One-pot three-component synthesis of benzo[f]thiopyrano[3,4-b]quinolin- 11(8H)-one derivatives

Article abstract of DOI:10.1002/jhet.1727

A series of novel benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-one derivatives were synthesized via the reaction of aryl aldehyde, 2H-thiopyran-3,5(4H,6H)- dione, and β-naphthylamine in glacial acetic acid. This protocol features mild reaction conditions, hig

Full text of DOI:10.1002/jhet.1727

702
One-Pot Three-Component Synthesis of Benzo[f]thiopyrano[3,4-b]quinolin-
11(8H)-one Derivatives
Vol 51
a
a
b
a
a
a
a
*
Chenxia Yu, Honghong Zhang, Changsheng Yao, Tuanjie Li, Bingbin Qin, Jun Lu, and Donglin Wang
aSchool of Chemistry and Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials,
Jiangsu Normal University, Xuzhou, Jiangsu 221116, People’s Republic of China
bSchool of Chemistry and Chemical Engineering, Key Laboratory of Biotechnology on Medical Plant, Jiangsu Normal
University, Xuzhou, Jiangsu 221116, People’s Republic of China
*
E-mail: csyao@jsnu.edu.cn
Received November 11, 2011
DOI 10.1002/jhet.1727
Published online 3 December 2013 in Wiley Online Library (wileyonlinelibrary.com).
O
Ar
O
NH2
HOAc
ArCHO
+
+
O
S
S
N
H
1
2
3
4
A series of novel benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-one derivatives were synthesized via the
reaction of aryl aldehyde, 2H-thiopyran-3,5(4H,6H)-dione, and b-naphthylamine in glacial acetic acid. This
protocol features mild reaction conditions, high yields, and short reaction time.
J. Heterocyclic Chem., 51, 702 (2014).
INTRODUCTION
RESULTS AND DISCUSSION
Thiopyran and fused thiopyran are among the most
frequently found heterocyclic skeletons. Their derivatives
are indispensible to agrochemistry and pharmacological
chemistry because of their potential biological properties,
such as weed control [1] and fungicidal activity [2]. Com-
pounds containing the quinoline skeletons are known to
display many biological and pharmaceutical activities,
such as psychotropic, antiallergenic, anti-inflammatory,
and estrogenic activities [3–5]. So the synthesis of these
compounds has drawn considerable attention of a number
of chemists. However, many of developed methods for
synthesizing quinoline derivatives so far suffer from some
disadvantages including harsh reaction conditions, multi-
step reaction, poor stereoselectivity, and the use of metal
(or metal salt) catalysts and expensive reagents. To the best
of our knowledge, there has been no report on the synthesis
of benzo[f]thiopyrano[3,4-b]quinolin derivatives. Given
the biological importance of scaffolds of thiopyran and
quinoline, to develop a simple and convenient approach
for the synthesis of these fused S,N-containing compounds
is still necessary. In addition, multicomponent reactions
(MCRs) have many advantages, for example, atom econ-
omy, straightforward reaction condition, and generating
the diversified compound library powerfully [6–10]. So
far, many organic transformations have been reported to
proceed well in the version of MCRs [11–15]. To continue
our work on the synthesis heterocyclic compounds via
MCRs [16–18], herein we shall report an efficient and easy
method to synthesize benzo[f]thiopyrano[3,4-b]quinolin
derivatives 4 via the reaction of aldehyde 1, 2H-thiopyran-
3,5(4H,6H)-dione 2, and b-naphthylamine 3 in glacial acetic
acid (Scheme 1).
The effect of solvent on the reaction was initially examined
by reacting 2H-thiopyran-3,5(4H,6H)-dione 2 (1 mmol) and
b-naphthylamine 3 (1 mmol) with 4-bromobenzaldehyde 1a
(1 mmol). It was found that the reaction in glacial acetic acid
(Table 1, entry 1) showed higher yield than other counterparts.
So, glacial acetic acid was used as the optimal solvent to
synthesize the target compounds.
To screen the optimal temperature, the previous reaction
was carried out in glacial acetic acid at 15, 25, 35, 45, and
55ꢀC, and product 4a was obtained in 50, 82, 75, 60, and
56% yields (Table 2, entries 1–5), respectively. As shown
in Table 2, 25ꢀC was the preferable temperature for this
reaction from the viewpoint of yield.
With optimized reaction conditions, a series of benzo[f]
thiopyrano[3,4-b]quinolin-11(8H)-ones were synthesized
successfully. As shown in Table 3, the reaction at 25ꢀC
in glacial acetic acid gave the corresponding products in
moderate to good yields. The results revealed that not only
electron-rich aryl aldehyde (such as a methoxy group) but
also electron-deficient aryl aldehyde (such as a nitro group,
halogen) in the multicomponent reaction afforded the
corresponding products efficiently under the same condi-
tions. Therefore, we concluded that the electronic nature
of substituents of the aromatic aldehyde had no significant
effect on the reaction. Furthermore, hetereoaryl aldehyde
could also participate in the three-component reaction and
give the desired product in high yield (Table 3, entry 14).
However, when the aliphatic aldehydes were applied to
this reaction, no desired product was obtained.
According to reference [19], a possible reaction pathway
was proposed for the formation of the products 4 (Scheme 2).
Initially, the condensation between aryl aldehyde and
© 2013 HeteroCorporation

May 2014
One-Pot Three-Component Synthesis of Benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-ones
703
Scheme 1
Scheme 2
Table 1
Solvent effect on the synthesis of 4a.
Entry
Solvent
Temp. (ꢀC)
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
HOAc
CHCl3
CH2Cl2
MeOH
EtOH
CH3CN
DMF
25
25
25
25
25
25
25
25
8
8
8
8
8
8
8
8
82
50
43
65
73
70
60
70
Solvent free
In order to verify the aforementioned reaction mechanism,
we synthesized the Schiff base 5g via the condensation of
4-chlorobenzaldehyde and b-naphthylamine under the
same conditions. It could react with 2 to give the expected
product 4g successfully (Scheme 3). This fact provided the
proof in support of the reaction pathway.
Table 2
Temperature optimization for the synthesis of 4a in glacial acetic acid.
Entry
Temp. (ꢀC)
Time (h)
Yield (%)
1
2
3
4
5
15
25
35
45
55
8
8
8
8
8
50
82
75
60
56
All of the compounds were characterized by HRMS,
1
FTIR, and H-NMR.
In summary, we have developed a simple and efficient
method for the synthesis of a series of novel benzo[f]thio-
pyrano[3,4-b]quinolin-11(8H)-ones via a one-pot multi-
component reaction in acidic media. This procedure
features short reaction time, generally good to excellent
yields, easily available starting materials, and operational
simplicity (only one pot).
Table 3
Synthesis of compound 4.
Time Yield
Entry Compound
Ar
4-BrC6H4
2-BrC6H4
2-FC6H4
3-FC6H4
4-FC6H4
3-ClC6H4
4-ClC6H4
3,4-Cl2C6H3
3-CH3OC6H4
3,4,5-(CH3O)3C6H2
4-CH3C6H4
3-NO2C6H4
4-NO2C6H4
Thiophene-2-yl
(h)
(%) mp (ꢀC)
1
2
3
4
5
6
7
8
9
10
11
12
13
14
4a
4b
4c
4d
4e
4f
4g
4h
4i
8
9
7
7.5
8
9
8
9
6
5
82
78
80
81
77
78
79
75
83
85
80
75
73
82
>300
>300
>300
291–293
>300
>300
EXPERIMENTAL
Common reagents and materials were purchased from com-
mercial sources and purified by recrystallization or distillation.
IR spectra were recorded on a TENSOR 27 spectrophotometer
(Bruker, Ettlingen, Germany) in KBr pellet and are reported in
terms of frequency of absorption (cmÀ1). NMR spectra were
recorded on a Bruker (Switzerland) AV-400; data for 1H are
reported as follows: chemical shift (ppm), integration, multiplicity
>300
>300
285–287
284–286
>300
296–298
297–298
>300
4j
4k
4l
6
9
9
7
4m
4n
Scheme 3
b-naphthylamine gave Schiff base 5. The addition between 5
and 2 then afforded the intermediate 6, which was decom-
posed into 3 and 8. The Michael addition between 3 and
8 generated intermediate 9, which were transformed into
the ultimate compounds 4 through the intramolecular cycli-
zation and dehydration.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

704
C. Yu, H. Zhang, C. Yao, T. Li, B. Qin, J. Lu, and D. Wang
Vol 51
(s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; and br,
broad), coupling constant (Hz), and number. HRMS (ESI) were de-
termined by using microTOF-QIIHRMS/MS instrument (Bruker).
General procedure for the synthesis of 12-aryl-10,12-dihydro-
7H-benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-one (4a-4n).
Aldehyde 1 (1 mmol), 2H-thiopyran-3,5(4H,6H)-dione 2 (1mmol),
b-naphthylamine 3 (1 mmol), and HOAc (10 mL) were mixed and
then stirred at 25ꢀC for 6–10h. After completion of the reaction
(monitored by TLC), the reaction mixture was poured into water.
The solid was recrystallized from DMF to give pure products 4. A
similar procedure was used in preparing the following compounds.
12-(4-Bromophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
12-(3-Chlorophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4f).
IR (KBr, n, cmÀ1): 3266,
1683, 1594, 1541, 1365, 1246, 817; 1H-NMR (400 MHz, DMSO-d6)
(d, ppm): 10.1 (s, 1H, NH), 7.93–7.96 (m, 2H, ArH), 7.84 (d,
J= 8.4 Hz, 2H, ArH), 7.44–7.48 (m, 1H, ArH), 7.33–7.37 (m, 2H,
ArH), 7.13–7.21 (m, 2H, ArH), 7.09–7.11 (m, 1H, ArH), 5.94 (s, 1H,
CH), 3.95 (d, J= 16.8 Hz, 1H, CH2), 3.54 (d, J= 16.0 Hz, 2H, CH2),
3.10 (d, J= 16.0 Hz, 1H, CH2). HRMS (ESI): m/z Calcd for
C22H15ClNOS [M À H]À 378.0714, found: 378.0750.
12-(4-Chlorophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4g).
IR (KBr, n, cmÀ1): 3276,
1
2341, 1577, 1493, 1370, 1243, 1138, 811, 750, 521; H-NMR
(400 MHz, DMSO-d6) (d, ppm): 10.06 (s, 1H, NH), 7.92 (d,
J = 8.4 Hz, 1H, ArH), 7.82–7.84 (m, 2H, ArH), 7.42–7.46 (m,
1H, ArH), 7.33–7.36 (m, 2H, ArH), 7.22 (s, 4H, ArH), 5.91 (s,
1H, CH), 3.94 (d, J = 18 Hz, 1H, CH2), 3.49–3.55 (m, 2H, CH2),
3.08 (d, J = 15.6 Hz, 1H, CH2). HRMS (ESI): m/z Calcd for
C22H15ClNOS [M À H]À 378.0714, found: 378.0750.
[3,4-b]quinolin-11(8H)-one (4a).
3191, 2885, 2341, 1576, 1518, 1493, 1242, 1138, 811, 750,
518 cmÀ1 1H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.07 (s,
IR (KBr, n, cmÀ1): 3273,
;
1H, NH), 7.91 (d, J = 8.4 Hz, 1H, ArH), 7.83 (d, J = 7.2 Hz, 2H,
ArH), 7.44 (t, J = 6.8 Hz, 1H, ArH), 7.34 (t, J = 7.2 Hz, 4H,
ArH), 7.16 (d, J = 8.0 Hz, 2H, ArH), 5.89 (s, 1H, CH), 3.94 (d,
J = 16.0 Hz, 1H, CH2), 3.52 (q, J = 8.0 Hz, 2H, CH2), 3.08(d,
J = 15.6 Hz, 1H, CH2), HRMS (ESI): m/z Calcd for
C22H15BrNOS [M À H]À 420.0058, found: 420.0051.
12-(3,4-Dichlorophenyl)-10,12-dihydro-7H-benzo[f]thiopy-
rano[3,4-b]quinolin-11(8H)-one (4h).
IR (KBr, n, cmÀ1):
3269, 1593, 1579, 1519, 1495, 1365, 1240, 1207, 1189, 812,
749; 1H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.14 (s, 1H,
NH), 7.93 (d, J = 8.4 Hz, 1H, ArH), 7.84 (q, J = 4.0 Hz, 2H,
ArH), 7.40–7.46 (m, 3H, ArH), 7.35 (t, J = 8.4 Hz, 2H, ArH),
7.12 (d, J = 8.4 Hz, 1H, ArH), 5.94 (s, 1H, CH), 3.95 (d,
J = 16.4 Hz, 1H, CH2), 3.54 (d, J = 16.4 Hz, 2H, CH2), 3.11
(d, J = 16.0 Hz, 1H, CH2). HRMS (ESI): m/z Calcd for
C22H16Cl2NOS [M + H]+ 412.0324, found: 412.0296.
12-(2-Bromophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4b).
IR (KBr, n, cmÀ1): 3270,
3188, 3090, 2361, 1598, 1582, 1497, 1245, 741, 584 cmÀ1; H-
NMR (400 MHz, DMSO-d6) (d, ppm): 10.12 (s, 1H, NH), 8.29
(d, J = 8.4 Hz, 1H, ArH), 7.80–7.83 (m, 2H, ArH), 7.46 (q,
J = 7.6 Hz, 2H, ArH), 7.28–7.36 (m, 3H, ArH), 7.16 (t,
J = 7.2 Hz, 1H, ArH), 6.95 (t, J = 7.6 Hz, 1H, ArH), 6.05 (s, 1H,
CH), 3.95 (d, J = 16.4 Hz, 1H, CH2), 3.52 (t, J = 18.4 Hz, 2H,
CH2), 3.06 (d, J = 15.6 Hz, 1H, CH2); HRMS (ESI): m/z Calcd
for C22H15BrNOS [M À H]À 420.0058, found: 420.0051.
1
12-(3-Methoxyphenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4i). IR (KBr, n, cmÀ1): 3267, 2362,
1
1580, 1519, 1508, 1468, 1103, 814, 752, 579; H-NMR (400 MHz,
DMSO-d6) (d, ppm): 9.98 (s, 1H, NH), 7.95 (d, J= 8.4 Hz, 1H, ArH),
7.81 (t, J= 8.0 Hz, 2H, ArH), 7.44 (t, J= 6.4 Hz, 1H, ArH), 7.29–7.37
(m, 2H, ArH), 7.07–7.17 (m, 2H, ArH), 6.67–6.79 (m, 2H, ArH),5.86
(s, 1H, CH), 3.94 (d, J= 16.4 Hz, 1H, CH2), 3.62 (s, 3H, OCH3),
3.45–3.56 (m, 2H, CH2), 3.07 (d, J= 15.6 Hz, 1H, CH2). HRMS
(ESI): m/z Calcd for C23H18NO2S [M-H]- 372.1058, found: 372.1042.
12-(3,4,5-Trimethoxyphenyl)-10,12-dihydro-7H-benzo[f]
12-(2-Fluorophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4c).
3193, 2341, 1622, 1592, 1494, 1372, 1242, 1136, 819,
750 cmÀ1 1H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.07 (s,
IR (KBr, n, cmÀ1): 3278,
;
1H, NH), 8.01 (d, J = 8.8 Hz, 1H, ArH), 7.80 (t, J = 9.2 Hz, 2H,
ArH), 7.48 (t, J = 8.0 Hz, 1H, ArH), 7.28–7.36 (m, 3H, ArH),
6.97–7.11 (m, 3H, ArH), 6.04 (s, 1H, CH), 3.95 (d, J = 16.4 Hz,
1H, CH2), 3.48–3.58 (m, 2H, CH2), 3.05 (d, J = 15.6 Hz, 1H,
CH2); HRMS (ESI): m/z Calcd for C22H16FNNaOS [M + Na]+
384.0834, found: 384.0806.
thiopyrano[3,4-b]quinolin-11(8H)-one (4j).
IR (KBr, n,
cmÀ1): 3274, 2343, 1581, 1520, 1493, 1468, 1364, 1248, 1237,
820, 574; 1H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.01 (s, 1H,
NH), 8.06 (d, J = 8.4 Hz, 1H, ArH), 7.83 (t, J = 8.8 Hz, 2H, ArH),
7.48 (t, J = 7.6 Hz, 1H, ArH), 7.35 (t, J = 7.6Hz, 2H, ArH), 6.51
(s, 2H, ArH), 5.90 (s, 1H, CH), 3.94 (d, J = 16.4 Hz, 1H, CH2),
3.60 (s, 6H, OCH3), 3.54 (t, J = 14.0Hz, 5H, OCH3 + CH2), 3.13
(d, J = 15.6 Hz, 1H, CH2). HRMS (ESI): m/z Calcd for
C25H24NO4S [M+ H]+ 434.1420, found: 434.1424.
12-(3-Fluorophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4d).
IR (KBr, n, cmÀ1): 3275,
2362, 2342, 1577, 1519, 1466, 1364, 1245, 817; 1H-NMR
(400 MHz, DMSO-d6) (d, ppm): 10.09 (s, 1H, NH), 7.95 (t,
J = 2.8 Hz, 2H, ArH), 7.84 (d, J = 8.8 Hz, 2H, ArH), 7.44–7.48
(m, 1H, ArH), 7.34–7.37 (m, 2H, ArH), 7.16–7.22 (m, 1H,
ArH), 7.67–7.02 (m, 2H, ArH), 5.94 (s, 1H, CH), 3.93–3.97 (m,
1H, CH2), 3.51–3.55 (m, 2H, CH2), 3.10 (d, J = 16.0 Hz, 1H,
CH2). HRMS (ESI): m/z Calcd for C22H17FNOS [M + H]+
362.1015, found: 362.1032.
12-p-Tolyl-10,12-dihydro-7H-benzo[f]thiopyrano[3,4-b]
quinolin-11(8H)-one (4k).
IR (KBr, n, cmÀ1): 3279, 2341,
1593, 1578, 1494, 1244, 1136, 814, 747, 644, 539; 1H-NMR
(400MHz, DMSO-d6) (d, ppm): 9.99 (s, 1H, NH), 7.94 (d,
J = 8.4 Hz, 1H, ArH), 7.81 (t, J = 7.6 Hz, 2H, ArH), 7.43 (t,
J = 7.6 Hz, 1H, ArH), 7.33 (t, J = 4.0 Hz, 2H, ArH), 7.10 (d,
J = 8.0 Hz, 2H, ArH), 6.94 (d, J = 8.0Hz, 2H, ArH), 5.86 (s, 1H,
CH), 3.93 (d, J = 16.4Hz, 1H, CH2), 3.45–3.56 (m, 2H, CH2),
3.06 (d, J = 16.0Hz, 1H, CH2), 2.14 (s, 3H, CH3). HRMS (ESI):
m/z Calcd for C23H18NOS [M À H]À 356.1109, found: 356.1121.
12-(3-Nitrophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
12-(4-Fluorophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4e).
IR (KBr, n, cmÀ1): 3264,
3177, 2360, 2340, 1594, 1581, 1491, 1367, 1239, 1159, 838, 820,
1
746, 523; H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.06 (s, 1H,
NH), 7.94 (d, J= 8.4 Hz, 1H, ArH), 7.84–7.81 (m, 2H, ArH),
7.46–7.42 (m, 1H, ArH), 7.36–7.32 (m, 2H, ArH), 7.26–7.22 (m,
2H, ArH), 7.01–6.96 (m, 2H, ArH), 5.93 (s, 1H, CH), 3.95 (d,
J= 16.8, 1H, CH2), 3.55 (d, J= 4.8 Hz, 1H, CH2), 3.51 (d,
J=6.0Hz, 1H ,CH2), 3.09 (d, J= 16.0 Hz, 1H, CH2). HRMS (ESI):
m/z Calcd for C22H15FNOS [M À H]À 360.0853, found: 360.0858.
[3,4-b]quinolin-11(8H)-one (4l).
IR (KBr, n, cmÀ1): 3279,
2340, 1608, 1586, 1524, 1469, 1346, 1193, 1019, 810, 687;
1H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.19 (s, 1H, NH),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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One-Pot Three-Component Synthesis of Benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-ones
705
REFERENCES AND NOTES
8.04 (d, J = 2.0 Hz, 1H, ArH), 7.91–7.95 (m, 2H, ArH), 7.87 (t,
J = 8.8 Hz, 2H, ArH), 7.67 (d, J = 8.0 Hz, 1H, ArH), 7.43–7.51
(m, 2H, ArH), 7.34–7.44 (m, 2H, ArH), 6.07 (s, 1H, CH), 3.96
(d, J = 16.8 Hz, 1H, CH2), 3.54 (t, J = 16.4 Hz, 2H, CH2), 3.10
(d, J = 15.6 Hz, 1H, CH2). HRMS (ESI): m/z Calcd for
C22H17N2O3S [M + H]+ 389.0954, found: 389.0978
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12-(4-Nitrophenyl)-10,12-dihydro-7H-benzo[f]thiopyrano
[3,4-b]quinolin-11(8H)-one (4m). IR (KBr, n, cmÀ1): 3266,
1594, 1579, 1519, 1468, 1369, 1346, 1208, 1112, 829, 749; 1H-
NMR (400 MHz, DMSO-d6) (d, ppm): 10.18 (s, 1H, NH), 8.05 (d,
J= 8.4 Hz, 2H, ArH), 7.91 (d, J= 8.8 Hz, 1H, ArH), 7.85 (t,
J= 8.0 Hz, 2H, ArH), 7.42–7.50 (m, 3H, ArH), 7.36 (q, J=8.4Hz,
2H, ArH), 6.05 (s, 1H, CH), 3.97 (d, J= 16.8 Hz, 1H, CH2), 3.54 (d,
J= 17.6 Hz, 2H, CH2), 3.09 (d, J= 16.0 Hz, 1H, CH2). HRMS (ESI):
m/z Calcd for C22H17N2O3S [M+H]+ 389.0954, found: 389.0960
12-(Thiophen-2-yl)-10,12-dihydro-7H-benzo[f]thiopyrano
[6] Zhu, J.; Bienayme, H. Multicomponent Reactions; Wiley-
VCH: Weinheim, Germany, 2005.
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[3,4-b]quinolin-11(8H)-one (4n).
IR (KBr, n, cmÀ1): 3266,
2361, 1597, 1582, 1494, 1469, 1365, 1236, 1185, 971, 814,
715; 1H-NMR (400 MHz, DMSO-d6) (d, ppm): 10.14 (s, 1H,
NH), 8.00 (d, J = 8.4 Hz, 1H, ArH), 7.80–7.91 (m, 2H, ArH),
7.51 (t, J = 7.2 Hz, 1H, ArH), 7.39 (t, J = 7.6 Hz, 1H, ArH), 7.31
(d, J = 8.4 Hz, 1H, ArH), 7.15 (d, J = 4.8 Hz, 1H, ArH), 6.74 (t,
J = 3.2 Hz, 1H, ArH), 6.57 (d, J = 2.8 Hz, 1H, ArH), 6.19 (s, 1H,
CH), 3.96 (d, J = 16.8 Hz, 1H, CH2), 3.54 (t, J = 14.4 Hz, 2H,
CH2), 3.15 (d, J = 16.0 Hz, 1H, CH2). HRMS (ESI): m/z Calcd
for C20H14NOS2 [M À H]À 348.0517 found: 348.0488.
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Acknowledgments. We are grateful for the financial support by A
Project Funded by the Priority Academic Program Development of
Jiangsu Higher Education Institutions, the Major Basic
Research Project of the Natural Science Foundation of the
Jiangsu Higher Education Institutions (09KJA430003), Natural
Science Foundation of Xuzhou City (XM09B016), Graduate
Foundation of Xuzhou Normal University (2010YLB029), and
Qing Lan Project (08QLT001).
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet