One-pot three-component mild synthesis of 2-Aryl-3-(9-alkylcarbazol-3-yl) thiazolidin-4-ones

Article abstract of DOI:10.1002/jhet.1047

A series of novel 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones were synthesized by one-pot three-component reactions of 3-amino-9-alkylcarbazoles, aromatic aldehydes, and 2-mercaptoacetic acid by using dicyclohexylcarbodiimide (DCC) as a cyclizing agent in dry diethyl ether at room temperature. This protocol has advantages of mild condition, short reaction time, high yield, and simple work-up procedure.

Full text of DOI:10.1002/jhet.1047

1458
One-Pot Three-Component Mild Synthesis of
2-Aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones
Vol 49
*
Zheng Li, Anguo Zhu, and Jingya Yang
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu
730070, People’s Republic of China
*
E-mail: lizheng@nwnu.edu.cn
Received April 11, 2011
DOI 10.1002/jhet.1047
View this article online at wileyonlinelibrary.com.
A series of novel 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones were synthesized by one-pot three-
component reactions of 3-amino-9-alkylcarbazoles, aromatic aldehydes, and 2-mercaptoacetic acid by using
dicyclohexylcarbodiimide (DCC) as a cyclizing agent in dry diethyl ether at room temperature. This protocol
has advantages of mild condition, short reaction time, high yield, and simple work-up procedure.
J. Heterocyclic Chem., 49, 1458 (2012).
INTRODUCTION
RESULTS AND DISCUSSION
Thiazolidinones are important heterocyclic compounds
with a wide range of pharmaceutical and biological activi-
ties, such as anticancer [1], antibacterial [2], antiparasitic
[3], anti-HIV [4], anti-toxoplasma gondii [5], antitubercu-
lar [6], antioxidant [7], and anti-inflammatory [8] activities.
In addition, carbazole-involved compounds have received
increasing interest because of their unique optical proper-
ties and strong hole-transporting ability in opto-electronic
devices [9], and some important biological activities, such
as antitumor [10], antibacterial, and antifungal [11], anti-
mycobacterium tuberculosis [12], anti-HIV [13], and anti-
proliferative [14] activities. Therefore, the compounds
bearing both carbazole and thiazolidinone moieties may
be good candidates for optical materials or biologically
active chemicals.
The common synthetic routes to thiazolidinones in-
clude the reactions of a-chloroamide derivatives with
thiocyanates or isothiocyanates [15], the reactions of
thioureas with trichloromethylcarbinols [16], the reac-
tions of 1,3,4-thiadiazoles, substituted benzaldehydes
and mercaptoacetic acid [17], and the reactions of Schiff
bases or imines with mercaptoacetic acid [18]. However,
some methods often require long reaction time and high
temperature, and the reagents used in the reactions are
usually corrosive and environmentally unfriendly.
In this article, we report a one-pot three-component
synthetic method for novel carbazole-based thiazolidinones
by using dicyclohexylcarbodiimide (DCC) as a cyclizing
agent in dry diethyl ether at room temperature.
The required 3-amino-9-alkylcarbazoles were prepared
according to literature methods [19], [20] (Scheme 1).
The reactions of carbazole with bromoalkanes in acetone
in the presence of potassium hydroxide first gave 9-alkyl-
carbazoles in high yield. 9-Alkylcarbazoles on treatment
with nitric acid in the solution of 1,2-dichloroethane at
0ꢀC afforded 3-nitro-9-alkylcarbazols in high selectivity
(no 3,6-dinitrocarbazoles by-product were observed). 3-
Nitro-9-alkylcarbazols were further reduced with tin and
hydrochloric acid to give 3-amino-9-alkylcarbazoles.
In order to explore the one-pot three-component
reactions of 3-amino-9-alkylcarbazoles, aromatic alde-
hydes and 2-mercaptoacetic acid, and mild synthesis of
carbazole-based thiazolidinones, 3-amino-9-ethylcarbazole,
benzaldehyde and 2-mercaptoacetic acid were selected
as substrates to conduct the reaction (Scheme 1). It was
found that the optimal yield for the reaction was obtained
by using 1 mmol of 3-amino-9-ethylcarbazole reacting
with 1.2 mmol of benzaldehyde and 1.2 mmol of 2-
mercaptoacetic acid. DCC was found to be an important
promoting agent for the reaction, which was converted
into insoluble solid, N,N0-dicyclohexylurea (DCU), after
the reaction and could be easily removed from the reac-
tion system only by filtration. In addition, the solvent
played an important role in the reaction. Many aprotic
solvents could be utilized in three-component reaction,
among them diethyl ether gave the best result (Table 1).
To explore the generality and scope of the one-pot three-
component reactions, and synthesis of a series of novel
© 2012 HeteroCorporation

November 2012
One-Pot Three-Component Mild Synthesis of
2-Aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones
1459
Scheme 1
2-aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones (1a–m),
different 3-aminocabazoles and different aromatic aldehydes
as substrates were examined under optimal conditions
(Table 2). It was found that 9-ethyl and 9-butyl substituted
3-aminocarbazoles both were efficient for the reactions.
Various aromatic aldehydes including nitro-, methoxy-,
hydroxyl-, and dimethylamino- substituted benzaldehydes
and heterocyclic aldehyde, furanaldehyde, were all suitable
to the reactions. The electron-withdrawing and electron-
donating groups on aromatic rings had no obvious effect
on the yield of reactions. However, 4-(dimethylamino)benz-
aldehyde and furanaldehyde showed the slightly weaker
activities for the reactions, and gave the corresponding
products in slightly lower yield.
2. Presumably, condensation of 3-amino-9-alkylcarbazoles
with aldehydes in the presence of DCC by releasing DCU
first generates Schiff base intermediates A. The Schiff base
A subsequently reacts with 2-mercaptoacetic acid by addi-
tion reaction to form intermediate B. Subsequently, the in-
termediate B in the presence of DCC undergoes the
intramolecular dehydration by eliminating DCU to give
five-membered heterocyclic compounds, 2-aryl-3-(9-alkyl-
carbazol-3-yl)thiazolidin-4-ones.
In conclusion, we have developed a highly efficient one-
pot three-component method for the synthesis of a series of
new carbazole-based thiazolidinones at room temperature
in diethyl ether. This protocol has advantages of mild con-
dition, short reaction time, high yield, and simple work-up
procedure.
The resulting compounds 1a–m are highly soluble in
common organic solvents including CHC13, CH2C12,
DMSO, DMF, and EtOH. The structures of compounds
1a–m were identified by IR, 1H-NMR, 13C-NMR, and ele-
EXPERIMENTAL
1
IR spectra were recorded using KBr pellets on a Digilab FTS
3000 FTIR spectrophotometer and 1H-NMR and 13C-NMR spec-
tra on a Mercury Plus-400 instrument using CDCl3 as solvent and
Me4Si as internal standard. Elemental analyses were performed
on a Vario E1 elemental analysis instrument. Melting points
were observed in an electrothermal melting point apparatus.
mental analyses. The H-NMR spectra of compounds 1a–
m in CDCl3 show CH group single proton peaks of thiazo-
lidin-4-one at d 6.08–6.13 ppm and CH2 group two double
proton peaks of thiazolidin-4-one at d 3.92–4.11 ppm. The
IR spectra of compounds 1a–m show characteristic absorp-
tions at 1680–1688 cmꢁ1, attributable to the carbonyl
groups.
Table 2
A possible mechanism for the synthesis of 2-aryl-3-(9-
alkylcarbazol-3-yl)thiazolidin-4-ones is shown in Scheme
Synthesis of 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones.
Compd. R1
R2
Yield (%)a m.p. (ꢀC)
Table 1
1a
1b
1c
1d
1e
1f
1g
1h
1i
Et
Et
Et
Et
Et
Et
C6H5-
92
90
96
90
95
81
95
90
88
94
80
94
82
186–188
146–148
150–152
168–170
74–76
144–146
122–124
70–72
172–174
100–102
110–112
60–62
The effect of solvents on the yield of the reaction product.a
4-NO2C6H4-
3-NO2C6H4-
4-OHC6H4-
3-CH3O-4-OHC6H3-
Furan-2-
Entry
Solvent
Yield (%)b
1
2
3
4
5
CH2Cl2
Et2O
THF
PhMe
Free
87
92
90
88
60
n-Bu C6H5-
n-Bu 4-CH3OC6H4-
n-Bu 4-OHC6H4-
n-Bu 4-NO2C6H4-
n-Bu 4-(CH3)2NC6H4-
n-Bu 3-CH3O-4-OHC6H3-
n-Bu Furan-2-
1j
1k
1l
aReaction condition: 1 mmol of 3-amino-9-ethylcarbazole, 1.2 mmol of
benzaldehyde, 1.2 mmol of 2-mercaptoacetic acid, and 2 mmol of DCC in
20 mL of solvent or no solvent.
1m
124–126
bYields refer to the isolated products.
aYields refer to the isolated products.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

1460
Z. Li, A. Zhu, and J. Yang
Vol 49
Scheme 2
1d. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1683 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 9.43 (br, 1H, OH), 7.23–7.83 (m, 9H, Ph-H), 6.65–
6.68 (m, 2H, Ph-H), 6.13 (s, 1H, CH), 4.24–4.28 (q, J = 6.8 Hz,
2H, CH2), 4.05–4.09 (d, J = 16 Hz, 2H, CH), 3.93–3.97 (d, J =
16 Hz, 2H, CH), 1.37 (t, J = 6.8 Hz, 3H). 13C-NMR (100 MHz,
CDCl3): d 171.1, 156.9, 134.0, 131.8, 130.1, 127.5, 127.2,
127.1, 127.0, 126.4, 124.2, 123.2, 122.3, 120.3, 119.3, 118.1,
108.2, 108.1, 66.8, 37.7, 33.3, 13.8. Analysis calculated for
C23H20N2O2S: C, 71.11; H, 5.19; N, 7.21. Found: C, 71.05; H,
5.21; N, 7.16.
1e. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1688 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 9.83 (br, 1H, OH), 7.18–7.89 (m, 9H, Ph-H), 6.73–
6.76 (m, 1H, Ph-H), 6.09 (s, 1H, CH), 4.21–4.26 (q, J = 6.4 Hz,
2H, CH2), 4.02–4.06 (d, J = 16 Hz, 1H, CH), 3.92–3.96 (d, J =
16 Hz, 1H, CH), 3.70 (s, 3H, OCH3), 1.39 (t, J = 6.4 Hz, 3H,
CH3). 13C-NMR (100 MHz, CDCl3): d 171.0, 152.4, 147.1,
134.0, 131.8, 126.5, 126.2, 126.1, 125.5, 123.5, 123.2, 122.3,
120.1, 119.2, 118.4, 116.5, 114.3, 108.9, 108.8, 66.7, 56.9,
37.6, 33.5, 13.5. Analysis calculated for C24H22N2O3S: C,
68.88; H, 5.30; N, 6.69. Found: C, 68.94; H, 5.31; N, 6.65.
1f. This compound was obtained as white solid (EtOH). IR
9-Ethylcarbazole, 9-butylcarbazole [19], 3-nitro-9-ethylcarba-
zole, 3-nitro-9-butylcarbazole, 3-amino-9-ethylcarbazole, and 3-
amino-9-butylcarbazole [20] were prepared according to literature
procedures.
Synthesis of 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-
ones. The mixture of 3-amino-9-alkylcarbazoles (1 mmol) and
aromatic aldehydes (1.2 mmol) in 20 mL of dry diethyl ether was
stirred for 20 min, then 2-mercaptoacetic acid (1.2 mmol) and
DCC (2 mmol) were added, and the reaction system was stirred
for another 2 h at room temperature. The completion of the
reactions was monitored by TLC. Then the solid was removed by
filtration, and the liquor was washed with saturated sodium
carbonate and water, and dried with anhydrous magnesium
sulfate. After the solvent was evaporated off, the residue was
recrystallized from ethanol to give products. Analytical data for
compounds 1a–m are given below.
1
(potassium bromide): 1680 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.15–7.80 (m, 8H, Ph-H), 6.43–6.46 (m, 1H, Fu-H),
6.24–6.26 (m, 1H, Fu-H), 6.12 (s, 1H, CH), 4.21–4.24 (q, J =
6.4 Hz, 2H, CH2), 4.02–4.04 (d, J = 16 Hz, 1H, CH), 3.90–3.94
(d, J = 16 Hz, 1H, CH), 1.33 (t, J = 6.4 Hz, 3H, CH3). 13C-
NMR (100 MHz, CDCl3): d 171.3, 151.5, 142.1, 134.2, 134.0,
128.4, 126.2, 125.1, 121.7, 121.4, 119.8, 112.6, 110.6, 110.2,
109.9, 108.5, 107.0, 66.0, 37.5, 33.7, 13.3. Analysis calculated
for C21H18N2O2S: C, 69.59; H, 5.01; N, 7.73. Found: C, 69.55;
H, 5.03; N, 7.69.
1a. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1684 (C═O) cmꢁ1. H-NMR (400 MHz,
1g. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1683 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.15–7.96 (m, 12H, Ph-H), 6.12 (s, 1H, CH), 4.27–
4.29 (q, J = 6.8 Hz, 2H, CH2), 4.06–4.10 (d, J = 16 Hz, 1H,
CH), 3.94–3.98 (d, J = 16 Hz, 1H, CH), 1.37 (t, J = 6.8 Hz,
3H, CH3). 13C-NMR (100 MHz, CDCl3): d 171.3, 140.3, 139.8,
138.7, 128.8, 128.7, 128.6, 127.3, 126.0, 124.3, 123.2, 122.5,
120.5, 119.0, 118.8, 108.8, 108.6, 66.6, 37.6, 33.5, 13.7.
Analysis calculated for C23H20N2OS: C, 74.16; H, 5.41; N,
7.52. Found: C, 74.19; H, 5.40; N, 7.49.
CDCl3): d 7.15–7.80 (m, 12H, Ph-H), 6.11 (s, 1H, CH), 4.23–
4.26 (t, J = 6.8 Hz, 2H, CH2), 4.03–4.07 (d, J = 16 Hz, 1H,
CH), 3.93–3.97 (d, J = 16 Hz, 1H, CH), 1.76–1.80 (m, 2H,
CH2), 1.35–1.38 (m, 2H, CH2), 0.89–0.93 (t, J = 6.4 Hz, 3H,
CH3). 13C-NMR (100 MHz, CDCl3): d 171.5, 140.1, 139.5,
138.2, 128.5, 128.4, 128.3, 127.1, 126.5, 124.8, 123.5, 122.8,
120.2, 119.3, 118.4, 108.5, 108.2, 66.0, 42.6, 33.2, 30.7, 20.2,
13.5. Analysis calculated for C25H24N2OS: C, 74.97; H, 6.04;
N, 6.99. Found: C, 74.89; H, 6.03; N, 6.93.
1b. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1688 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.17–8.07 (m, 11H, Ph-H), 6.10 (s, 1H, CH), 4.24–
4.28 (q, J = 6.4 Hz, 2H, CH2), 4.07–4.11 (d, J = 16 Hz, 1H,
CH), 3.95–3.99 (d, J = 16 Hz, 1H, CH), 1.36 (t, J = 6.4 Hz,
3H). 13C-NMR (100 MHz, CDCl3): d 171.2, 146.3, 145.3,
138.2, 127.8, 127.7, 127.6, 127.3, 126.0, 124.3, 123.5, 122.8,
120.6, 119.5, 118.5, 108.4, 108.1, 66.7, 37.8, 33.4, 13.7.
Analysis calculated for C23H19N3O3S: C, 66.17; H, 4.59; N,
10.07. Found: C, 66.12; H, 4.57; N, 10.03.
1h. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1688 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.95–7.97 (m, 1H, Ph-H), 7.78 (s, 1H, Ph-H), 7.11–
7.44 (m, 7H, Ph-H), 6.77–6.79 (m, 2H, Ph-H), 6.09 (s, 1H,
CH), 4.20–4.23 (t, J = 6.8 Hz, 2H, CH2), 4.04–4.08 (d, J = 16
Hz, 1H, CH), 3.94–3.98 (d, J = 16 Hz, 1H, CH), 3.72 (s, 3H,
OCH3), 1.77–1.81 (m, 2H, CH2), 1.36–1.39 (m, 2H, CH2),
0.90–0.94 (t, J = 6.4 Hz, 3H, CH3). 13C-NMR (100 MHz,
CDCl3): d 171.2, 159.6, 140.5, 138.9, 131.2, 128.5, 128.3,
125.7, 124.1, 122.8, 122.1, 120.2, 118.6, 118.5, 113.7, 108.7,
108.5, 66.0, 54.9, 42.6, 33.3, 30.7, 20.2, 13.5. Analysis
calculated for C26H26N2O2S: C, 72.53; H, 6.09; N, 6.51. Found:
C, 72.58; H, 6.10; N, 6.54.
1c. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1680 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.19–8.08 (m, 11H, Ph-H), 6.09 (s, 1H, CH), 4.22–
4.26 (q, J = 6.8 Hz, 2H, CH2), 4.08–4.12 (d, J = 16 Hz, 2H,
CH), 3.96–4.00 (d, J = 16 Hz, 2H, CH), 1.34 (t, J = 6.8 Hz,
3H, CH3). 13C-NMR (100 MHz, CDCl3): d 171.2, 146.6, 140.8,
139.5, 138.3, 127.5, 127.2, 127.1, 127.0, 126.5, 124.5, 124.0,
123.2, 122.3, 120.1, 119.2, 118.4, 108.5, 108.5, 66.3, 37.3,
33.2, 13.9. Analysis calculated for C23H19N3O3S: C, 66.17; H,
4.59; N, 10.07. Found: C, 66.21; H, 4.58; N, 10.04.
1i. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1685 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 9.38 (br, 1H, OH), 7.23–7.83 (m, 9H, Ph-H), 6.63
(m, 2H, Ph-H), 6.11 (s, 1H, CH), 4.10–4.16 (t, J = 6.4 Hz, 2H,
CH2), 4.04–4.08 (d, J = 16 Hz, 1H, CH), 3.93–3.97 (d, J = 16
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2012
One-Pot Three-Component Mild Synthesis of
2-Aryl-3-(9-alkylcarbazol-3-yl)thiazolidin-4-ones
1461
Hz, 1H, CH), 1.78–1.83 (m, 2H, CH2), 1.35–1.37 (m, 2H, CH2),
0.90–0.93 (t, J = 6.4 Hz, 3H, CH3). 13C-NMR (100 MHz,
CDCl3): d 171.3, 156.5, 134.2, 131.2, 130.0, 127.8, 127.3,
127.1, 127.5, 126.2, 124.1, 123.2, 122.5, 120.5, 119.4, 118.7,
108.8, 108.1, 66.2, 42.5, 33.1, 30.4, 20.5, 13.4. Analysis
calculated for C25H24N2O2S: C, 72.09; H, 5.81; N, 6.73. Found:
C, 72.03; H, 5.82; N, 6.69.
Acknowledgments. The authors thank the National Natural Science
Foundation of China (20772096) and Key Laboratory of Polymer
Materials of Gansu Province for financial support of this work.
REFERENCES AND NOTES
1j. This compound was obtained as white solid (EtOH). IR
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1
(potassium bromide): 1688 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.19–8.08 (m, 11H, Ph-H), 6.08 (s, 1H, CH), 4.27–
4.29 (t, J = 6.8 Hz, 2H, CH2), 4.05–4.09 (d, J = 16 Hz, 2H,
CH), 3.95–3.99 (d, J = 16 Hz, 2H, CH), 1.75–1.80 (m, 2H,
CH2), 1.35 (m, 2H, CH2), 0.89–0.92 (t, J = 6.8 Hz, 3H). 13C-
NMR (100 MHz, CDCl3): d 171.2, 146.5, 145.8, 139.2, 138.1,
127.9, 127.8, 127.5, 126.5, 124.7, 123.9, 122.5, 120.3, 119.8,
118.9, 108.7, 108.5, 66.7, 42.9, 33.5, 30.8, 20.5, 13.6. Analysis
calculated for C25H23N3O3S: C, 67.40; H, 5.20; N, 9.43. Found:
C, 67.35; H, 5.19; N, 9.39.
1k. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1687 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 6.64–7.90 (m, 11H, Ph-H), 6.10 (s, 1H, CH), 4.17–
4.19 (t, J = 6.4 Hz, 2H, CH2), 4.04–4.08 (d, J = 16 Hz, 2H,
CH), 3.94–3.98 (d, J = 16 Hz, 2H, CH), 3.06 (s, 6H, NCH3),
1.75–1.78 (m, 2H, CH2), 1.38 (m, 2H, CH2), 0.87–0.90 (t, J =
6.4 Hz, 3H, CH3). 13C-NMR (100 MHz, CDCl3): d 171.2, 149.5,
139.8, 134.1, 128.7, 128.4, 127.8, 127.5, 125.1, 121.7, 121.5,
119.8, 112.8, 109.9, 109.6, 108.5, 103.3, 66.7, 42.9, 40.2, 33.5,
32.6, 20.5, 13.6. Analysis calculated for C27H29N3OS: C, 73.10;
H, 6.59; N, 9.47. Found: C, 73.18; H, 6.67; N, 9.44.
1l. This compound was obtained as white solid (EtOH). IR
1
(potassium bromide): 1688 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 9.80 (br, 1H), 7.34–7.85 (m, 9H, Ph-H), 6.73 (m,
1H, Ph-H), 6.12 (s, 1H, CH), 4.22–4.25 (t, J = 6.8 Hz, 2H,
CH2), 4.05–4.09 (d, J = 16 Hz, 2H, CH), 3.95–3.99 (d, J = 16
Hz, 2H, CH), 3.70 (s, 3H, OCH3), 1.74–1.75 (m, 2H, CH2),
1.32–1.36 (m, 2H, CH2), 0.89–0.90 (t, J = 6.8 Hz, 3H, CH3).
13C-NMR (100 MHz, CDCl3): d 171.0, 147.6, 147.0, 134.5,
131.2, 126.5, 126.3, 126.0, 125.2, 123.7, 123.6, 122.3, 120.4,
119.6, 118.8, 114.3, 112.5, 108.9, 108.4, 66.0, 54.3, 42.6, 33.5,
30.6, 20.4, 13.8. Analysis calculated for C26H26N2O3S: C,
69.93; H, 5.87; N, 6.27. Found: C, 69.85; H, 5.85; N, 6.30.
1m. This compound was obtained as white solid (EtOH). IR
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K. R.; Franzblau, S. G.; Knolker, H. J. Chemmedchem 2006, 1, 812.
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M.; Lee, K. H. Bioorg Med Chem Lett 1999, 9, 119.
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Boykin, D. W. Bioorg Med Chem Lett 2007, 17, 1193; (b) Liger, F.;
Popowycz, F.; Besson, T.; Picot, L. Bioorg Med Chem 2007, 15, 5615.
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44, 35; (b) Dains, F. B.; Eberly, F. J Am Chem Soc 1933, 55, 3859.
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1
(potassium bromide): 1680 (C═O) cmꢁ1. H-NMR (400 MHz,
CDCl3): d 7.17–7.82 (m, 8H, Fu-H), 6.48 (m, 1H, Fu-H), 6.27
(m, 1H, Fu-H), 6.10 (s, 1H, CH), 4.26–4.29 (t, J = 6.4 Hz, 2H,
CH2), 4.02–4.06 (d, J = 16 Hz, 2H, CH), 3.92–3.96 (d, J = 16
Hz, 2H, CH), 1.74–1.78 (m, 2H, CH2), 1.33–1.36 (m, 2H,
CH2), 0.87–0.90 (t, J = 6.4 Hz, 3H, CH3). 13C-NMR (100
MHz, CDCl3): d 171.3, 151.8, 141.8, 133.9, 128.2, 126.1,
125.7, 121.9, 121.6, 119.5, 112.9, 112.2, 110.5, 110.2, 109.7,
108.9, 107.0, 66.0, 42.8, 37.9, 33.6, 20.6, 13.7. Analysis
calculated for C23H22N2O2S: C, 70.74; H, 5.68; N, 7.17. Found:
C, 70.79; H, 5.70; N, 7.14.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet