An efficient microwave assisted eco-friendly synthesis of 6-chloro-3-(3-arylacryloyl)-2-methyl-4-phenylquinolines and their conversion to 6-chloro-3-(1-phenyl-5-aryl-4,5-dihydro-1h-pyrazol-3-yl)-2-methyl-4- phenylquinolines

Article abstract of DOI:10.1002/jccs.201100162

An eco-friendly basic alumina catalyzed protocol for the synthesis of some new quinolinyl chalcones has been developed by microwave assisted methods which in turn are converted to pyrazoline derivatives.

Full text of DOI:10.1002/jccs.201100162

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Article
An Efficient Microwave Assisted Eco-friendly Synthesis of
6-Chloro-3-(3-arylacryloyl)-2-methyl-4-phenylquinolines and their Conversion to
6-Chloro-3-(1-phenyl-5-aryl-4,5-dihydro-1H-pyrazol- 3-yl)-2-methyl-4-phenylquinolines
S. Sarveswari and V. Vijayakumar
Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore-632014, Tamil Nadu, India
(Received March 21, 2011; Accepted July 14, 2011; Published Online July 27, 2011; DOI: 10.1002/jccs.201100162)
An eco-friendly basic alumina catalyzed protocol for the synthesis of some new quinolinyl chalcones has
been developed by microwave assisted methods which in turn are converted to pyrazoline derivatives.
Keywords: Microwave assisted synthesis; Chalcones; Reusable alumina catalyst; Pyrazolines.
INTRODUCTION
The most common and widespread compounds of
are unique in the flavonoid family13 for example kava ex-
tracts are used for bladder cancer prevention that has
kavalactones and flavokawains (chalcones) as the major
constituents. Hydroxychalcone derivatives are also re-
ported to have cytotoxic, anti-HIV properties.14,15 Heme
oxygenase activity16 has been significantly increased by
2-hydroxychalcone, 2,2¢-hydroxychalcone and 2,2¢,4¢-tri-
hydroxy chalcone. The xanthohumol is a potent inhibitor of
apo-b-secretion for the prevention of atherosclerosis.17
Hence there is a continuing interest in efficient synthesis of
quinolines and chalcones to get the derivatives with im-
proved activities.18,19 In continuation of our interest in the
synthesis of quinolinyl chalcones,20 Herein we report the
eco-friendly synthesis of chalcones and their conversion to
biologically important pyrazolines. Mamolo et al., have
synthesized21 a series of 5-aryl-1-isonicotinoyl-3-(pyridin-
2-yl)-4,5-dihydro-1H-pyrazoles in a three-step process, in
low yields, which involved an aldol condensation, cyclo-
condensation with hydrazine and N-acylation with isonico-
tinoyl chloride. Powers et al., reported22 the synthesis pyr-
azoline through the reaction of chalcones on phenyl hy-
drazine hydrochloride in presence of sodium hydroxide in
absolute ethanol at 70 °C, but it requires longer reaction
time (8 h). Levai et al., synthesized23 3,5-diaryl-2-pyrazo-
lines through the reaction of chloro chalcones on phenyl
hydrazine in acetic acid under refluxing conditions for 3 h.,
by keeping the ratio of chlorochalcones and phenyl hy-
drazine 1:5 ratio, but these reaction conditions suffer eco-
nomic and environmental concerns. Carter et al., reported24
the synthesis of pyrazoline esters as an intermediate in the
process a,b-diamino acids. Sahu et al., reported25 the syn-
chalconoid group are the chalcones, which possess a 1,3-
diaryl-2-propen-1-one carbon framework. The importance
of these compounds is due not only to their colours but also
to their chemical in addition to biological activities and the
fact that they are good accessible starting materials for con-
struction of various heterocyclic derivatives.1 They are nat-
urally occurring plant metabolites can be regarded as
open-chain flavonoids possess a broad spectrum of biolog-
ical activities, including antimalarial, antituberculosis, an-
tibacterial, anthelmintic, amoebicidal, antiulcer, antimi-
crobial, antiprotozoal, cytotoxic, immuno suppressive ac-
tivities,1-4 antiviral, insecticidal, antioxidant, antiinflam-
matory and several anticancer activities such as inhibitors
of cancer cellproliferation, carcinogenesis and metasta-
sis.5-8 Natural and synthetic chalcones have shown strong
anti proliferative effects in both primary and established
ovarian cancer cells9 and in gastric cancer HGC-27 cells.10
Because of a,b-unsaturated ketones in their structures,
chalcones have a preferential reactivity towards thiols in
contrast to amino and hydroxyl groups. Therefore, chal-
cones are less likely to interact with nucleic acids and
hence avoid the problems of mutagenicity and carcinoge-
nicity associated with certain alkylating agents in cancer
chemotherapy.11 In addition, chalcones are susceptible to
the Michael addition at enone (CH=CHCO), which can
cause binding to particular receptors and lead to the induc-
tion of phase II enzymes against carcinogens.12
Chalcones are the intermediate precursors for all
flavonoids in the phenyl propanoid pathway in plants and
* Corresponding author. Tel: 04162202332; E-mail: sarveswari@gmail.com
66
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Microwave Assisted Synthesis of Quinolinyl Chalcones
thesis of few pyrazoline derivatives with p-nitro and p-hy-
droxy group in aryl moiety of pyrazoline analogs. Sayed
Amr et al., synthesized26 the fused pyrazolines with ster-
oidal moieties and evaluated them as 5a-reductase inhibi-
tors, which are found to be comparable to standard drug
anastrozole. Hence based on the above literature here in we
report the synthesis some new pyrazoline derivatives.
Synthesis of E-(6-chloro-3-(3-arylacrylo-
yl)-2-methyl-4-phenylquinolines
Scheme I
RESULTS AND DISCUSSION
yl), 1573 cm-1 (conjugated alkene function). The proton
NMR spectrum of 3e displayed two doublets at d 6.28 ppm,
d 7.15 ppm with characteristic coupling constant of (J) 15.6
Hz, which confirms the formation of chalcones (a,b-unsat-
urated ketone). This higher coupling constant value indi-
cates, the a,b-unsaturated protons are trans to each other, it
also confirmed by single crytal structure of some of similar
derivatives. In a similar way, proton chemical shift values
of other members in the series are assigned. The com-
pounds 3f, 3h, 3l were recrystallized using ethanol and the
obtained single crystals subjected to the X-ray diffraction
studies and reported.27 The compounds (3a-d) in turn are
converted into pyrazoline derivatives (4a-d)28 (Scheme II).
In the present work compound 1 has been converted
into its corresponding chalcones namely 6-chloro-3-(3-
arylacryloyl)-2-methyl-4-phenylquinolines (3a-j) (Scheme
I) by stirring the mixture of compound 1 and arylaldehydes
in presence of potassium hydroxide in ethanol for 12 h. The
completion of the reaction has been monitored by TLC. Af-
ter completion of the reaction, the reaction mixture was
concentrated, poured onto cold water and acidified with
acetic acid. The crude product was purified by column
chromatography using 8:2 mixture of petroleum ether-
ethylacetate. Equimolar mixture of 1 and various arylalde-
hydes adsorbed on basic alumina was irradiated under the
microwave for 2-4 minutes with the power level of 240 W
to afford the product 3a-j. After completion of the reaction,
the product was recovered by washing with CHCl3 and the
washings were distilled to reuse the chloroform using ro-
tary evaporator. This protocol eliminates useage of excess
of alkali and the subsequent neutralisation procedures. The
crude product was purified by column chromatography us-
ing 8:2 mixture of petroleum ether ethylacetate. The same
reaction could be achieved without alumina catalyst with
excess of KOH base, the product recovery in this involves
neutralization with acetic acid, after evaporation the resi-
due washed with petroleum ether and purified by column
chromatography using 8:2 mixture of petroleum ether-eth-
ylacetate. The reaction involved in synthesis of chalcones
is Aldol condensation, is normally carried out in presence
of bases and acidic work up to avoid the usage of bases, we
tried the same reaction with basic alumina catalyst it results
in the same chalcone formation. All the synthesized 6-chlo-
ro-3-(3-arylacryloyl)-2-methyl-4-phenylquinolines (3a-j)
have been characterized by IR, 1H NMR spectral data. The
compound 3e has been taken as representative example and
its spectral characterization has been described below. The
IR spectrum of 3e shows the following characteristic ab-
sorption frequencies: 1657 cm-1 (a,b-unsaturated carbon-
Synthesis 6-chloro-3-(aryl)-4,5-dihydro-
1H-pyrazol-3-yl)-2-methyl-4-phenylquin
olines
Scheme II
1
Three doublet of doublets in aliphatic region of H
NMR spectrum of pyrazoline derivatives (4a-d) at d 2.23
ppm (1H, dd, JAM = 17.7 Hz and JAX = 5.5 Hz), d 3.26 ppm
(1H, dd, JAM = 17.7 Hz and JMX = 12.3 Hz), d 5.34 ppm (1H,
dd, JMX = 12.3 Hz and JAX = 5.5 Hz) confirms the formation
of pyrazoline ring. According to Ozdemir et al., hydro-
zones may formed28 as intermediate and subsequent addi-
tion of -NH on olefinic bond of propenone moiety led to the
product. Condensation of chalcones with phenyl hydra-
zine. The formation of 4a-d instead of its regioisomer is fa-
vored via hydrazone formation.30 Under these reaction
conditions, the product stereochemistry may be determined
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67

Article
Sarveswari and Vijayakumar
by the stereoselective enamine-imine tautomerism take
place giving rise to the preferred direction of the proton on
C-4 trans to the phenyl group at C-5 (Fig. 1). While 3-pyr-
azoline isomerizes to the more stable 2-pyrazoline.31
The proton chemical shift values of other members of
this series are assigned and given in experimental section.
The yield time, and power level are given in Table 1. When
the reaction durations were compared among microwave
assisted synthesis and the conventional method for the syn-
thesis of chalcones, present method requires much lesser
duration with almost equal yield as in the conventional
method. Hence the microwave assisted synthesis can be re-
garded as an efficient method for the synthesis of these
compounds.
Table 1. Physical data of compound (3a-j, 4a-d)
Time
[in min]
S. NO
Ar
Yielda Yieldb
3a
2-methoxy-8-
3
74
68
methylquinolin-3-yl
2-naphthyl
4-fluorophenyl
Thiophen-2-yl
Benzo[d][1,3]dioxo-6-yl
4-ethoxyphenyl
3,4-dimethoxy phenyl
2-methoxyphenyl
3-methoxyphenyl
4-chlorophenyl
2-methoxy-8-
3b
3c
3d
3e
3f
3
4
3
3
3
4
4
4
4
7
78
82
80
85
73
85
70
77
74
74
74
75
78
83
67
83
68
63
69
61
3g
3h
3i
3j
4a
methylquinolin-3-yl
2-naphthyl
4-fluorophenyl
Thiophen-2-yl
4b
4c
4d
10
10
10
65
78
80
62
76
75
EXPERIMENTAL
Solvents and reagents were commercially sourced
and used without further purification, which Melting
points were taken on Elchem Microprocessor based DT ap-
paratus in open capillary tubes and are corrected with ben-
zoic acid. IR spectra were obtained on an Avatar-330 FTIR
spectrophotometer (Thermo Nicolet) using KBr pellets,
and only noteworthy absorption levels (reciprocal centime-
ters) are listed. The NMR spectra were recorded on a
Bruker – 400 MHz spectrometer using TMS as internal
standard (chemical shifts d in ppm). Mass spectra were re-
corded on LCMS by Agilent 1200 series LC and Micro-
mass zQ spectrometer. Microwave oven used is of syn-
thetic microwave: CATAR with maximum power of 700W.
Thin-layered chromatography (TLC) was performed on
plates coated with TLC silica gel (s.d. fine). Visualization
was made with iodine chamber. Column chromatography
was performed by using silica gel (60-120 mesh). Elemen-
tal analysis was done in SAIF-CDRI-Luckow.
a Yield of microwave assisted synthesis at 240W.
b Yield by conventional method.
was dissolved in 3-4 mL chloroform-methanol (1:2) and
adsorbed on 1 gm of basic alumina evaporated to dryness in
ethanol was irradiated for 3-4 min. at 240 W. The dry solid
obtained was cooled and extracted with little amount of
chloroform, then the solution was distilled to afford the
product as a solid. The crude product was purified by col-
umn chromatography using 8:2 mixture of petroleum ether
ethylacetate.
(b) Conventional method
A mixture of 6-chloro-2-methyl-4-phenylquinoline-
3-yl-ethanone (2.95 g, 0.01 mol), aryl aldehydes (0.01 mol)
and 0.5 gm of KOH in ethanol was stirred 12 h at room tem-
perature (The reaction was monitored by thin layer chro-
matography). The reaction mixture was concentrated and
poured on to water and acidified with acetic acid to afford
the product as a solid. The crude product was purified by
column chromatography using 8:2 mixture of petroleum
ether ethylacetate.
General procedure for the synthesis of E-(6-chloro-3-
(3-arylacryloyl)-2-methyl-4-phenylquinolines) (3a-j)
(a) By microwave assisted method
A mixture of 6-chloro-2-methyl-4-phenylquinoline-
3-yl-ethanone (2.95 g, 0.01 mol), aryl aldehyde (0.01 mol)
Synthesis of 6-Chloro-3-(1-phenyl-5-(3-methoxy-8-
methylquinolin-4-yl)-4,5-dihydro-1H-pyrazol-3-yl)-2-
methyl-4-phenylquinoline (4a)
(a) By conventional method
A mixture of corresponding 6-chloro-3-(3-(2-meth-
oxy-8-methylquinolin-3-yl)acryloyl)-4-phenyl-2-methyl
quinoline (3a) (0.5 g, 0.001 M) and phenyl hydrazine (0.76
Fig. 1. Mechanism of formation of pyrazolines.
68
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Microwave Assisted Synthesis of Quinolinyl Chalcones
g, 0.007 M) in distilled methanol was refluxed for about 8
h, the resulting mixture concentrated to remove methanol,
then poured on to ice and neutralized with dil. HCl. The re-
sultant solid was filtered, dried and purified by column
chromatography using 1:1 mixture of chloroform and pe-
troleum ether. The compound was recrystallized from
methanol. The reproducibility of the synthetic procedure
was checked with other acryloylquinolines (3b-d) to get
the corresponding pyrazoline derivatives (4b-d).
(b) By microwave assisted method
7.22 (d, 1H, J = 7.3 Hz), 7.29 (d, 1H, J = 7.3 Hz), 7.38-7.45
(m, 5H), 7.39 (d, 1H, J = 2.4 Hz), 7.84 (dd, 1H, J = 9.0 Hz,
2.4 Hz), 8.11 (d, 1H, J = 9.0 Hz); GCMS: m/z 401.1 [M+].
(3d) Very pale yellow solid; Mp: 210-212 °C; IR
(KBr): 1657 (C=O), 1571 (C=C) cm-1; 1H NMR (400 MHz,
CDCl3): d 2.63 (s, 3H), 6.28 (d, 1H, J = 15.6 Hz), 7.06 (d,
1H, J = 3.6 Hz), 7.15 (d, 1H, J = 15.6 Hz), 7.22 (t, 1H, J =
4.0 Hz), 7.32-7.36 (m, 5H), 7.34 (d, 1H, J = 3.2 Hz), 7.51
(d, 1H, J = 2.0 Hz), 7.62 (dd, 1H, J = 8.8 Hz, 2.4 Hz), 7.99
(d, 1H, J = 9.2 Hz), ms: m/z: 389.06.
A mixture of corresponding 6-chloro-3-(3-(2-meth-
oxy-8-methylquinolin-3-yl)acryloyl)-4-phenyl-2-methyl
quinoline (3a) (0.5 g, 0.001 M) and phenyl hydrazine (0.76
g, 0.007 M) in distilled methanol was irradiated for 7-10
min. at 240 W, the resulting mixture concentrated to re-
move methanol, then poured on to ice and neutralized with
dil. HCl. The resultant solid was filtered, dried and purified
by column chromatography using 1:1 mixture of chloro-
form and petroleum ether. The reproducibility of the syn-
thetic procedure was checked with other acryloylquino-
lines (3b-d) to get the corresponding pyrazoline deriva-
tives (4b-d).
(3e) Pale yellow solid; Mp: 152-53 °C; IR (KBr):
1
1634 (C=O), 1551 cm-1 (C=C); H NMR (400 MHz,
CDCl3): d 2.57 ppm (s, 3H), 6.06 (s, 2H), 6.70 (d, 1H, J =
16.2 Hz), 6.89 (d, 1H, J = 8.1 Hz), 7.13 (dd, 1H, J = 8.1 Hz,
1.5 Hz), 7.21 (d, 1H, J = 16.2 Hz), 7.28 (d, 1H, J = 1.6 Hz),
7.35-7.36 (m, 2H), 7.39 (d, 1H, J = 2.4 Hz), 7.43-7.45 (m,
3H), 7.84 (dd, 1H, J = 9.0 Hz, 2.4 Hz), 8.11 (d, 1H, J = 9.0
Hz); GCMS: m/z: 428.1[M+1]+.
(3f) Yellow solid; Mp: 152-153 °C; IR (KBr): 1639
(C=O), 1599 cm-1 (C=C); 1H NMR (400 MHz, CDCl3): d
1.3 (t, 3H), 2.58 (s, 3H), 4.05 ppm (q, 2H). 6.69 (d, 1H, J =
16.2 Hz), 6.90 (d, 2H, J = 8.8 Hz), 7.24 (d, 1H, J = 16.2
Hz), 7.34-7.36 (m, 3H), 7.39 (d, 1H, J = 2.2), 7.42-7.46 (m,
2H), 7.57 (d, 2H, J = 8.8 Hz), 7.85 (dd, 1H, J = 9.0, 2.2),
8.12 (d, 1H, J = 9.0 Hz), ESMS: m/z 427 [M+].
The compound was recrystallized from methanol.
Structural assignments of the products were made on the
basis of spectral data.
(3a) Pale yellow solid; Mp: 240-241 °C; IR (KBr):
(3g) Yellow solid; Mp: 181-182 °C; IR (KBr): 1641
(C=O), 1597 cm-1 (C=C); 1H NMR (400 MHz, CDCl3): d
2.58 (s, 3H), 3.74 (s, 3H), 3.77 (s, 3H), 6.77 (d, 1H, J = 15.8
Hz), 6.93 (d, 1H, J = 8.8 Hz), 7.18 (d, 1H, J = 2.0 Hz), 7.22
(d, 1H, J = 15.8 Hz), 7.37-7.35 (m, 3H), 7.40 (d, 1H, J = 2.2
Hz), 7.47-7.43 (m, 3H), 7.86 (dd, 1H, J = 9.0 Hz, 2.2 Hz),
8.12 (d, 1H, J = 8.8 Hz). ESMS: m/z 443 [M+].
1
1656 (C=O), 1565 cm-1 (C=C); H NMR (400 MHz,
CDCl3): d 2.72 ppm (s, 3H), 2.88 (s, 3H), 4.06 (s, 3H),
6.77-6.95 (m, 3H), 7.05 (d, 1H, J = 16.0 Hz), 7.15 (d, 1H, J
= 5.1 Hz), 7.39 (d, 2H, J = 7.8 Hz), 7.43 (d, 1H, J = 16.0
Hz), 7.48 (s, 1H), 7.57 (t, 1H, J = 7.5 Hz), 7.72 (d, 1H, J =
7.3 Hz), 7.82 (d, 1H, J = 8.1 Hz), 7.84 (dd, 1H, J = 9.0 Hz,
2.4 Hz), 8.14 (d, 1H, J = 9.0 Hz); ESMS: m/z 478 [M+];
Anal. Calcd. for C30H23ClN2O2: C, 75.23; H, 4.84; N, 5.85.
Found: C, 74.83; H, 5.04; N, 5.58.
(3h) Pale yellow solid; Mp: 150-53 °C; IR (KBr):
1
1554 (C=C), 1637 cm-1 (C=O); H NMR (400 MHz,
CDCl3): d 2.58 (s, 3H), 3.78 ppm (s, 3H, -OCH3), 6.68 (d,
1H, J = 16.5 Hz), 6.88 (d, 1H, J = 16.5 Hz), 7.31 (d, 1H, J =
2.7 Hz), 7.69-7.58 (m, 9H), 7.70 (dd, 1H, J = 8.9 Hz, 2.3
Hz), 8.08 (d, 1H, J = 8.9 Hz); Es ms: m/z 413 [M+].
(3i) Pale yellow solid; Mp: 124-126 °C; IR (KBr):
(3b) Yellow solid; Mp: 162-164 °C; IR (KBr): 1556
(C=C), 1689 cm-1 (C=O); 1H NMR (400 MHz, CDCl3): d
2.58 (s, 3H), 2.61 (s, 3H), 6.94 (d, 1H, J = 16.6 Hz), 7.50 (d,
1H, J = 16.6 Hz), 7.53-7.55 (m, 1H), 7.57-7.51 (m, 6H),
7.76 (dd, 1H, J = 9.6 Hz, 1.6 Hz), 7.92-7.84 (m, 5H), 8.14
ppm (m, 2H); GCMS: m/z 433.2 [M+].
1
1636 (C=O), 1552 cm-1 (C=C); H NMR (400 MHz,
CDCl3): d (ppm) 2.71 (s, 3H), 3.78 (-OCH3), 6.58 (d, 1H,
16.2 Hz), 6.83 (d, 1H, J = 1.7 Hz), 6.92 (dd, 2H, J = 8.7 Hz,
2.4 Hz), 7.06 (d, 1H, J = 16.2 Hz), 7.31-7.22 (m, 3H) 7.44-
7.39 (m, 3H), 7.59 (d, 1H, J = 2.2 Hz), 7.69 (dd, 1H, J = 8.9
Hz, 2.4 Hz), 8.09 (d, 1H, J = 8.9 Hz); GCMS: m/z 414
(3c) Yellow solid; Mp: 145-147 °C; IR (KBr): 1556
(C=C), 1699 cm-1 (C=O); 1H NMR (400 MHz, CDCl3): d
2.58 ppm (s, 3H), 6.70 (t, 1H, J = 6.2 Hz), 6.79 (d, 1H, J =
15.0 Hz), 6.92 (t, 1H, J = 8.9 Hz), 7.20 (d, 1H, J = 15.0 Hz),
J. Chin. Chem. Soc. 2012, 59, 66-71
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69

Article
Sarveswari and Vijayakumar
[M+1], 413 [M+].
pounds; Wiley: New York, 1981; p 201.
2. Grayer, R. J. In Methods in Plant Biochemistry; Dey, P. M.;
Harborne, J. B.; Eds.; Academic Press: London, 1989; pp
283-323.
(3j) Pale yellow solid; Mp: 184-186 °C; IR (KBr):
1
1649 (C=O), 1555 cm-1 (C=C); H NMR (400 MHz,
CDCl3): d 3.32 ppm (s, 3H), 6.88 (d, 1H, J = 16.2 Hz),
7.30-7.34 (m, 2H), 7.38 (d, 1H, J = 16.2 Hz), 7.41-7.51 (m,
7H), 7.83 (d, 1H, J = 2.4 Hz), 7.85 (dd, 1H, J = 9.0, 2.4 Hz),
8.10 (d, 1H, J = 9.0 Hz); GCMS: m/z 417 [M] +.
3. Fabiane, L.; Guzela, M.; Rodrigues, A. T.; Iriane Eger-
Mangrich, R. C.; Steindel, M.; Grisard, E. C.; Assreuy, J.;
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ther. 2003, 4, 1449.
(4a) Deep yellow solid (with greenish yellow flo-
rescence in CHCl3); Mp 183-85 °C; IR (KBr): 1629 (C=N),
4. Dimmock, J. R.; Elias, D. W.; Beazely, M. A; Kandepu, N.
M. Curr. Med. Chem. 1999, 6, 1125.
1
1492 (C=C), 2923 (CH aliphatic) cm-1; H NMR (400
5. Baba, M.; Asano, R.; Takigami, I. Biol. Pharm. Bull. 2002,
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MHz, CDCl3): d 2.23 (dd, 1H, J = 17.7 Hz, 5.5 Hz), 2.72 (s,
3H), 2.88 (s, 3H), 3.26 (dd, 1H, J = 17.7 Hz, 12.3 Hz), 4.06
ppm (s, 3H), 5.34 (dd, 1H, J = 12.3 Hz, 5.5 Hz), 6.77-6.95
(m, 5H), 7.17-7.30 (m, 5H), 7.18 (d, 1H, J = 5.1 Hz),
7.43-7.49 (m, 4H), 7.62 (d, 1H, J = 9.3 Hz), 8.06 (d, 1H, J =
8.7 Hz), ms: m/z 568.2 (M+).
6. Yamazaki, S.; Morita, T.; Endo, H.; Hamamoto, T.; Baba,
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(4b) Yellow solid (with greenish yellow florescence
in CHCl3); Mp: 168-170 °C; IR (KBr): 1625 (C=N), 1498
1
(C=C), 2900 cm-1 (CH aliphatic); H NMR (400 MHz,
CDCl3): d 2.43 (dd, 1H, J = 17.8 Hz, 7.4 Hz), 2.88 (s, 3H),
3.19 (dd, 1H, J = 17.8 Hz, 12.3 Hz), 5.66 (dd, 1H, J = 12.3
Hz, 7.4 Hz), 6.77 (t, 1H, J = 7.2 Hz), 6.98 (d, 1H, J = 8.1
Hz), 7.08-7.16 (m, 2H), 7.25-7.33 (m, 5H), 7.41-7.49 (m,
5H), 7.55 (s, 1H), 7.61 (dd, 1H, J = 9.1 Hz, 2.1 Hz), 7.71-
7.82 (m, 3H), 8.01 ppm (d, 1H, J = 7.8 Hz); ms: m/z 523
(M+).
10. Shibata, S. Stem Cells 1994, 12, 44.
11. Baluja, A.; Municio, A. M.; Vega, S. Chem. Ind. 1964, 3,
2053.
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(4c) Orange yellow solid (with greenish yellow
florescence in CHCl3); Mp: 160-162 °C; IR (KBr): 2914
15. Barsoum, F. F.; Hosni, H. M.; Girgis, A. S. Bioorg. Med.
Chem. 2006, 14, 3929.
1
(CH aliphatic), 1599 (C=N), 1566 cm-1 (C=C), H NMR
(400 MHz, DMSO-d6): d 2.80 (s, 3H), 3.68 (dd, 1H, J =
18.8 Hz, 8.0 Hz), 4.18 (dd, 1H, J =18.8 Hz, 12.3 Hz), 5.80
(dd, 1H, J = 12.3 Hz, 7.8 Hz), 6.88 (m, 1H), 7.98 (m, 1H),
7.00-7.45 (m, 12H), 7.50-7.60 ppm (m, 3H); ms: m/z 491
(M+).
16. Foresti, R.; Hoque, M.; Monti, D.; Green, C. J.; Motterlini,
R. J. Pharmacol. Exp. Ther. 2004, 312, 686.
17. Tomoda, H.; Ômura, S. Pharmacol. Ther. 2007, 115, 375.
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doi:10.1016/j.arabjc.2011.01.032.
(4d) Yellow solid (with greenish yellow florescence
in CHCl3); Mp: 190-192 °C; IR (KBr) cm-1: 1628 (C=N),
1
1479 (C=C), 2923 (CH aliphatic); H NMR (400 MHz,
21. Mamolo, G. M.; Zampieri, D.; Falagiani, V.; Vio, L.; Banfi,
E. Farmaco 2001, 56, 593.
CDCl3): d 2.50 (dd, 1H, J = 17.5 Hz, 6.9 Hz), 2.88 (s, 3H),
2.97 (dd, 1H, J = 12.0 Hz, 17.5 Hz), 5.22 (dd, 1H, J = 12.0
Hz, 6.9 Hz), 6.77-6.87 ppm (m, 3H), 7.01-7.41 (m, 10H),
7.49 (s, 1H), 7.63 (d, 1H, J = 8.7 Hz), 8.03 (d, 1H, J = 8.7
Hz); ms: m/z 479 (M+).
22. Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth,
J. R.; Coffen, D. L. Tetrahedron 1998, 54, 16, 4085.
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