Synthesis, characterisation and photophysical properties of a,a-diaryl-acrylonitrile derivatives

Article abstract of DOI:10.3184/030823409X460687

a,b-Diarylacrylonitrile derivatives can be prepared by two different routes: (1) the intermolecular condensation of the same arylacetonitriles (2) the condensation of arylaldehydes and arylacetonitriles with a catalytic amount of NaOCH₃ at room temperature. Several a,b-diarylacrylonitrile derivatives have been synthesised in this paper and characterised. The UV-vis absorption and photoluminescent (PL) spectra of the products were investigated.

Full text of DOI:10.3184/030823409X460687

JOURNAL OF CHEMICAL RESEARCH 2009
JUNE, 377–380
RESEARCH PAPER 377
Synthesis, characterisation and photophysical properties of
α,β-diaryl-acrylonitrile derivatives
Youfeng Yue, Haiyan Fang, Meijun Wang, Zhiyuan Wang and Mingxin Yu*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P.R. China
a,b-Diarylacrylonitrile derivatives can be prepared by two different routes: (1) the intermolecular condensation of
the same arylacetonitriles (2) the condensation of arylaldehydes and arylacetonitriles with a catalytic amount of
NaOCH3 at room temperature. Several a,b-diarylacrylonitrile derivatives have been synthesised in this paper and
characterised. The UV-vis absorption and photoluminescent (PL) spectra of the products were investigated.
Keywords: arylacetonitrile, arylaldehyde, a,b-diarylacrylonitrile, intermolecular condensation, photophysical property
The biaryl unit is a useful group in many classes of natural
products1,2 and a,b-diarylacrylonitriles are of considerable
economic interest since nitriles serve as versatile intermediates
in the synthesis of variety of products such as perfumes, sex
pheromones, vitamin A and pigments.3,4 Many approaches to
synthesis of these compounds have been reported.2-10 Niederl
and Ziering described the synthesis and estrogenic character
of a number of alkoxy cyanostilbenes.5 John and co-workers
reported the direct conversion of carbonyl compounds into a,
b-unsaturated nitriles in the presence of nitriles.6 Russel and
Hunziker studied the condensation of substituted phenylacetic
acids and aromatic aldehydes in refluxing acetic anhydride
in the presence of triethylamine.8 Furthermore, a mild and
efficient route to prepare phenanthrane derivatives using
an intramolecular biaryl oxidative coupling of stilbenes
by vanadium oxytrichloride was reported by Huang and
coworkers.2 Motokura et al studied ruthenium-grafted
hydrotalcite as a multifunctional catalyst for the direct a-
alkylation of nitriles with primary alcohols.9 Buskley and
Rapoport reported the condensation of nitriles and aldehydes
using NaOEt at reflux in ethanol.10 However, in previous
syntheses of diarylacrylonitriles, either a base and solvent or
expensive reagents were used.
Table 1 Products, conditions and yields of the reactions
Entry R1
R2
R3
R4
Temp. Time Yielda
/°C
/h
/%
2a
2b
2c
2c
2d
2d
2b
2c
2d
2e
2f
2g
2h
2i
2j
2k
2l
OMe OMe
OMe OMe
Reflux
Reflux
r.t.
Reflux
r.t.
20
6
6
6
6
6
2
1
1
2
1
2
2
3
1
1
2
2
1
82b
50b
70b
30b
45b
20b
92c
95c
97c
94c
97c
93c
94c
92c
94c
95c
94c
95c
90c
H
H
H
H
H
H
H
H
OMe
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
OMe
H
H
H
Cl
Cl
OMe
H
Cl
Cl
Cl
Reflux
r.t.
OMe
H
r.t.
Cl
r.t.
OMe OMe
H
r.t.
H
H
H
Cl
OMe
H
H
r.t.
H
r.t.
OMe
OMe
OMe
Cl
r.t.
OMe OMe
r.t.
H
H
Cl
H
r.t.
r.t.
OMe OMe
Cl
r.t.
2m
2n
H
H
OMe
NO2
Cl
r.t.
H
r.t.
aIsolated yields; bMethod 1; cMethod 2.
The condensation of arylaldehydes and arylacetonitriles
gives a,b-diarylarylonitrile derivatives with NaOCH3 in
ethanol. The results are shown in Scheme 2 and Table 1. The
products were obtained in high to quantitative yields in short
reaction times compared to the first method.
All products were obtained as single stereoisomers, and
identified using IR, 1H NMR, 13C NMR, mass spectra
and elemental analysis as appropriate. The formation of a
single (Z)-isomer was established by TLC and 1H NMR
measurements.
In our previous work, we studied the synthesis and
photophysical properties of some tertiary arylamines.11-15 We
now report two different synthetic routes to a, b-diarylarylo-
nitrile derivatives and their photophysical properties.
Under optimised conditions, arylacetonitriles undergo
intermolecular condensation in the presence of NaNH2 giving
a,b-diarylarylonitrile derivatives (see Scheme 1). We have
found that 3,4-dimethoxyphenylacetonitrile and 4-methoxy-
phenylacetonitrile can form diarylacrylonitriles at reflux
temperture in toluene, but reaction does not take place at room
temperature.Phenylacetonitrileand4-chlorophenylacetonitrile
give diarylacrylonitriles at room temperature while the yields
of the products were very poor at reflux temperature as
demonstrated in Table 1.
Further experiments on preparation of such derivatives are
shown in Scheme 3 and Table 2. Naphthaldehyde replaced
benzaldehyde and reacted with arylacetonitriles to afford
several new compounds.
R1
R2
CN
R1
R1
CN
2.2 eq NaNH2
Toluene
R2
R2
2a-d
R1 = OMe; H; R2 = OMe, H, Cl
Scheme 1
* Correspondent. E-mail: mingxinyu@css.zju.edu.cn

378 JOURNAL OF CHEMICAL RESEARCH 2009
R3
R4
CN
R1
R2
R3
R4
CHO
10 %mol NaOCH3
EtOH, r.t.
CN
+
R1
R2
H
2b-n
R1 =OMe, H; R2 =OMe, H, Cl, NO2
R3 =OMe, H; R4 =OMe, H, Cl
Scheme 2
CHO
CN
CN
10% mol NaOCH3
+
H
EtOH, r.t.
X
X
X= H; p-Cl, p-Br, p-NO2; m-NO2
3a-e
CN
CHO
CN
10% mol NaOCH3
+
H
EtOH, r.t.
X
X
X= H; p-Cl, p-Br, p-NO2; m-NO2
3f-j
Scheme 3
In order to investigate their photophysical properties, the
UV-vis and photoluminescent (PL) spectra of compounds
in CH2Cl2 solution and the solid state were recorded. The
spectroscopic data are summarised in Tables 3 and 4.
The lowest UV-vis absorption maxima in CH2Cl2 solution
appear in the region of 315–369 nm and are assigned to the
π–π* transitions of the compounds. All these compounds
emit light strongly in the solution and in the solid state. They
exhibit emission with lmax in the range of 390–490 nm in
CH2Cl2 and 399–529 nm in the solid state. The emission peaks
of the compounds in the solid state show red shifts 10–80 nm
from the peaks in CH2Cl2 solution except for 2k, indicating
intermolecular interactions in their solid states.
Table 3 Photophysical properties of compounds (2a–n)
Entry
almaxabs/nm
blmaxem/nm
clmaxem/nm
2a
2b
2c
2d
2e
2f
2g
2h
2i
2j
2k
2l
2m
2n
360,226
441
426
390
398
445
395
414
420
440
443
458
448
421
430
500
468
399
431
463
438
470
432
468
527
410
471
439
437
346,239
315,232
323,236
345,275,240
319,233
322,236
323,238
352,242,227
343,239
323,235
353,280,241
339,238
338,227
As Table 4 shows, replacement of the H atom in 3a by a
more powerful electron-acceptor group, such as Cl, Br and
NO2, gives compounds (3b, 3c, 3d, 3e), which have emission
at much longer wavelengths. The compound (3i) shows a
considerable red-shift with emission at 518 nm.
aMaximum absorption wavelength in CH2Cl2 solution;
bMaximum emission wavelength in CH2Cl2 solution; cMaximum
emission wavelength in the solid state.
Table 4 Photophysical properties of compounds (3a–j)
Entry
almaxabs/nm
blmaxem/nm
clmaxem/nm
Table 2 Reaction conditions and yields of a,b-diarylacrylo-
nitrile derivatives (3a–j)
3a
3b
3c
3d
3e
3f
3g
3h
3i
341,232
420
431
437
464
456
412
420
418
490
453
481
498
484
529
497
432
423
424
518
500
Entry
X
Time/h
Yield/%
345,232
348,231
3a
3b
3c
3d
3e
3f
H
2
1
82
88
90
89
87
86
90
88
91
89
369,297,232
350,296,232
334,281,241
338,282,242
336,282,243
353,264,237
330,279,232
p-Cl
p-Br
p-NO2
m-NO2
H
1
1
1
1.5
1
3g
3h
3i
p-Cl
3j
p-Br
p-NO2
m-NO2
1
aMaximum absorption wavelength in CH2Cl2 solution;
bMaximum emission wavelength in CH2Cl2 solution;
cMaximum emission wavelength in the solid state.
1
3j
1

JOURNAL OF CHEMICAL RESEARCH 2009 379
(Z)-2-(4-chlorophenyl)-3-(4-methoxyphenyl)acrylonitrile
(2j):
Experimental
M.p. 110–111°C (lit.,18 108.5–109°C); IR υmax(KBr)/cm-1: 3014,
2967, 2839, 2214, 1605, 1594, 1512, 1266, 1176, 1028; 1H NMR
(400 MHz, CDCl3) dH: 7.89 (d, J = 4.4 Hz, 2 H), 7.59 (d, J = 4.4 Hz,
2 H), 7.42 (dd, J = 4.8 Hz, J = 4.4 Hz, 3 H), 6.99 (d, J = 4.6 Hz, 2 H),
3.88 (s, 3 H).
Chemicals were purchased from Aldrich. Thin layer chromatography
(TLC) on commercial plates of silica gel GF254 was used to monitor
the progress of the reactions. Yields refer to isolated products after
purification. Melting points were determined on a YANACO melting
point apparatus and are uncorrected. Infrared(IR) spectra were taken
(Z)-3-(4-chlorophenyl)-2-phenylacrylonitrile(2k):M.p.109–110°C
on a Nicolet 230 FT-IR spectrophotometer. H NMR or 13C NMR
1
(lit.,18 110–110.5°C); IR υmax(KBr)/cm-1: 3047, 3009, 2218, 1601,
spectra were recorded in CDCl3 on Bruker Avance 500 DMX and
400 DMX spectrometers using TMS as internal standard. Elemental
analysis was carried out on an Eager 200 instrument. Mass spectra
were obtained from a Bruker Esquire 3000 plus instrument. Uv-vis
spectra were recorded on a Hitachi U-3300 spectrophotometer and
photoluminescence (PL) spectra were taken using a Hitachi F-4500
fluorescence spectrophotometer.
1
1516, 1019; H NMR (400 MHz, CDCl3) dH: 7.83 (d, J = 4.2 Hz,
2 H), 7.67 (d, J = 3.6 Hz, 2 H), 7.49–7.41 (m, 6 H).
(Z)-3-(4-chlorophenyl)-2-(3,4-dimethoxyphenyl)acrylonitrile (2l):
M.p. 115–116°C (lit.,5 115°C); IR υmax(KBr)/cm-1: 3057, 3030,
2218, 1588, 1492, 1091; 1H NMR (400 MHz, CDCl3)dH: 7.81 (d,
J = 4.4 Hz, 2 H), 7.43 (d, J = 4.6 Hz, 2 H), 7.38 (s, 1 H), 7.26 (t,
J = 2.2 Hz, J = 1.0 Hz, 1 H), 7.14 (d, J = 1.0 Hz, 1 H), 6.92 (d,
J = 4.2 Hz, 1 H), 3.96 (s, 3 H), 3.93 (s, 3H).
Typical procedure for synthesis of a, b-diarylacrylonitrile derivatives
Method 1: The arylacetonitrile (10 mmol) was added to one portion
of NaNH2 (22 mmol) in toluene (25 mL). The reaction mixture
was stirred for an appropriate time at room temperature or at reflux
temperature. Some toluene was added to dissolve the material and
this solution was then worked with H2O (30 mL) 3 times. After drying
over Na2SO4, filtration and removal of solvents the crude product was
purified by washing with small portions of cold acetone or by column
chromatography on silica gel using acetic ether/hexane as eluent.
Method 2: To a solution of the arylacetonitrile (10 mmol) and the
aromatic aldehyde (10 mmol) in EtOH (absolute, 20 mL) was added
in one portion 1 mmol NaOCH3. The reaction mixture was stirred for
an appropriate time at room temperature, filtered and washed with
small portions of cold EtOH to afford the products.
(Z)-2,3-bis(3,4-dimethoxyphenyl)acrylonitrile (2a): M.p. 154–
155°C (lit.,16 155–156°C); IR υmax (KBr)/cm-1: 3001, 2936, 2208,
1605, 1516, 1262, 1026; 1H NMR(400 MHz, CDCl3) dH: 7.68 (d,
J = 1.5 Hz, 1 H), 7.35 (d, J = 1.9 Hz, 2 H), 7.24–7.22 (m, 1 H), 7.13 (d,
J = 0.8 Hz, 1 H), 6.93–6.90 (m, 2 H), 3.97 (s, 3 H), 3.96 (s, 3 H), 3.95
(s, 3 H), 3.93 (s, 3 H). 13C NMR (CDCl3) d: 151.06 (C), 149.94 (C),
149.44 (C), 149.19 (C), 140.62 (CH), 127.86 (C), 127.08 (C), 124.18
(CH), 118.99 (CH), 118.97 (C), 111.47 (CH), 111.11 (CH), 110.88
(CH), 108.82 (CH), 108.74 (C), 56.24 (CH3), 56.23 (CH3), 56.19 (CH3),
56.17 (CH3). MS: m/z: Calcd for C19H19NO4 325.4. Found: 325.1.
(Z)-2,3-bis(4-methoxyphenyl)acrylonitrile (2b): M.p. 106–107°C
(lit.,5 108°C); IR υmax(KBr)/cm-1: 3002, 2963, 2838, 2213, 1605,
(Z)-3-(4-chlorophenyl)-2-(4-methoxyphenyl)acrylonitrile
(2m):
M.p. 109–110°C (lit.,18 108.5–109°C); IR υmax(KBr)/cm-1: 3010,
2938, 2832, 2219, 1605, 1511, 1095; 1H NMR (400 MHz, CDCl3) dH:
7.79 (d, J = 4.4 Hz, 2 H), 7.60 (d, J = 4.4 Hz, 2 H), 7.42 (d, J = 4.4 Hz,
2 H), 7.37 (s, 1 H), 6.96 (d, J = 4.4 Hz, 2 H), 3.86 (s, 3 H).
(Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile (2n): M.p. 176–177°C
(lit.,19 175–176°C); IR υmax(KBr)/cm-1: 3029, 2220, 1606, 1594,
1
1513, 1342, 1209, 1114; H NMR(400 MHz, CDCl3)dH: 8.34–8.32
(m, 2 H), 7.96–7.94 (m, 2 H), 7.88–7.86 (m, 2 H), 7.70 (s, 1 H), 7.52
(dd, J = 1.6 Hz, J = 1.4 Hz, 3H).
(Z)-3-(naphthalen-l-yl)-2-phenylacrylonitrile (3a): M.p. 108–
109°C (lit.,18 110–110.5°C); IR υmax(KBr)/cm-1: 3042, 2214, 1590,
1
1507, 1448, 778, 757, 678; H NMR(400 MHz, CDCl3)dH: 8.29(s,
1H), 8.10 (d, J = 7.2 Hz, 1H),7.97(m, 3H), 7.79 (d, J = 7.6 Hz, 2H),
7.59 (m, J = 8.0 Hz, 3H), 7.51 (m, 3H).
(Z)-2-(4-chlorophenyl)-3-(naphthalen-l-yl)acrylonitrile (3b): M.p.
173–174°C (lit.,18 174–175°C); IR υmax(KBr)/cm-1: 3042, 2218,
1594, 1490, 1407, 1095, 824, 778; 1H NMR (400 MHz, CDCl3)
dH: 8.27 (s, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.94 (m, 3H), 7.71 (d,
J = 8.8 Hz, 2H), 7.58 (m, 3H), 7.47 (d, J = 8.8 Hz, 2H).
(Z)-2-(4-bromophenyl)-3-(naphthalen-l-yl)acrylonitrile (3c): M.p.
179–180°C (lit.20); IR υmax(KBr)/cm-1: 3063, 2218, 1594, 1511,
1
1486, 1070, 824, 778; H NMR (400 MHz, CDCl3)dH: 8.28 (s,1H),
8.09 (d, J = 7.2 Hz, 1H), 7.94 (m, J = 8.0 Hz 3H), 7.60 (m, 7H).
(Z)-3-(naphthalen-l-yl)-2-(4-nitrophenyl)acrylonitrile (3d): M.p.
191–192°C (lit.21); IR υmax(KBr)/cm-1: 3071, 2214, 1594, 1569,
1
1514, 1254, 1176, 1024; H NMR (400 MHz, CDCl3) dH: 7.86 (d,
J = 4.2 Hz, 2 H), 7.59 (d, J = 4.4 Hz, 2 H), 7.36(s, 1 H), 6.97 (dd,
J = 3.6 Hz, J = 4.6 Hz, 4 H), 3.87 (d, J = 3.6 Hz, 6 H).
1
1515, 1344, 853, 778, 749; H NMR (400 MHz, CDCl3)dH: 8.50 (s,
1H), 8.36 (d, J = 8.8 Hz, 2H), 8.17 (d, J = 7.2 Hz, 1H) 7.95 (m, 5H),
7.61 (m, 3H).
(Z)-2,3-diphenylacrylonitrile (2c): M.p. 49–50°C (lit.17, 49–51°C);
IR υmax(KBr)/cm-1: 3055, 3032, 2219, 1492, 1447, 1020; H NMR
1
(Z)-3-(naphthalen-l-yl)-2-(3-nitrophenyl)acrylonitrile (3e): M.p.
(400 MHz, CDCl3) dH: 7.88 (d, J = 3.5 Hz, 2 H), 7.67 (d, J = 3.6 Hz,
2 H), 7.54 (s, 1 H), 7.49–7.38 (m, 6 H).
(Z)-2,3-bis(4-chlorophenyl)acrylonitrile (2d): M.p. 107–108°C
(lit.,17 108.5–109°C); IR υmax(KBr)/cm-1: 3043, 2226, 1593, 1495,
1095, 1016; 1H NMR (400 MHz, CDCl3) dH: 7.83(d, J = 4.4 Hz,
2 H), 7.61 (d, J = 4.4 Hz, 2 H), 7.46–7.42 (m, 5 H).
170–171°C; IR υmax(KBr)/cm-1: 3076, 2218, 1594, 1577, 1523,
1
1353, 774, 732; H NMR (400 MHz, CDCl3) dH: 8.64 (s, 1H), 8.45
(s, 1H), 8.31 (d, J = 8.0 Hz, 1H), 8.14(m, 2H), 7.99 (m, 3H), 7.71 (t,
J = 8.0 Hz, 1H),7.62 (m, 3H). Anal. Calcd for C19H12N2O2: C, 75.99;
H, 4.03; N, 9.33. Found: C, 75.72; H, 4.19; N, 9.22%.
(Z)-3-(naphthalene-2-yl)-2-phenylacrylonitrile (3f): M.p. 117–
118°C (lit.22); IR υmax(KBr)/cm-1: 3059, 2210, 1590, 1494, 1448,
820, 745, 683; 1H NMR(400 MHz, CDCl3) dH: 8.29 (s, 1H), 8.10 (d,
J = 8.8 Hz, 1H), 7.89 (m, J = 8.0 Hz, 2H), 7.73 (d, J = 7.2 Hz, 1H),
7.69 (s, 1H), 7.52 (s, 2H),7.54 (m, 2H), 7.46 (m, 3H).
(Z)-2-(3,4-dimethoxyphenyl)-3-phenylacrylonitrile (2e): M.p. 85–
86°C (lit.,5 87°C); IR υmax(KBr)/cm-1: 3002, 2954, 2834, 2222, 1601,
1
1512, 1265, 1252, 1148, 1024; H NMR(400 MHz, CDCl3) dH: 7.86
(dd, J = 0.8 Hz, J = 3.5 Hz, 2 H), 7.45 (dd, J = 3.7 Hz, J = 1.5 Hz, 4 H),
7.28–7.26 (m, 1 H), 7.15 (d, J = 1 Hz, 1 H), 6.92 (d, J = 4.2 Hz, 1 H),
3.96 (s, 3 H), 3.93 (s, 3 H).
(Z)-2-(4-chlorophenyl)-3-(naphthalen-2-yl)acrylonitrile
(3g):
M.p. 169–171°C; IR υmax(KBr)/cm-1: 3046, 2222, 1598, 1490, 1465,
1103, 828, 741; 1H NMR (400 MHz, CDCl3)dH: 8.27 (s, 1H), 8.08 (d,
J = 10.4 Hz, 1H), 7.88 (m, J = 8.4 Hz, 2H), 7.64 (t, J = 3.6 Hz, 1H),
7.57 (t, J = 7.2 Hz, 3H), 7.53 (d, J = 6.8 Hz, 2H), 7.43 (d, J = 8.4 Hz,
2H). Anal. Calcd for C19H12ClN: C, 78.76; H, 4.17; N, 4.83. Found:
C, 78.64; H, 4.30; N, 4.75%.
2-(4-chlorophenyl)-3-phenylacrylontrile (2f): M.p. 110–111°C
(lit.,18 110–110°C); IR υmax(KBr)/cm-1: 3056, 2218, 1598, 1495,
1095, 1013; 1H NMR (400 MHz, CDCl3)dH: 7.76 (d, J = 4.7 Hz,
2 H), 7.61 (d, J = 4.3 Hz, 2 H), 7.51 (s, 1 H), 7.48–7.41 (m, 5 H).
(Z)-2-(4-methoxyphenyl)-3-phenylacrylonitrile (2g): M.p. 92–
93°C (lit.5, 94°C); IR υmax(KBr)/cm-1: 3004, 2948, 2834, 2215, 1606,
1509, 1257, 1180, 1032; H NMR (400 MHz, CDCl3) dH: 7.87 (d,
J = 3.4 Hz, 2 H), 7.62 (d, J = 4.6 Hz, 2 H), 7.47–7.42 (m, 4 H), 6.97
(d, J = 4.4 Hz, 2 H), 3.86 (s, 3 H).
1
(Z)-2-(4-bromophenyl)-3-(naphthalen-2-yl)acrylonitrile (3h): M.p.
169–171°C; IR υmax(KBr)/cm-1: 3051, 2214, 1606, 1581, 1561, 1492,
1078, 824, 745; 1H NMR (400 MHz, CDCl3)dH: 8.29 (s, 1H), 8.09 (d,
J = 8.8 Hz, 1H), 7.92 (d, J = 8.0 Hz 2H), 7.87 (d, J = 7.6 Hz, 1H),7.67
(s, 1H), 7.59 (s, 6H). Anal. Calcd for C19H12BrN: C, 68.28; H, 3.62;
N, 4.19. Found: C, 68.26; H, 3.62; N, 4.19%.
(Z)-3-(naphthalen-2-yl)-2-(4-nitrophenyl)acrylonitrile (3i): M.p.
209–210°C (lit.21); IR υmax(KBr)/cm-1: 3055, 2210, 1606, 1586,
1511, 1340, 853, 745; 1H NMR (400 MHz, CDCl3)dH: 8.36 (t, J = 6.0
Hz, 3H),8.16 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 3.2 Hz, 2H), 7.91 (d,
J = 8.8 Hz, 3H), 7.85 (s, 1H), 7.60 (m, 2H).
(Z)-3-(4-methoxyphenyl)-2-phenylacrylonitrile(2h):M.p.91–92°C
(lit.,18 92.5–93.5°C); IR υmax(KBr)/cm-1: 3014, 2844, 2209,
1
1603, 1512, 1256, 1182; H NMR (400 MHz, CDCl3) dH: 7.90 (d,
J = 4.4 Hz, 2 H), 7.66 (d, J = 3.6 Hz, 2 H), 7.47–7.42 (m, 3 H), 7.38
(d, J = 3.8 Hz, 1 H), 6.99 (d, J = 4.6 Hz, 2 H), 3.88 (s, 3 H).
(Z)-2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile
(2i): M.p. 129–131°C (lit.,5 129°C); IR υmax(KBr)/cm-1: 3006, 2967,
1
2212, 1605, 1513, 1256, 1177, 1150; H NMR (400 MHz, CDCl3)
(Z)-3-(naphthalen-2-yl)-2-(3-nitrophenyl)acrylonitrile (3j): M.p.
209–210°C; IR υmax(KBr)/cm-1: 3076, 2218, 1594, 1577, 1523, 1353,
891, 774; 1H NMR (400 MHz, CDCl3)dH: 8.60 (s, 1H), 8.37 (s, 1H),
dH: 7.87 (d, J = 4.4 Hz, 2 H), 7.37 (s, 1 H), 7.23 (d, J = 4.2 Hz, 1 H),
7.13 (s, 1 H), 6.98 (d, J = 4.2 Hz, 2 H), 6.91 (d, J = 4.2 Hz, 1 H), 3.96
(s, 3 H), 3.93 (s, 3 H), 3.87 (s, 3 H).

380 JOURNAL OF CHEMICAL RESEARCH 2009
7
F. Fringuelli, G. Pani, O. Piermatti and F. Pizzo, Tetrahedron, 1994, 50,
11499-11508.
J.H. Russel and H. Hunziker, Tetrahedron Lett., 1969, 4035-4037.
K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani and
K. Kaneda, J. Am. Chem. Soc., 2004, 126, 5662-5663.
8.29 (d, J = 8.0 Hz, 1H), 8.15 (t, J = 7.6 Hz, 1H),8.08 (d, J = 8.0 Hz,
1H), 7.97 (d, J = 8.8 Hz, 2H), 7.91 (d, J = 8.0 Hz, 1H) 7.84 (s, 1H),
7.70 (t, J = 8.0 Hz, 1H), 7.60 (m, 2H). Anal. Calcd for C19H12N2O2:
C, 75.99; H, 4.03; N, 9.33. Found: C, 75.87; H, 4.15; N, 9.26%.
8
9
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11 M.X. Yu, J.P. Duan, C.H. Lin, C.H. Cheng and Y.T. Tao, Chem. Mater.,
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We thank the Key Industrial Catalysis Subject of Zhejiang
Province, P. R. China for financial support.
12 M.X. Yu, M.J. Wang, X.H. Chen, B.B. Hong, X.Y. Zhang and C.H. Cheng,
J. Chem. Res., 2005, 9, 558-560.
13 M.X. Yu, X.H. Chen and C.H. Cheng, Chin. J. Org. Chem., 2005, 25,
218-221.
Received 17 January 2009; accepted 26 March 2009
Paper 09/0398 doi: 10.3184/030823409X460687
Published online: 30 June 2009
14 M.X. Yu, W.J. Wen and C.H. Cheng, Chin. J. Org. Chem., 2006, 26,
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