catalyzed alkyne–azide cycloaddition (CuAAC) is a reliable
means for the synthesis of 1,4-disubstituted-1H-1,2,3-triazoles exclusively.[5,6] Based
on these results, phenylacetylene was chosen for the template reaction with 2. To
Scheme 1. Solid-phase synthetic route to 1-(E)-styryl-4-substituted-1,2,3-triazoles.

2786
J.-W. JIANG ET AL.
optimize reaction conditions, several solvents such as tetrallydrofuran (THF),
MeCN, demethylformamide (DMF), chimethylsulfoxide (DMSO), t-BuOH,
CH2Cl2, and their cosolvents were tested in the same standard reaction in the pres-
ence of catalyst (CuSO4=sodium ascorbate or CuI). After a considerable number of
experiments, the 1,3-dipolar cycloaddition of 2 with phenylacetylene was conducted
smoothly in DMF=THF (1=2) in the presence of diisopropylethylamine (DIPEA),
triphenyl phosphine (Ph3P), and 10 mol% of CuI at room temperature for 12 h, lead-
ing to the polymer-supported (1-phenyl-2-triazolyl)ethyl sulfone (3a). It should be
point out that the FTIR spectrum of 3a also showed the sulfone stretches at 1308
and 1147 cmꢀ1, which were quite similar to the values of resin 2 (sulfone absorption
bond at 1305 and 1145 cmꢀ1). Obviously, this transformation (conversion of 2 to 3a)
could not be reliably monitored only by FTIR spectroscopy for the appearance
of sulfonyl stretch bands. However, interestingly, this transformation seemed to be
quantitative, because no characteristic azido absorption at 2098 cmꢀ1 could be
detected in the FTIR spectrum of 3a after completing this cycloaddition reaction.
In the progress of this transformation, it was found that the signal of the azido group
(2098 cmꢀ1) has distinctly shrunk after 8 h of reaction time, and another 4 h of reac-
tion time leading to a complete disappearance of the characteristic azido absorption.
Subsequently, base-mediated b-elimination cleavage conditions of resin 3a for
liberating the target molecule 1-styryl-4-phenyl-1H-1,2,3-triazole (4a) was examined.
After various reaction conditions were evaluated by varying reaction time, tempera-
ture, base, and solvent, such as Et3N=CH2Cl2, DBU=CH2Cl2, CH3ONa=CH2Cl2,
and t-BuOK=THF, the best results were obtained by treating resin 3a with
CH3ONa=CH3OH in CH2Cl2 at room temperature for 4 h. In the FTIR spectrum
of the residue resin, no sulfone absorption peaks were observed, indicating this cleav-
age step was complete. Fortunately, without further purification, the crude product
4a was obtained in high purity (96%, indicating by high-performance liquid chromo-
tography [HPLC] analysis) after removal of excess cleavage reagent and evaporation
of residual solvent. Then passing the crude product through a flash silica-gel column
chromatography eluted with ethyl acetate=hexane afforded pure target compound 4a
in 90% yield based on the loading of starting resin 1 (Table 1, entry 1).
Table 1. The yields and purities of 1-(E)-styryl-4-substituted-1H-1,2,3-triazoles (4a–4i)
Yielda
(%)
Purityb
(%)
Entry
R
Product
1
2
3
4
5
6
7
8
9
C6H5
4a
4b
4c
4d
4e
4f
90
90
88
87
85
84
86
84
85
96
96
95
98
95
97
96
97
98
4-CH3CH2C6H4
2-CH3C6H4OCH2
2-CH3OC6H4OCH2
2-NO2C6H4OCH2
4-NO2C6H4OCH2
2-ClC6H4OCH2
2-Naphthoxymethyl
n-C4H9
4g
4h
4i
aOverall isolated yields based on polystyrene-supported sodium sulfinate 1 (2. 0 mmol =g).
bDetermined by HPLC of crude cleavage product (k ¼ 254 nm).

SPOS OF 1-(E)-STYRYL-1,2,3-TRIAZOLES
2787
To test the scope of the protocol, a variety of 1-styryl-4-substituted-1H-
1,2,3-triazoles (4a–4i) were prepared from different terminal alkynes with resin 2
under the optimized conditions. As seen from Table 1, both aromatic and aliphatic
alkynes underwent the reaction smoothly to afford the corresponding products 4a–
4i in good to excellent yields (84–90%) with excellent purities (95–98%). It is
noteworthy that all target compounds were formed with complete (E) stereoselectiv-
ities, which were confirmed by the coupling constants of the olefinic protons in their
NMR spectra. For instance, in the 1H NMR spectrum of 1-(E)-styryl-4-(4-
nitrophenoxymethyl)-1H-1,2,3-triazole (4f), the coupling constants (J ¼ 14.8 Hz)
between the two olefinic protons at d ¼ 7.77 and 7.22 ppm were observed, which indi-
1
cated exclusive production of E-isomer. Additionally, the H NMR spectrum of 4f
exhibited a distinct singlet at d ¼ 7.99 ppm for the triazolyl C5–H proton, and its
ꢀ1
=
IR spectrum displayed C C olefin absorption at 1655 cm and characteristic band
at 1509 cmꢀ1, indicating the presence of a nitro group. It should be pointed out that
the analogous 1-styryl-1,2,3-triazoles with substituents in the benzene ring can also be
prepared using the present method. For example, when using 1-(2-azido-
1-iodoethyl)-4-methylbenzene in place of (2-azido-1-iodoethyl)benzene, together with
phenylacetylene as a reaction substrate, the corresponding target molecule, 1-(E)-
(4-methylstyryl)-4-phenyl-1H-1,2,3-triazole (4a0) was obtained in 88% yield.
In summary, a facile protocol for the solid-phase synthesis of 1-(E)-styryl-
4-substituted-1H-1,2,3-triazoles has been developed based on traceless sulfone lin-
ker. Simple workup, mild reaction conditions, and good to excellent yields make this
methodology attractive and suitable for combinatorial library production.
EXPERIMENTAL
Melting points were determined on an X4 melting-point apparatus and are uncor-
rected.1H and 13C NMR spectra were recorded on a Bruker Avance (400-MHz) spec-
trometer, using CDCl3 as the solvent and TMS as an internal standard. FTIR spectra
were taken on a Perkin-Elmer SP One FTIR spectrophotometer. Microanalyses were
performed with a Carlo Erba 1106 elemental analyzer. High-performance liquid chro-
matography (HPLC) analysis was performed on Agilent 1100 automated system having
a photodiode array (PDA) detector (k
¼ 254 nm used for this study). Polystyrene=
max
1% divinylbenzene sodium sulfinate (2.0mmol –SO2Na=g) was purchased from Tianjin
Nankai Hecheng Science and Technology Co. (100–200 mesh). (2-Azido-1-iodoethyl)-
benzene [18] was prepared according to the procedure in the literature. Terminal alkynes
(3c–3h) were prepared by alkylation of the corresponding phenols with propargyl bro-
mide in the presence of K2CO3 in acetone under refluxing conditions using a method
similar to that described in the literature.[19] The terminal alkynes (3a, 3b, and 3i) and
other chemicals were obtained from commercial suppliers (Aldrich, USA, and Shanghai
Chemical Company, China) and used without purification prior to use. All organic
solvents were dried by standard methods.
Preparation of Polymer-Supported (2-Azido-1-phenyl)ethyl Sulfone (2)
Resin 1 (2.0 g, 3.6 mmol) was swollen in a mixture of DMF (20 mL) by
gently shaking the resin–DMF mixture at room temperature for 30min. Then

2788
J.-W. JIANG ET AL.
(2-azido-1-iodoethyl)benzene (5.0 mmol), tetrabutylammonium iodide (1.0 mmol), and
potassium iodide (5.0 mmol) were added to this mixture, and the resulting reaction mix-
ture was shaken at room temperature under a nitrogen atmosphere for 24 h. After fil-
tration, the resin was washed successively with DMF, H2O, CH3OH, and Et2O
(2ꢁ 10 mL of each) and then dried under reduce pressure over phosphorous pentoxide
at 50–60ꢂC to afford resin 2 as yellow beads (azide loading ¼ 1.55mmol=g). IR (KBr):
n ¼ 3061, 3030, 2934, 2098, 1583, 1498, 1448, 1304, 1292, 1145, 1082, 915, 811, 762cmꢀ1
.
General Procedure for the Synthesis of 1-(E)-Styryl-
4-substituted-1H-1,2,3-triazoles (4a–4i)
Alkyne (3.0 mmol), CuI (191 mg, 10 mol%), DIPEA (0.4 mL, 500 mol%), and
Ph3P (262 mg, 10 mol%) were added to the suspension of the resin 2 (645 mg,
1.0 mmol) preswollen in DMF =THF (1:2, 15 mL) and then shaken at room tempera-
ture for 12 h. The resin was collected by filtration; washed with pyridine, CH2Cl2,
THF, and Et2O (2 ꢁ 10 mL of each); and dried under vacuum overnight to yield resin
3a–3i. Subsequently, after resin 3a–3i was swollen in a mixture of THF (10 mL) and
CH3OH (5 mL) for 1 h, sodium methoxide (0.16 g, 3.0 mmol) was added to the suspen-
sion and then shaken at room temperature for 4 h. The resin was filtered and washed
with THF=H2O (1=1), THF, and Et2O (2 ꢁ 10 mL of each). Evaporation of the solvent
from the filtrate afforded crude product 4a–4i with more than 95% purity determined
by HPLC, which was further purified by flash silica-gel column chromatography and
eluted with ethyl acetate=hexane to provide pure product 4a–4i for structures analysis.
1-(E)-Styryl-4-phenyl-1H-1,2,3-triazole (4a). Pale yellow viscous oil; 1H
NMR (400 MHz, CDCl3): d ¼ 7.79–7.77 (m, 2 H), 7.72 (s, 1 H), 7.42–7.32 (m, 8
H), 5.80 (s, 1 H), 5.48 (s, 1 H); 13C NMR (100 MHz, CDCl3): d ¼ 146.6, 142.0,
133.7, 129.2, 128.9, 128.0, 127.8, 127.4, 126.4, 124.8, 118.8, 108.4; IR (film):
n ¼ 3061, 2925, 2854, 1644, 1577, 1456, 1429, 1267, 1233, 1074, 1021, 898, 808,
763, 692 cmꢀ1. Anal. calcd. for C16H13N3: C, 77.71; H, 5.30; N, 17.00. Found: C,
77.66; H, 5.36; N 17.05.
1-(E)-Styryl-4-(4-ethylphenyl)-1H-1,2,3-triazole (4b). Pale yellow viscous
1
oil; H NMR (400 MHz, CDCl3): d ¼ 7.90 (s, 1 H), 7.71–7.68 (m, 2 H), 7.41–7.29
(m, 5 H), 7.19–7.12 (m, 2 H), 5.78 (s, 1 H), 5.47 (s, 1 H), 2.60 (q, J ¼ 7.2 Hz, 2 H),
1.20 (t, J ¼ 7.2 Hz, 3 H); 13C NMR (400 MHz, CDCl3): d ¼ 147.7, 144.6, 143.1,
134.7, 129.9, 128.9, 128.4, 127.7, 127.4, 125.8, 119.5, 109.3, 28.7, 15.5; IR (film):
n ¼ 3028, 2964, 2928, 1642, 1496, 1445, 1265, 1230, 1017, 896, 839, 800, 772,
693 cmꢀ1. Anal. calcd. for C18H17N3: C, 78.52; H, 6.22; N, 15.26. Found: C,
78.47; H, 6.27; N, 15.32.
1-(E)-Styryl-4-(2-methylphenoxymethyl)-1H-1,2,3-triazole (4c). Pale yel-
1
low solid, mp 129–130 ꢂC; H NMR (400 MHz, CDCl3): d ¼ 7.90 (s, 1 H), 7.77 (d,
J ¼ 14.4 Hz, 1 H), 7.48 (d, J ¼ 7.2 Hz, 2 H), 7.41–7.32 (m, 3 H), 7.19–7.13 (m, 3
H), 6.97 (d, J ¼ 8.4 Hz, 1 H), 6.92 (d, J ¼ 14.4 Hz, 1 H), 5.28 (s, 2 H), 2.04 (s, 3
H); 13C NMR (400 MHz, CDCl3): d ¼ 156.4, 145.2, 133.5, 130.8, 129.0, 128.9,
127.0, 126.9, 126.8, 123.0, 122.1, 121.1, 120.0, 111.5, 62.2, 16.3; IR (KBr):
n ¼ 3136, 3096, 2927, 1655, 1493, 1454, 1383, 1350, 1239, 1050, 1021, 950, 752 cmꢀ1
.

SPOS OF 1-(E)-STYRYL-1,2,3-TRIAZOLES
2789
Anal. calcd. for C18H17ON3: C, 74.20; H, 5.88; N, 14.42. Found: C, 74.16; H, 5.93;
N, 14.38.
1-(E)-Styryl-4-(2-methoxyphenoxymethyl)-1H-1,2,3-triazole (4d). White
solid, mp 123–124 ꢂC; 1H NMR (400 MHz, CDCl3): d ¼ 7.96 (s, 1 H), 7.75 (d,
J ¼ 14.8 Hz, 1 H), 7.47 (d, J ¼ 7.6 Hz, 2 H), 7.41–7.31 (m, 3 H), 7.15 (d, J ¼ 14.8 Hz,
Hz, 1 H), 7.07 (d, J ¼ 7.6 Hz, 1 H), 6.97–6.88 (m, 3 H), 5.35 (s, 2 H), 3.88 (s, 3 H); 13
C
NMR (400 MHz, CDCl3): d ¼ 149.6, 147.5, 144.8, 133.5, 129.0, 128.8, 126.8, 122.9,
122.0, 121.9, 120.9, 120.3, 114.3, 111.9, 63.1, 55.9; IR (KBr): n ¼ 3153, 3115, 2953,
1654, 1590, 1570, 1503, 1465, 1456, 1439, 1393, 1359, 1325, 1288, 1251, 1177,
1123, 1054, 1026, 1010, 956, 875, 750 cmꢀ1. Anal. calcd. for C18H17O2N3: C,
70.34; H, 5.58; N, 13.67. Found: C, 70.27; H, 5.52; N, 13.72.
1-(E)-Styryl-4-(2-nitrophenoxymethyl)-1H-1,2,3-triazole (4e). Pale yellow
1
solid, mp 134–135 ꢂC; H NMR (400 MHz, CDCl3): d ¼ 8.04 (s, 1 H), 7.87 (dd,
J ¼ 8.0, 1.2 Hz, 1 H), 7.76 (d, J ¼ 14.8 Hz, 1 H), 7.58–7.54 (m, 1 H), 7.48 (d,
J ¼ 7.2 Hz, 2 H), 7.41–7.30 (m, 4 H), 7.22 (d, J ¼ 14.8 Hz, 1 H), 7.10–7.06 (m, 1
H), 5.42 (s, 2 H); 13C NMR (400 MHz, CDCl3): d ¼ 151.4, 143.6, 140.2, 134.3,
133.4, 129.0, 128.8, 126.8, 125.7, 122.8, 122.4, 121.2, 120.7, 115.4, 63.7; IR (KBr):
n ¼ 3071, 2957, 1658, 1606, 1517, 1347, 1275, 1251, 1168, 1044, 993, 957, 862, 775,
750, 693 cmꢀ1. Anal. calcd. for C17H14O3N4: C, 63.35; H, 4.38; N, 17.38. Found:
C, 63.40; H, 4.44; N, 17.43.
1-(E)-Styryl-4-(4-nitrophenoxymethyl)-1H-1,2,3-triazole (4f). Pale yellow
1
solid, mp 149–150 ꢂC; H NMR (400 MHz, CDCl3): d ¼ 8.22–8.19 (m, 2 H), 7.99
(s, 1 H), 7.77 (d, J ¼ 14.8 Hz, 1 H), 7.48 (d, J ¼ 7.6 Hz, 2 H), 7.42–7.33 (m, 3 H),
7.22 (d, J ¼ 14.8 Hz, 1 H), 7.11–7.07 (m, 2 H), 5.36 (s, 2 H); 13C NMR (400 MHz,
CDCl3): d ¼ 163.0, 143.1, 141.9, 133.3, 129.0, 128.8, 126.8, 126.0, 122.7, 122.6,
120.6, 114.9, 62.3; IR (KBr): n ¼ 3080, 2930, 2875, 1655, 1607, 1591, 1509, 1495,
1459, 1348, 1297, 1249, 1176, 1153, 1113, 1048, 1018, 1006, 951, 868, 846, 751,
696 cmꢀ1. Anal. calcd. for C17H14O3N4: C, 63.35; H, 4.38; N, 17.38. Found: C,
63.31; H, 4.43; N, 17.44.
1-(E)-Styryl-4-(2-chlorophenoxymethyl)-1H-1,2,3-triazole (4g). Pale yel-
1
low solid, mp 106–108 ꢂC; H NMR (400 MHz, CDCl3): d ¼ 7.98 (s, 1 H), 7.76 (d,
J ¼ 14.8 Hz, 1 H), 7.47 (d, J ¼ 7.2 Hz, 2 H), 7.41–7.32 (m, 4 H), 7.26–7.19 (m, 2
H), 7.15 (d, J ¼ 15.6 Hz, 1 H), 6.92–6.89 (m, 1 H), 5.34 (s, 2 H); 13C NMR
(400 MHz, CDCl3): d ¼ 153.7, 144.4, 133.5, 130.4, 129.0, 128.9, 127.9, 126.8, 123.2,
122.9, 122.2, 120.3, 116.2, 114.3, 63.4; IR (KBr): n ¼ 3104, 3086, 2931, 1654, 1587,
1485, 1388, 1350, 1242, 1161, 1133, 1049, 1018, 969, 856, 750 cmꢀ1. Anal. calcd.
for C17H14ClON3: C, 65.49; H, 4.53; N, 13.48. Found: C, 65.42; H, 4.58; N, 13.52.
1-(E)-Styryl-4-(2-naphthoxymethyl)-1H-1,2,3-triazole (4h). White solid,
1
mp 158–160 ꢂC; H NMR (400 MHz, CDCl3): d ¼ 7.97 (s, 1 H), 7.97–7.74 (m, 4
H), 7.48–7.44 (m, 3 H), 7.40–7.34 (m, 5 H), 7.23–7.20 (m, 1 H), 7.19 (d, J ¼ 14.8 Hz,
Hz, 1 H), 5.40 (s, 2 H); 13C NMR (400 MHz, CDCl3): d ¼ 156.1, 144.6, 134.4, 133.5,
129.7, 129.2, 129.1, 128.9, 127.7, 126.9, 126.8, 126.6, 124.0, 122.9, 122.1, 120.1, 118.7,
107.3, 62.0; IR (KBr): n ¼ 3055, 2917, 1658, 1627, 1599, 1511, 1461, 1390, 1260, 1218,

2790
J.-W. JIANG ET AL.
1183, 1119, 1043, 951, 837, 818, 749, 694 cmꢀ1. Anal. calcd. for C21H17ON3: C,
77.04; H, 5.23; N, 12.84. Found: C, 77.00; H, 5.28; N, 12.90.
1-(E)-Styryl-4-(N-Butyl)-1H-1,2,3-triazole (4i). Colorless oil; 1H NMR
(400 MHz, CDCl3): d ¼ 7.98 (s, 1 H), 7.75 (d, J ¼ 14.8 Hz, 1 H), 7.42–7.38 (m, 2
H), 7.34–7.27 (m, 3 H), 7.15 (d, J ¼ 14.8 Hz, 1 H), 2.70 (t, J ¼ 7.2 Hz, 2 H),
1.68–1.60 (m, 2 H), 1.41–1.39 (m, 2 H), 0.98 (t, J ¼ 7.6 Hz, 3 H); 13C NMR
(400 MHz, CDCl3): d ¼ 147.2, 135.9, 133.9, 128.7, 128.1, 126.9, 125.7, 118.8, 32.3,
26.0, 22.6, 14.1; IR (neat): n ¼ 3050, 2923, 1655, 1625, 1600, 1464, 1390, 1263,
1222, 1180, 1119, 1040, 950, 835, 750, 695 cmꢀ1. Anal. calcd. for C14H17N3: C,
73.98; H, 7.54; N, 18.49. Found: C, 73.92; H, 7.61; N, 18.53.
1-(E)-(4-Methylstyryl)-4-phenyl-1H-1,2,3-triazole (4a’). White solid, mp
88–89 ꢂC; 1H NMR (400 MHz, CDCl3): d ¼ 7.92 (s, 1 H), 7.70–7.65 (m, 2 H),
7.42–7.30 (m, 5 H), 7.12 (d, J ¼ 7.8 Hz, 2 H), 5.81 (s, 1 H), 5.50 (s, 1 H), 2.31 (s, 3
H); 13C NMR (100 MHz, CDCl3): d ¼ 147.4, 138.2, 133.5, 132.2, 130.3, 129.3,
128.7, 128.0, 126.8, 126.5, 125.6, 117.7, 21.2; IR (film): n ¼ 3058, 2927, 2856, 1640,
1450, 1430, 1377, 1265, 1231, 1075, 1020, 895, 821, 765, 690 cmꢀ1. Anal. calcd. for
C17H15N3: C, 78.13; H, 5.79; N, 16.08. Found: C, 78.03; H; 5.86; N, 16.14.
ACKNOWLEDGMENTS
We gratefully acknowledge financial support from the National Natural
Science Foundation of China (No. 21062007) and the Research Program of Jiangxi
Province Department of Education (Nos. GJJ10385, GJJ10733, and GJJ11380).
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