A facile synthesis of 1,4-bis-(3-Aryl-3-oxo-1-propenyl)benzenes under microwave irradiation

Article abstract of DOI:10.1081/SCC-120014048

1,4-bis(3-Aryl-3-oxo-1-propenyl)benzenes were synthesized by 1,4-benzenedicarboxaldehyde with substituted acetophenones in the presence of sodium hydroxide under microwave irradiation with good yields.

Full text of DOI:10.1081/SCC-120014048

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A FACILE SYNTHESIS OF 1,4-BIS- (3-ARYL-3-OXO-1-
PROPENYL)BENZENES UNDER MICROWAVE IRRADIATION
Jian-Feng Zhou a , Jun-Feng Zhou b , Zheng-Cai Zou b & Jun-Cai Feng c
a Department of Chemistry , Huaiyin Normal College , Huaian, 223001, P.R. China
b Department of Chemistry , Nanjing University , Nanjing, 210093, P.R. China
c Department of Chemistry , Nanjing University , Nanjing, 210093, P.R. China
Published online: 16 Aug 2006.
To cite this article: Jian-Feng Zhou , Jun-Feng Zhou , Zheng-Cai Zou & Jun-Cai Feng (2002) A FACILE SYNTHESIS OF 1,4-BIS-
(3-ARYL-3-OXO-1-PROPENYL)BENZENES UNDER MICROWAVE IRRADIATION, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 32:21, 3389-3392, DOI: 10.1081/SCC-120014048
To link to this article: http://dx.doi.org/10.1081/SCC-120014048
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SYNTHETIC COMMUNICATIONS
Vol. 32, No. 21, pp. 3389–3392, 2002
A FACILE SYNTHESIS OF 1,4-BIS-
(3-ARYL-3-OXO-1-PROPENYL)BENZENES
UNDER MICROWAVE IRRADIATION
*
Jian-Feng Zhou, Jun-Feng Zhou, Zheng-Cai Zou,
and Jun-Cai Fengy
Department of Chemistry, Nanjing University,
210093 Nanjing, P.R. China
ABSTRACT
1,4-bis(3-Aryl-3-oxo-1-propenyl)benzenes were synthesized by
1,4-benzenedicarboxaldehyde with substituted acetophenones
in the presence of sodium hydroxide under microwave
irradiation with good yields.
1,4-bis(3-Aryl-3-oxo-1-propenyl)benzenes are important intermediates
in organic synthesis,[1,2] which are usually obtained by the condensation of
1,4-benzenedicarboxaldehyde and substituted acetophenones in the presence
of potassium hydroxide solution.[3,4] Also, we had previously reported that
synthesis of 1,4-bis(3-aryl-3-oxo-1-propenyl)benzenes from 1,4-benzene-
dicarboxaldehyde and substituted acetophenones using bis(4-methox-
phenyl)telluroxide (BMPTO) as catalyst in DMSO.[5] However, the
*Current address: Department of Chemistry, Huaiyin Normal College, Huaian
223001, P.R. China.
yCorresponding author. E-mail: jcfeng@nju.edu.cn
3389
DOI: 10.1081/SCC-120014048
Copyright & 2002 by Marcel Dekker, Inc.
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3390
ZHOU ET AL.
substituted acetophenones were easily self-condensed in base solution and
the BMPTO was not readily available in the above synthetic methods.
The recent years, the wide applicability of microwave irradiation in
chemical reaction enhancement is due to high reaction rate with formation
of cleaner products and the operation simplicity.[6–8] We found that the
reaction between 1,4-benzenedicarboxaldehyde and substituted aceto-
phenones using sodium hydroxide as catalyst in ethanol under microwave
irradiation was easy and the reaction was finished in short time with good
yields. Here, we would like to report a facile synthesis of 1,4-bis(3-aryl-
3-oxo-1-propenyl)benzenes from 1,4-benzenedicarboxaldehyde and substi-
tuted acetophenones in the presence of a catalytic quantity of sodium
hydroxide in ethanol under microwave irradiation, 3d, 3e, 3f and 3g were
not accumulated in literature. The reactions were generally finished in
2–4 min with 66–86% yields and easy work-up.
The synthetic route is shown as following:
The results obtained are shown in Table 1.
Table 1. Reaction Times and Yields of Products 3a–g Under
Microwave Irradiation
Reaction Time
(min)
Yielda
(%)
Products
Ar
3a
3b
3c
3d
3e
3f
C6H5
4-ClC6H4
4-CH3OC6H4
3-BrC6H4
4-CH3C6H4
3,4-(CH3)2C6H3
2-Naphthyl
4
2
2
2
3
3
2
81
79
80
66
81
85
68
3g
aYields of the isolated products.

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1,4-BIS(3-ARYL-3-OXO-1-PROPENYL)BENZENES
3391
EXPERIMENTAL
Melting points were determined in open capillaries and uncorrected.
1
IR spectra were recorded on a Nicolet FT-IR 5DX instrument. H NMR
were measured on a Bruker DPX 300 MHz spectrometer or Bruker QC-P
200 MHz spectrometer in DMSO with TMS as internal standard. Elemental
analyses were carried on a Perkin-Elmer 240C elemental analyzer. The reac-
tions were carried out with a modified commercial microwave oven (Sanle
WP650D 650 W) under atmospheric pressure.
General Procedure for the Synthesis of 3a–g
Into an Erlenmeyer flask (25 mL) equipped with reflux condenser were
introduced the 1,4-benzenedicarboxaldehyde 1 (1 mmol), substituted aceto-
phenone 2 (2 mmol), a catalytic quantity of powder sodium hydroxide
(10 mol%), dry ethanol (3 mL). After irradiation for 2–4 min (monitored by
TLC) at 130 W (i.e., 20% microwave power). The mixture were cooled and
then filtered, washed with cooled ethanol followed by water till the washings
were neutral. The crude product was recrystallized from ethanol to give a
pure sample. Specific details on each product are as follows:
3a: M.p. 192–193ꢀC (194–195ꢀC).[5] 1H NMR (DMSO-d6) ꢀ: 7.79
(2H, d, J ¼ 15.6 Hz), 8.06 (2H, d, J ¼ 15.6 Hz), 8.00–7.75 (10H, m),
8.20–8.17 (4H, m). IR (KBr): 1658, 979 cmꢁ1
.
3b: M.p. 252–253ꢀC (253–254ꢀC).[5] 1H NMR (DMSO-d6) ꢀ: 7.37
(2H, d, J ¼ 15.6 Hz), 7.75 (4H, d, J ¼ 9.0 Hz), 7.98 (4H, d, J ¼ 9.0 Hz),
8.25 (2H, d, J ¼ 15.6 Hz). IR (KBr): 1658, 974 cmꢁ1
.
3c: M.p. 241–242ꢀC (243–244ꢀC).[5] 1H NMR (DMSO-d6) ꢀ: 3.91
(6H, s), 7.03 (4H, d, J ¼ 9.0 Hz), 7.31 (4H, d, J ¼ 12.4 Hz), 7.76 (4H, m),
8.09 (2H, d, J ¼ 12.4 Hz), 8.30 (4H, d, J ¼ 9.0 Hz). IR (KBr): 1660, 971 cmꢁ1
.
3d: M.p. 204–206ꢀC. H NMR (DMSO-d6) ꢀ: 7.79–7.54 (4H, m), 7.82
(2H, d, J ¼ 15.6 Hz), 8.17–8.03 (6H, m), 8.25 (2H, d, J ¼ 15.6 Hz), 8.35
(2H, s). IR (KBr): 1661, 971 cmꢁ1. Anal. calcd. (%) for C24H16Br2O2: C,
57.95; H, 3.22. Found: C, 57.72; H, 3.09.
1
3e: M.p. 220–222ꢀC. H NMR (DMSO-d6) ꢀ: 2.42 (6H, s), 7.41–7.39
1
(4H, d), 7.76 (2H, d, J ¼ 15.6 Hz), 8.04 (2H, d, J ¼ 15.6 Hz), 8.12–7.99
(8H, m). IR (KBr): 1655, 984 cmꢁ1. Anal. calcd. (%) for C26H22O2:
C, 85.25; H, 6.01. Found: C, 84.99; H, 6.04.
3f: M.p. 214–216ꢀC. 1H NMR (DMSO-d6) ꢀ: 2.33 (6H, s), 2.35 (6H, s),
7.76 (2H, d, J ¼ 15.6 Hz), 7.99–7.34 (10H, m), 8.03 (2H, d, J ¼ 15.6 Hz). IR
(KBr): 1657, 980 cmꢁ1. Anal. calcd. (%) for C28H26O2: C, 85.28; H, 6.60.
Found: C, 85.01; H, 6.53.

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3392
ZHOU ET AL.
3g: M.p. 232–234ꢀC. 1H NMR (DMSO-d6) ꢀ: 7.65–8.10 (14H, m), 7.88
(2H, d, J ¼ 15.6 Hz), 8.16–8.21 (4H, m), 8.26 (2H, d, J ¼ 15.6 Hz). IR (KBr):
1659, 979 cmꢁ1. Anal. calcd. (%) for C32H22O2: C, 87.67; H, 5.02. Found:
C, 87.46; H, 5.04.
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Received in Japan July 10, 2001