Improved and efficient synthesis of chromeno[4,3-d]pyrazolo [3,4-b]pyridin-6(3H)-ones and their fluorescence properties

Article abstract of DOI:10.1002/jhet.2104

A series of chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one derivatives was easily and efficiently synthesized by the reaction of 2H-chromen-2-ones with pyrazol-5-amines catalyzed by CuCl₂·2H₂O in ethanol. This protocol has the advan

Full text of DOI:10.1002/jhet.2104

1036
Improved and Efficient Synthesis of Chromeno[4,3-d]pyrazolo [3,4-b]
pyridin-6(3H)-ones and Their Fluorescence Properties
Vol 51
*
*
Xue-Cheng Liu, Wei Lin, Hui-Yan Wang, Zhi-Bin Huang, and Da-Qing Shi
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials
Science, Soochow University, Suzhou 215123, People’s Republic of China
*
E-mail: zbhuang@suda.edu.cn; dqshi@suda.edu.cn
Received April 25, 2013; Revised: 12 July 2013; Accepted: 4 August 2013
DOI 10.1002/jhet.2104
Published online 16 November 2013 in Wiley Online Library (wileyonlinelibrary.com).
A series of chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one derivatives was easily and efficiently
synthesized by the reaction of 2H-chromen-2-ones with pyrazol-5-amines catalyzed by CuCl2Á2H2O in
ethanol. This protocol has the advantages of mild reaction conditions, easy work-up, and high yields. These
compounds were showed to have high fluorescence quantum yields, which mentioned their value as
luminescence or fluorescence probe.
J. Heterocyclic Chem., 51, 1036 (2014).
INTRODUCTION
methodologies for the preparation of heterocyclic com-
pounds,[20] herein, we reported the improved and efficient
synthesis of chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-
one derivatives by the reaction of 2H-chromen-2-ones with
pyrazol-5-amines catalyzed by CuCl2Á2H2O in ethanol.
Pyrazoles, one of the most valuable N-heterocyclic com-
pounds, form an integral part of many natural products of ther-
apeutic importance and possess potentially reactive sites for a
variety of chemical reactions to generate molecular diversity.
Pyrazole derivatives have a long history of application in the
pharmaceutical industry [1] as part of biologically active phar-
maceuticals [2]. The activities exhibited by them include,
antitubercular [3], antitumor [4], anti-inflammatory [5],
antihyperglycemic [6], antimalarial [7], and platelet anti-
aggregating [8] activities.
Coumarin is one of the important parent compounds found
in many plants and could be used as the important compo-
nent of various functional materials. It is well known for its
pharmacological [9], antitumor [10], anti-inflammatory
[11], anti-coagulant [12], and anti-oxidant [13] activities.
Coumarin derivatives have a high fluorescent quantum yield
[14] and have been widely used as laser dyes, fluorescent
probes, solar energy collector, and nonlinear optical dyes
[15]. Many important compounds containing coumarin
and pyridine skeleton have been reported as potential
anti-allergic agents [16] and endothelin receptor antago-
nists [17]. The tetrahydropyridines have been identified as
potential antidepressants [18].Therefore, the synthesis of
these compounds has become of interest to synthetic chem-
ists and biologists. Although two groups [19] have reported
the synthesis of chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6
(3H)-one derivatives, both the methods gave low yields
and time-consumption. Therefore, development and intro-
duction of a convenient, efficient method for the synthesis
of chromeno[4,3-d]pyrazolo[3,4-b] pyridin-6(3H)-ones is
of practical importance and is still in demand. As a part of
our research program, which aims to develop new
RESULTS AND DISCUSSION
We initially evaluated the reaction of a 1:1 mixture of
3-acetyl-2H-chromen-2-one 1a and 3-methyl-1-phenyl-1H-
pyrazol-5-amine 2a under a variety of different conditions.
A variety of catalyst such as p-TSA, piperidine, CuSO4 · 5
H2O, CuSO4, CuCl2Á2H2O, Cu(OAc)2ÁH2O, CuI, and FeCl3
was screened. The results were summarized in Table 1.
When the reaction was carried out in ethanol without any
catalyst, the yield of product was low (entry 1, Table 1).
Basic catalyst such as piperidine resulted in poor yield
(entry 2, Table 1). Acidic catalysts, such as p-TSA, improved
the yield slightly (entry 3, Table 1). Pleasingly, when the
reaction was carried out in the presence of CuSO4Á5H2O,
CuSO4, CuCl2Á2H2O, Cu(OAc)2ÁH2O, CuI, and FeCl3 in
ethanol, the target compound 3a was obtained in 74–96%
yield (entries 4–9, Table 1). On the basis of the yield
and the reaction time, CuCl2Á2H2O was chosen as the
catalyst for all further reactions. Ethanol provided higher
yields than other organic solvents (acetonitrile, DMF,
toluene, dioxane, acetic acid, and THF) (compare entry 6
with entries 10–14), so ethanol was used as the solvent for
all further reactions.
We decided to find out the optimal amount of catalyst
(CuCl2Á2H2O) to reach complete conversion in ethanol
(entries 6, 15–17, Table 1). It was found that 10mol%
CuCl2Á2H2O was effective to catalyze this reaction (entry
© 2013 HeteroCorporation

July 2014
Improved and Efficient Synthesis of Chromeno[4,3-d]pyrazolo [3,4-b]pyridin-6(3H)-
1037
ones and Their Fluorescence Properties
Table 1
Optimizing the reaction conditions for the synthesis of 3a.
Entry
1
Catalyst (mol %)
No catalyst
Solvent
EtOH
t (°C)
Time (h)
10
Yielda (%)
32
Reflux
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
Piperidine (10)
p-TSA (10)
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
CH3CN
DMF
toluene
AcOH
THF
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
120
6
11
2.5
3
2
6
7.5
5
3.5
1.5
7
Trace
63
94
96
96
88
74
88
94
86
91
64
73
91
96
91
94
93
94
CuSO4Á5H2O (10)
CuSO4 (10)
CuCl2Á2H2O (10)
Cu(OAc)2ÁH2O (10)
CuI (10)
FeCl3 (10)
CuCl2Á2H2O (10)
CuCl2Á2H2O (10)
CuCl2Á2H2O (10)
CuCl2Á2H2O (10)
CuCl2Á2H2O (10)
CuCl2Á2H2O (5)
CuCl2Á2H2O (15)
CuCl2Á2H2O (20)
CuCl2Á2H2O (10)
CuCl2Á2H2O (10)
CuCl2Á2H2O (10)
Reflux
110
3
Reflux
Reflux
Reflux
Reflux
20
13
2.5
2
2
4
40
60
2.5
2.5
aYield was determined by HPLC-MS.
6, Table 1). From the results, 10mol% of catalyst was chosen
for further experiments.
and 3r, Table 2). When coumarin 1 had poor solubility and
R1 were electron-donating groups, the reaction would have
lower yields and longer time (3d and 3g). While R1 substit-
uents were electron-withdrawing groups, the reaction
would have higher yields and less time (entries 3b–3c,
Table 2). The effect of R2 substituents were showed in sol-
ubility and hindered reaction. n-Propyl substituent could
improve the solubility, but because of its hindered reaction,
the reactions would have lower yields and take longer time.
Because the phenyl substituent can reduce the solubility
and increase steric hindrance, the reactions would have
lower yields and take longer time (entries 3x, and 3y,
Table 2). The effect of R3 substituents were related to R1
substituents. When R1 substituents were electron-donating
groups and R3 were phenyl substituent, the reaction would
have higher yields and take less time (entry 3l, Table 2).
While R1 substituents were electron-withdrawing groups,
and R3 were phenyl substituent, the reactions would have
lower yields and take longer time (entries 3j and 3k,
Table 2). The effect of R4 substituents showed electronic
effect and steric hindrance. Phenyl substituent was an
To identify the optimum reaction temperature, the reac-
tion was carried out with 10 mol% CuCl2Á2H2O at 20°C,
at 40°C, at 60°C, and at reflux temperature; 3a was
obtained in yields of 94%, 93%, 94%, and 96% (entries
18–20 and 6, Table 1), respectively. These experiments
revealed that refluxing ethanol using 10 mol% CuCl2 · 2H2O
as catalyst provided the highest yield.
Under the optimized conditions for this CuCl2Á2H2O-
catalyzed process, we have explored the substrate scope
(Table 2). The catalytic cyclization procedure displayed
good functional group tolerance and gave the chromeno
[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-ones in good to ex-
cellent yields. The electronic effect of R1 substituents and
the solubility of coumarin 1 in ethanol had effect on the
yield of the product. When coumarin 1 had good solubility,
and R1 substituents were electron-withdrawing groups, the
reaction would have higher yields and less time (3p, 3q,
and 3s). While R1 were electron-donating groups, the reac-
tion would have lower yields and longer time (entries 3m,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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X.-C. Liu, W. Lin, H.-Y. Wang, Z.-B. Huang, and D.-Q. Shi
Vol 51
Table 2
Synthesis of chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-ones 3.
Product
R1
R2
CH3
CH3
CH3
CH3
CH3
CH3
CH3
R3
R4
Time (h)
Yielda (%)
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
3p
3q
3r
3s
H
6-Cl
6-Br
Ph
Ph
Ph
Ph
Ph
Ph
Ph
CH3
Ph
Ph
Ph
Ph
Ph
CH3
CH3
CH3
CH3
CH3
CH3
CH3
Ph
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
Ph
2
8.5
9.5
12
11
15
24
8
3.5
13
13
10
19.5
7
5.5
3
9
13
3
14
15
15
10
10
16.5
96
88
84
82
85
84
38
67
92
83
83
88
82
83
85
94
93
82
91
72
70
81
69
63
85
8-CH3O
7-CH3O
6-CH3O
7-(C2H5)2N
H
CH3
H
6-Cl
6-Br
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
n-propyl
Ph
8-CH3O
7-CH3O
6.8-Cl2
H
Ph
CH3
CH3
CH3
CH3
CH3
Ph
Ph
Ph
CH3
Ph
CH3
6-Cl
6-Br
8-CH3O
6-Cl2
H
3t
3u
3v
3w
3x
3y
6-Cl
6-Br
6-Br
H
Ph
Ph
Ph
CH3
CH3
H
Ph
aYield was isolated yield.
electron-withdrawing group, which would reduce the activity
of compound 2 and had great steric hindrance. So, the reac-
tions would have lower yields and take longer time (entries
3t–3w, Table 2).
The luminescence properties of products were shown in
Figure 1 and Table 3. It is clear that: (1) Compared with the
fluorescence date of 9,10-diphenylanthracene, the λmax(em)
of all products showed red shift. It showed that all products
were excited more easily than 9,10-diphenylanthracene,
and the emission wavelength of products appeared in the
visible light range (434.4–498.5 nm), which mentioned
their value as luminescence or fluorescence probe. (2)
The electro and steric effect of substituted group on keto-
coumarin and pyrazoles have irregular influence on the
fluorescence properties, which clearly showed that the lumi-
nescence of products depended on their resonant skeleton
and plane rigidity. (3) 3e, 3g, 3h, 3m, 3p, and 3t exhibited
Figure 1. Fluorescent emission spectra of some products
(c = 5 × 10À5 mol × LÀ1) in THF. [Color figure can be viewed in the online
issue, which is available at wileyonlinelibrary.com.]
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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Improved and Efficient Synthesis of Chromeno[4,3-d]pyrazolo [3,4-b]pyridin-6(3H)-
1039
ones and Their Fluorescence Properties
Table 3
The luminescence and fluorescence quantum yields of products 3a in THF.
Purityb (%)
Emax(abs) (MÀ1 × cmÀ1
)
λmax(ex) (nm)
λmax(em) (nm)
RFIc
ΦF
d
Comp.
9,10-diphenyl anthracene
1.9798
2.4048
2.4941
2.5323
2.5382
2.4824
2.6263
2.5468
2.4534
2.4294
2.5332
2.5290
2.5229
2.5419
2.5197
2.3147
2.4406
2.4435
2.4469
2.4318
2.5502
2.5864
2.5714
2.4635
2.3045
2.3677
220.50
221.00
220.00
221.00
220.50
219.00
220.00
220.00
220.50
220.00
222.00
221.00
220.50
219.00
221.00
219.50
220.50
220.50
220.50
220.50
221.00
220.50
221.00
223.00
219.00
219.50
428.4
459.6
479.4
478.8
462.6
449.4
464.4
456.6
462.0
444.6
467.4
469.2
461.4
457.8
498.6
435.6
439.2
441.0
496.8
459.0
471.6
487.8
489.6
471.6
438.6
435.6
5585
1919
1121
1027
362.5
4537
242.3
9123
5504
2367
1634
1351
372.2
4937
531.6
3713
6040
4178
548.2
3953
4193
3620
2978
4095
1015
1443
0.660
0.275
0.167
0.155
0.055
0.672
0.038
1.387
0.806
0.343
0.247
0.204
0.056
0.749
0.080
0.513
0.880
0.609
0.080
0.574
0.638
0.559
0.457
0.602
0.140
0.204
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
3p
3q
3r
3s
98.87
98.76
98.43
98.54
98.42
97.35
98.95
97.67
98.79
97.68
97.77
98.13
98.48
97.89
98.34
98.66
98.74
97.49
98.92
98.65
98.76
98.68
97.89
97.44
98.63
3t
3u
3v
3w
3x
3y
ac = 5 × 10-5 mol∙L-1.
bThe purity of resulting products gained by recrystallization was measured by HPLC.
cRelative fluorescence intensity.
dRelative fluorescence quantum yield.
stronger fluorescence in THF with the higher fluorescence
quantum yield than that of 9,10-diphenylanthracene
(ФF = 0.660), which showed their potential application as
new fluorescent probe or luminescence material. The UV ab-
sorption spectra of all of the compounds were recorded in
THF at 25°C, using 500 ppm solution (Fig. 2). The results
showed that the compounds do not differ much with respect
to UV absorption.
(3H)-one derivatives catalyzed by CuCl2Á2H2O in ethanol.
This method has advantage of the material easily available,
relatively mild reaction conditions, operational simplicity,
cleaner reaction profiles, and high yields. Results show that
the compounds exhibited high fluorescence quantum yields,
Furthermore, the fluorescence spectra of compounds 3e,
3m, 3q, and 3w were investigated in different solvents
(Fig. 3). The result showed that the electro and steric
effects of substituted group on keto-coumarin have differ-
ent influence on the fluorescence properties from polar
solvents to non-polar solvents.
The structures of the products were identified from their
IR, 1H-NMR, 13C-NMR, and HRMS spectra. The structures
of compounds 3a and 3w were further confirmed by X-ray
analysis (Fig. 4). The crystallographic data of these com-
pounds are summarized in Table 4.
CONCLUSIONS
Figure 2. The UV–vis absorption spectra of some products. [Color
figure can be viewed in the online issue, which is available at
wileyonlinelibrary.com.]
In summary, we developed a convenient method for
preparation of chromeno[4,3-d]pyrazolo [3,4-b]pyridin-6
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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X.-C. Liu, W. Lin, H.-Y. Wang, Z.-B. Huang, and D.-Q. Shi
Vol 51
Figure 4. X-ray crystal structure of 3a and 3w.
standard TMS. HRMS for all the compounds were determined
on Bruker MicroTOF-QII mass spectrometer with ESI resource.
Absorption and fluorescence spectra of all compounds were
obtained in a Hitachi U-3010 absorption spectrometer and a
Hitachi F-4500 fluorescence spectrometer at 25°C. X-Ray
diffraction analysis was recorded on a Rigaku Mercury CCD/AFC
diffractometer (Rigaku Corporation, Tokyo, Japan).
and this simple experimental procedure offers an alternative
route to synthesis of biologically active compounds.
EXPERIMENTAL
General.
All reagents were obtained from commercial
General procedure for the synthesis of chromeno[4,3-d]
sources and were used without further purification. IR spectra
pyrazolo[3,4-b]pyridin-6(3H)-ones.
A
mixture of 2H-
were recorded on a Varian F-1000 spectrometer (Varian Inc.,
1
Palo Alto, CA) in KBr with absorptions in cmÀ1. H-NMR (400
chromen-2-ones 1 (1 mmol), pyrazol-5-amines 2 (1 mmol), and
CuCl2Á2H2O (0.10 mmol) in ethanol (20 mL) was stirred at 80°
C for 2–24 h. After completion of the reaction confirmed by
TLC (eluent acetone/petroleum ether, V/V = 1:4), the reaction
mixture was concentrated in vacuo to remove the solvent. The
or 300 MHz) and 13C-NMR (100 or 75 MHz) spectra were
recorded on a Varian Inova-300 MHz and Varian Inova-
400 MHz in CDCl3 solution. J values are in hertz. Chemical
shifts are expressed in parts per million downfield from internal
Figure 3. The fluorescence spectra of compoundsa 3e, 3m, 3q and 3w in different solvents. [Color figure can be viewed in the online issue, which is
available at wileyonlinelibrary.com.]
Journal of Heterocyclic Chemistry
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Improved and Efficient Synthesis of Chromeno[4,3-d]pyrazolo [3,4-b]pyridin-6(3H)-
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ones and Their Fluorescence Properties
Table 4
Crystallographic data for compounds 3a and 3w.
3a
3w
Empirical formula
C
21H15N3O2
C23H18BrN3O2
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
a (Å)
b (Å)
c (Å)
α (°)
β (°)
341.36
296(2)
0.71073
Triclinic
P-1
448.31
293(2)
0.71073
Triclinic
P-1
9.9939(16)
9.4834(19)
9.6317(19)
12.468(3)
95.71(3)
98.91(3)
116.29(3)
990.4(3)
11.9406(18)
14.739(2)
73.220(2)
75.287(2)
76.824(2)
γ (°)
V (Å3)
1605.9(4)
Z
4
2
Dcalc. (Mg/m3)
Absorption coefficient (mmÀ1
F(000)
1.412
0.093
712
1.503
2.100
)
456
θ Range (°)
1.47–25.20
3.07–25.02
Limiting indices
Reflections collected
Independent reflections
Data/restraints/parameters
Goodness-of-fit on F2
Final R indices [I > 2σ(I)]
À11 ≤ h ≤ 11, À13 ≤ k ≤ 14, À16 ≤ l ≤ 17
À10 ≤ h ≤ 11, À11 ≤ k ≤ 11, À14 ≤ l ≤ 14
8374
5700
9499
3467
5700/0/472
0.941
3467/0/263
1.054
R1 = 0.0587
wR2 = 0.1270
R1 = 0.1344
wR2 = 0.1647
0.0326
R1 = 0.0578
wR2 = 0.1291
R1 = 0.1033
wR2 = 0.1505
0.0582
R indices (all data)
Extinction coefficient
Largest diff. peak and hole (e ÅÀ3
)
0.285 and À0.171
0.298 and À0.453
residue was then washed with water, filtered, dried, and
recrystallized from ethanol to afford the pure product.
δ (ppm) 19.4, 28.2, 108.9, 110.7, 116.5, 118.5, 119.2, 122.2,
127.0, 129.3, 131.8, 135.4, 138.6, 141.1, 142.7, 149.9, 151.6,
159.5, 163.5; HRMS calcd for C21H14BrN3O2Na [M + Na]+
442.0167, found 442.0161.
1,5-Dimethyl-3-phenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-
6(3H)-one (3a). mp 204–206°C; IR (KBr, cmÀ1): 3049, 1723,
1548, 1452, 1265, 1194, 1021, 823, 768, 694; 1H-NMR
(400MHz, CDCl3) δ (ppm) 2.87 (s, 3H, CH3), 3.10 (s, 3H, CH3),
7.30–7.39 (m, 3H, ArH), 7.50 (t, J = 6.8 Hz, 2H, ArH), 7.60
(t, J = 7.2 Hz, 1H, ArH), 8.22 (d, J = 7.2 Hz, 3H, ArH); 13C-NMR
(100MHz, CDCl3) δ (ppm) 19.3, 28.2, 109.0, 110.6, 116.7,
117.4, 121.9, 123.7, 126.7, 129.1, 129.4, 132.8, 138.7, 142.3,
142.7, 151.6, 152.7, 160.0, 163.3; HRMS calcd for
C21H15N3O2Na [M+ Na]+ 364.1062, found 364.1066.
8-Methoxy-1,5-dimethyl-3-phenylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3d).
mp 246–248°C; IR (KBr,
cmÀ1): 3097, 3007, 1716, 1556, 1473, 1277, 1089, 963, 813,
1
784, 759, 695; H-NMR (300 MHz, CDCl3) δ (ppm) 2.88 (s, 3H,
CH3), 3.12 (s, 3H, CH3), 4.00 (s, 3H, CH3), 7.16 (d, J = 5.1 Hz,
1H, ArH), 7.31–7.52 (m, 4H, ArH), 7.79 (d, J = 4.8 Hz, 1H, ArH),
8.23 (d, J = 4.2 Hz, 2H, ArH); 13C-NMR (75MHz, CDCl3) δ
(ppm) 19.3, 28.2, 56.6, 109.3, 114.5, 117.6, 120.8, 122.2, 123.4,
126.8, 129.2, 135.6, 138.8, 142.4, 142.7, 143.0, 147.9, 151.7,
159.5, 163.4; HRMS calcd for C22H17N3O3Na [M+ Na]+
394.1168, found 394.1180.
10-Chloro-1,5-dimethyl-3-phenylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3b).
mp 236–238°C; IR (KBr,
cmÀ1): 3077, 2924, 1731, 1556, 1471, 1434, 1246, 1032,
888, 828, 759, 672; 1H-NMR (300 MHz, CDCl3) δ (ppm)
2.92 (s, 3H, CH3), 3.12 (s, 3H, CH3), 7.34–7.54 (m, 5H,
ArH), 8.21–8.28 (m, 3H, ArH); 13C-NMR (100 MHz, CDCl3)
δ (ppm) 19.4, 28.2, 108.9, 110.7, 118.0, 118.9, 122.2, 127.0,
128.8, 129.2, 129.3, 132.6, 138.6, 141.1, 142.6, 151.1, 151.7,
159.6, 163.5; HRMS calcd for C21H15ClN3O2 [M + H]+
376.0854, found 376.0834.
9-Methoxy-1,5-dimethyl-3-phenylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3e).
mp 230–232°C. IR (KBr,
cmÀ1): 3068, 1739, 1543, 1470, 1281, 1047, 861, 797, 756,
1
688; H-NMR (300 MHz, CDCl3) δ (ppm) 2.90 (s, 3H, CH3),
3.11 (s, 3H, CH3), 3.93 (s, 3H, CH3), 6.89–6.97 (m, 2H,
ArH), 7.35 (t, J = 6.9 Hz, 1H, ArH), 7.53 (t, J = 5.7 Hz, 2H,
ArH), 8.18–8.25 (m, 3H, ArH); 13C-NMR (100 MHz, CDCl3)
δ (ppm) 19.4, 28.3, 56.0, 101.2, 108.7, 109.3, 109.9, 111.9,
118.3, 122.1, 126.7, 129.2, 130.5, 138.8, 142.7, 142.8, 151.7,
154.7, 160.2, 163.4; HRMS calcd for C22H17N3O3Na [M+ Na]+
394.1168, found 394.1156.
10-Bromo-1,5-dimethyl-3-phenylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3c).
mp 242–244°C; IR (KBr,
cmÀ1): 3081, 2927, 1729, 1588, 1470, 1246, 1031, 880, 749,
1
685; H-NMR (300 MHz, CDCl3) δ (ppm) 2.93 (s, 3H, CH3),
3.13 (s, 3H, CH3), 7.30–7.72 (m, 5H, ArH), 8.23 (d, J = 6.6
10-Methoxy-1,5-dimethyl-3-phenylchromeno[4,3-d]pyrazolo
Hz, 2H, ArH), 8.46 (s, 1H, ArH); 13C-NMR (75MHz, CDCl3)
[3,4-b]pyridin-6(3H)-one (3f).
mp 200–202°C; IR (KBr,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

1042
X.-C. Liu, W. Lin, H.-Y. Wang, Z.-B. Huang, and D.-Q. Shi
Vol 51
cmÀ1): 2969, 2837, 1716, 1553, 1473, 1233, 1149, 1047, 842,
813, 759, 675; H-NMR (300 MHz, CDCl3) δ (ppm) 2.96 (s, 3H,
3082, 2957, 2865, 1730, 1553, 1488, 1275, 1096, 965, 786, 753,
690; 1H-NMR (400 MHz, CDCl3) δ (ppm) 1.10 (t, J=7.2Hz,
3H, CH3), 1.89–1.94 (m, 2H, CH2), 2.88 (s, 3H, CH3), 3.53
(t, J= 7.6 Hz, 2H, CH2), 4.00 (s, 3H, CH3), 7.16 (d, J=8.0Hz,
1H, ArH), 7.30–7.35 (m, 2H, ArH), 7.53 (t, J= 7.6 Hz, 2H,
ArH), 7.79 (d, J= 8.0 Hz, 1H, ArH), 8.30 (d, J= 8.0 Hz, 2H,
ArH); 13C-NMR (75 MHz, CDCl3) δ (ppm) 14.4, 19.2, 22.0,
41.1, 56.5, 109.1, 110.4, 114.3, 117.5, 120.8, 121.8, 123.4,
126.5, 129.1, 138.9, 142.5, 142.8, 142.9, 147.7, 151.7, 159.1,
166.7; HRMS calcd for C24H22N3O3 [M + H]+ 400.1662, found
400.1656.
9-Methoxy-1-methyl-3-phenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3m). mp 194–196°C; IR (KBr, cmÀ1):
2956, 1739, 1540, 1274, 1207, 1165, 800, 756, 685; 1H-NMR
(400 MHz, CDCl3) δ (ppm) 1.10 (t, J= 7.2 Hz, 3H, CH3), 1.86–1.96
(m, 2H, CH2), 2.88 (s, 3H, CH3), 3.48 (t, J = 7.6 Hz, 2H,
CH2), 3.93 (s, 3H, CH3), 6.88–6.96 (m, 2H, ArH), 7.33
(t, J = 7.2 Hz, 1H, ArH), 7.53 (t, J = 8.0 Hz, 2H, ArH), 8.15
(d, J = 8.8 Hz, 1H, ArH), 8.30 (d, J = 7.2 Hz, 2H, ArH); 13C-
NMR (75 MHz, CDCl3): δ (ppm) 14.5, 19.3, 22.0, 41.2,
56.0, 101.0, 108.4, 108.9, 109.9, 111.8, 121.7, 126.4, 129.1,
130.5, 138.9, 142.8, 142.9, 151.7, 154.6, 159.8, 163.4,
166.8; HRMS calcd for C24H21N3O3Na [M + Na]+ 422.1481,
found 422.1481.
1
CH3), 3.12 (s, 3H, CH3), 3.94 (s, 3H, CH3), 7.19 (d, J = 6.6 Hz,
1H, ArH), 7.31–7.37 (m, 2H, ArH), 7.53 (t, J = 6.3 Hz, 2H, ArH),
7.72 (s, 1H, ArH), 8.23 (d, J = 6.9 Hz, 2H, ArH); 13C-NMR
(100MHz, CDCl3) δ (ppm) 19.7, 28.3, 56.2, 109.0, 110.9, 112.9,
117.2, 118.4, 119.7, 122.1, 126.8, 129.2, 138.7, 142.3, 142.5,
147.0, 151.6, 155.7, 160.2, 163.5; HRMS calcd for
C22H17N3O3Na [M+ Na]+ 394.1168, found 394.1170.
9-Diethylamino-1,5-dimethyl-3-phenylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3g).
mp 236–238°C (Lit. [19]
240–241°C); IR (KBr, cmÀ1): 2969, 1738, 1613, 1465, 1225,
1120, 1031, 820, 769, 682; 1H-NMR (300 MHz, CDCl3) δ
(ppm) 1.24 (s, 6H, CH3), 2.86 (s, 3H, CH3), 3.05 (s, 3H, CH3),
3.44 (s, 4H, CH2), 6.50–6.63 (m, 3H, ArH), 7.31–7.50 (m, 3H,
ArH), 8.02–8.23 (m, 3H, ArH).
3,5-Dimethyl-1-phenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-
6(3H)-one (3h). mp 238–240°C; IR (KBr, cmÀ1): 3059, 1722,
1545, 1451, 1255, 1196, 1021, 822, 768, 693; 1H-NMR
(400MHz, CDCl3) δ (ppm) 3.16 (s, 3H, CH3), 4.27 (s, 3H, CH3),
6.68 (t, J = 7.2 Hz, 1H, ArH), 7.29 (t, J = 8.4 Hz, 2H, ArH),
7.39–7.47 (m, 6H, ArH); 13C-NMR (75MHz, CDCl3) δ (ppm)
28.1, 34.4, 105.5, 110.5, 115.8, 116.7, 122.9, 128.7, 128.9,
129.6, 131.5, 132.5, 134.7, 142.2, 146.1, 152.0, 152.6, 160.3,
163.3; HRMS calcd for C21H15N3O2Na [M + Na]+ 364.1062,
found 364.1078.
8,10-Dichloro-1-methyl-3-phenyl-5-propylchromeno[4,3-d]
pyrazolo[3,4-b]pyridin-6(3H)-one (3n).
mp 190–192°C; IR
1-Methyl-3-phenyl-5-propylchromeno[4,3-d]pyrazolo[3,4-b]
(KBr, cmÀ1): 3078, 2962, 2869, 1745, 1543, 1482, 1265,
1
pyridin-6(3H)-one (3i).
mp 144–146°C; IR (KBr, cmÀ1):
1031, 848, 788, 756, 691, 666; H-NMR (400 MHz, CDCl3) δ
2956, 2873, 1729, 1593, 1555, 1471, 1231, 1162, 1047, 808,
748, 688, 673; 1H-NMR (300 MHz, CDCl3) δ (ppm) 1.12 (t,
J = 6.9 Hz, 3H, CH3), 1.61–1.98 (m, 2H, CH2), 2.89 (s, 3H,
CH3), 3.51 (t, J = 6.3 Hz, 2H, CH2), 7.34–7.65 (m, 6H, ArH),
8.23–8.31 (m, 3H, ArH); 13C-NMR (100 MHz, CDCl3) δ (ppm)
14.1, 19.2, 22.0, 41.1, 108.8, 110.3, 116.8, 117.4, 121.7, 123.7,
126.5, 129.1, 129.4, 132.7, 138.9, 142.6, 142.8, 151.7, 152.7,
159.6, 166.7; HRMS calcd for C23H19N3O2Na [M + Na]+
392.1374, found 392.1371.
(ppm) 1.10 (t, J = 7.2 Hz, 3H, CH3), 1.84–1.93 (m, 2H, CH2),
2.87 (s, 3H, CH3), 3.47 (t, J = 7.6 Hz, 2H, CH2), 7.32
(t, J = 7.2 Hz, 1H, ArH), 7.49 (t, J = 7.6 Hz, 2H, ArH), 7.64
(s, 1H, ArH), 8.12 (s, 1H, ArH), 8.23 (d, J = 7.6 Hz, 2H, ArH);
13C-NMR (75 MHz, CDCl3) δ (ppm) 14.4, 19.2, 21.9, 41.0,
108.6, 110.0, 118.8, 121.4, 123.2, 126.6, 127.3, 128.8, 129.0,
132.3, 138.5, 140.6, 142.3, 147.0, 151.4, 157.9, 166.7; HRMS
calcd for C23H17Cl2N3O2Na [M + Na]+ 460.0596, found
460.0610.
10-Chloro-1-methyl-3-phenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3j). mp 204–206°C; IR (KBr, cmÀ1):
2956, 1739, 1595, 1543, 1483, 1198, 1028, 836, 749, 688;
1H-NMR (300 MHz, CDCl3) δ (ppm) 1.10 (t, J = 7.2 Hz, 3H,
CH3), 1.83–1.97 (m, 2H, CH2), 2.90 (s, 3H, CH3), 3.49
(t, J = 6.4 Hz, 2H, CH2), 7.33–7.54 (m, 5H, ArH), 8.25–8.27
(m, 3H, ArH); 13C-NMR (100 MHz, CDCl3) δ (ppm) 14.4,
19.3, 22.0, 41.1, 108.6, 110.3, 118.0, 118.8, 121.8, 126.7,
128.8, 129.2, 132.5, 138.7, 141.2, 142.5, 151.0, 151.6,
159.1, 166.8; HRMS calcd for C23H18ClN3O2Na [M + Na]+
429.0986, found 429.0978.
1,3-Dimethyl-5-propylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-
6(3H)-one (3o). mp 130–132°C; IR (KBr, cmÀ1): 2959, 2933,
2872, 1722, 1562, 1459, 1267, 1232, 1178, 1011, 806, 764, 681,
659; 1H-NMR (300 MHz, CDCl3) δ (ppm) 1.10 (t, J = 6.3 Hz, 3H,
CH3), 1.79–1.95 (m, 2H, CH2), 2.84 (s, 3H, CH3), 3.48
(t, J = 6.0 Hz, 2H, CH2), 4.14 (s, 3H, CH3), 7.40–7.61 (m, 3H,
ArH), 8.27 (d, J = 7.8 Hz, 1H, ArH); 13C-NMR (75 MHz, CDCl3)
δ (ppm) 14.5, 19.2, 22.4, 33.8, 41.2, 107.0, 109.5, 117.0, 117.3,
123.6, 129.3, 132.6, 141.2, 142.8, 152.1, 152.7, 159.9, 166.4;
HRMS calcd for C18H17N3O2Na [M + Na]+ 330.1219, found
330.1221.
10-Bromo-1-methyl-3-phenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3k). mp 206–208°C; IR (KBr, cmÀ1):
2953, 2862, 1740, 1546, 1507, 1482, 1253, 1189, 1022, 835, 757,
10-Chloro-1,3-dimethyl-5-propylchromeno[4,3-d]pyrazolo[3,4-b]
pyridin-6(3H)-one (3p). mp 180–182°C; IR (KBr, cmÀ1): 2958,
2870, 1728, 1560, 1419, 1256, 1181, 1050, 839, 802, 754, 669,
1
1
684; H-NMR (300 MHz, CDCl3) δ (ppm) 1.10 (t, J= 6.6 Hz, 3H,
654; H-NMR (300 MHz, CDCl3) δ (ppm) 1.10 (t, J= 7.2 Hz, 3H,
CH3), 1.84–1.97 (m, 2H, CH2), 2.91 (s, 3H, CH3), 3.50 (t,
J= 6.9 Hz, 2H, CH2), 7.29–7.34 (m, 2H, ArH), 7.53 (t, J=7.5Hz,
2H, ArH), 7.69 (d, J= 8.4 Hz, 1H, ArH), 8.27 (d, J= 7.5 Hz, ArH),
8.41 (s, 1H, ArH); 13C-NMR (100 MHz, CDCl3) δ (ppm) 14.4,
19.3, 21.9, 41.1, 108.5, 110.2, 116.3, 118.4, 119.0, 121.5, 126.6,
129.1, 131.7, 135.2, 138.7, 141.0, 142.5, 151.4, 151.5, 158.9,
166.6; HRMS calcd for C23H18BrN3O2Na [M + Na]+ 470.0480,
found 470.0460.
CH3), 1.76–1.89 (m, 2H, CH2), 2.86 (s, 3H, CH3), 3.46
(t, J= 7.5 Hz, 2H, CH2), 4.14 (s, 3H, CH3), 7.35 (d, J=8.7Hz, 1H,
ArH), 7.55 (d, J= 8.4 Hz, 1H, ArH), 8.28 (s, 1H, ArH); 13C-NMR
(100 MHz, CDCl3) δ (ppm) 14.4, 19.3, 22.3, 33.9, 41.2, 106.8,
109.4, 118.2, 118.7, 128.6, 129.1, 132.3, 140.9, 141.3, 151.0, 152.1,
159.3, 166.3; HRMS calcd for C18H16ClN3O2Na [M + Na]+
364.0829, found 364.0848.
10-Bromo-1,3-dimethyl-5-propylchromeno[4,3-d]pyrazolo[3,4-b]
pyridin-6(3H)-one (3q). mp 184–186°C; IR (KBr, cmÀ1): 2959,
2863, 1719, 1562, 1472, 1270, 1174, 1033, 828, 748, 697, 652; 1H-
8-Methoxy-1-methyl-3-phenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3l). mp 216–218°C. IR (KBr, cmÀ1):
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

July 2014
Improved and Efficient Synthesis of Chromeno[4,3-d]pyrazolo [3,4-b]pyridin-6(3H)-
1043
ones and Their Fluorescence Properties
NMR (300 MHz, CDCl3) δ (ppm) 1.10 (t, J= 7.2 Hz, 3H, CH3), 1.78–
1.91 (m, 2H, CH2), 2.83 (s, 3H, CH3), 3.43 (t, J= 7.8 Hz, 2H, CH2),
4.13 (s, 3H, CH3), 7.27 (d, J= 7.5 Hz, 1H, ArH), 7.66 (d, J=6.6Hz,
1H, ArH), 8.40 (s, 1H, ArH); 13C-NMR (75 MHz, CDCl3) δ (ppm)
14.4, 19.3, 22.3, 33.9, 41.2, 106.7, 109.3, 116.2, 118.6, 118.9,
131.5, 135.1, 141.0, 141.2, 151.4, 152.0, 159.1, 166.3; HRMS calcd
for C18H16BrN3O2Na [M + Na]+ 408.0324, found 408.0316.
159.1, 167.2; HRMS calcd for C28H20BrN3O2Na [M+ Na]+
532.0637, found 532.0614.
10-Bromo-3-methyl-1-phenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3w). mp 194–196°C. IR (KBr, cmÀ1):
1
2948, 1729, 1548, 1438, 1258, 1018, 924, 820, 694. H-NMR
(400 MHz, CDCl3) δ (ppm) 1.12 (t, J = 7.2 Hz, 3H, CH3),
1.86–1.95 (m, 2H, CH2), 3.52 (t, J = 7.6 Hz, 2H, CH2), 4.28
(s, 3H, CH3), 7.18 (d, J = 8.8 Hz, 1H, ArH), 7.42–7.53 (m,
7H, ArH); 13C-NMR (75 MHz, CDCl3) δ (ppm) 14.5, 22.4,
34.3, 41.2, 105.1, 110.0, 115.8, 117.4, 118.1, 128.9, 129.3,
129.4, 134.2, 134.3, 135.1, 140.9, 145.9, 151.3, 152.0,
159.2, 166.7; HRMS calcd for C23H18BrN3O2Na [M + Na]+
470.0480, found 470.0475.
1-Methyl-3,5-diphenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-
6(3H)-one (3x). mp 230–232°C; IR (KBr, cmÀ1): 3076, 3055,
2964, 1727, 1544, 1505, 1469, 1245, 1205, 1148, 1049, 984, 814,
757, 689; 1H-NMR (300 MHz, CDCl3) δ (ppm) 2.93 (s, 3H,
CH3), 7.31–7.66 (m, 11H, ArH), 8.25–8.30 (m, 3H, ArH); 13C-
NMR (100MHz, CDCl3) δ (ppm) 19.1, 109.4, 109.5, 116.8,
117.7, 122.0, 123.9, 126.8, 128.11, 129.2, 129.4, 129.5, 133.0,
138.7, 141.2, 143.0, 143.2, 151.6, 152.8, 159.1, 163.1; HRMS
calcd for C26H17N3O2Na [M+ Na]+ 426.1219, found 426.1195.
1,3-Dimethyl-5-phenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-
6(3H)-one (3y). mp 188–190°C; IR (KBr, cmÀ1): 2987, 1735,
1556, 1460, 1259, 1172, 1050, 780, 761, 674; 1H-NMR
(300 MHz, CDCl3) δ (ppm) 2.90 (s, 3H, CH3), 4.17 (s, 3H, CH3),
7.49–7.63 (m, 8H, ArH), 8.33 (s, 1H, ArH); 13C-NMR (75MHz,
CDCl3) δ (ppm) 19.1, 34.1, 107.6, 108.8, 117.0, 117.6, 123.9,
128.1, 129.0, 129.3, 132.8, 141.5, 143.2, 152.1, 152.8, 159.3,
162.8; HRMS calcd for C21H17N3O2Na [M+ Na]+ 364.1062,
found 364.1058.
8-Methoxy-1,3-dimethyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3r).
mp 188–190°C; IR (KBr,
cmÀ1): 3089, 2950, 2867, 1719, 1562, 1487, 1279, 1091, 973,
811, 787, 681; 1H-NMR (400 MHz, CDCl3) δ (ppm) 1.10
(t, J = 7.2Hz, 3H, CH3), 1.81–1.91 (m, 2H, CH2), 2.81 (s, 3H,
CH3), 3.45 (t, J = 7.6 Hz, 2H, CH2), 4.00 (s, 3H, CH3), 4.13
(s, 3H, CH3), 7.15 (d, J = 8.0 Hz, 1H, ArH), 7.29 (t, J = 8.0 Hz,
1H, ArH), 7.79 (d, J = 8.0 Hz, 1H, ArH); 13C-NMR (75 MHz,
CDCl3) δ (ppm) 14.4, 19.1, 22.3, 33.8, 41.1, 56.4, 107.2, 109.4,
114.1, 117.6, 120.6, 123.2, 141.3, 142.4, 142.9, 147.6, 152.0,
159.3, 166.3; HRMS calcd for C19H19N3O3Na [M + Na]+
360.1324, found 360.1316.
8,10-Dichloro-1,3-dimethyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3s). mp 176–178°C; IR (KBr, cmÀ1):
3072, 2964, 2861, 1737, 1551, 1446, 1260, 1157, 1027, 871,
808, 781, 758; 1H-NMR (400 MHz, CDCl3) δ (ppm) 1.10
(t, J = 7.2 Hz, 3H, CH3), 1.79–1.88 (m, 2H, CH2), 2.82 (s, 3H,
CH3), 3.44 (t, J = 7.6 Hz, 2H, CH2), 4.13 (s, 3H, CH3), 7.64
(s, 1H, ArH), 8.16 (s, 1H, ArH); 13C-NMR (100 MHz, CDCl3)
δ (ppm) 14.4, 19.2, 22.3, 34.0, 41.1, 106.9, 109.3, 119.2,
123.2, 127.1, 128.7, 132.2, 137.0, 140.9, 147.1, 152.1, 158.2,
166.4; HRMS calcd for C18H15Cl2N3O2Na [M + Na]+
398.0439, found 398.0423.
1,3-Diphenyl-5-propylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-
6(3H)-one (3t). mp 222–224°C; IR (KBr, cmÀ1): 2936, 1728,
1603, 1542, 1261, 1049, 845, 758, 687; 1H-NMR (400 MHz,
CDCl3) δ (ppm) 1.14 (t, J = 7.3 Hz, 3H, CH3), 1.92–2.02 (m, 2H,
CH2), 3.59 (t, J = 7.6 Hz, 2H, CH2), 6.70 (t, J = 7.6Hz, 1H, ArH),
7.31–7.59 (m, 11H, ArH), 8.40 (d, J = 8.0 Hz, 2H, ArH);
13C-NMR (75 MHz, CDCl3) δ (ppm) 14.5, 22.1, 41.2, 107.0,
110.9, 115.8, 116.7, 122.2, 122.9, 126.9, 128.8, 129.2, 129.7,
131.6, 132.6, 134.4, 139.0, 142.4, 147.3, 151.8, 152.6, 159.7,
167.2; HRMS calcd for C28H21N3O2Na [M + Na]+ 454.1532,
found 454.1538.
Acknowledgments. We are grateful for financial support from
the Major Basic Research Project of the Natural Science
Foundation of the Jiangsu Higher Education Institutions (No.
10KJA150049), the Natural Science Foundation of the Jiangsu
Higher Education Institutions (No. 11KJB150014), a project
fund from the Priority Academic Project Development of the
Jiangsu Higher Education Institutions, the Foundation of the
Key Laboratory of Organic Synthesis of the Jiangsu Province
(No. JSK1210), and the Jiangsu College Graduate Research and
Innovation Project of the Jiangsu Province Department of
Education (CXZZ11_0090).
10-Chloro-1,3-diphenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3u).
mp 228–230°C; IR (KBr,
cmÀ1): 2953, 1747, 1644, 1543, 1421, 1261, 1157, 819, 679;
1H-NMR (400 MHz, CDCl3) δ (ppm) 1.14 (t, J = 7.6 Hz, 3H,
CH3), 1.92–2.01 (m, 2H, CH2), 3.57 (t, J = 7.6 Hz, 2H, CH2),
7.26–7.58 (m, 11H, ArH), 8.38–8.40 (m, 2H, ArH); 13C-NMR
(75 MHz, CDCl3) δ (ppm) 14.5, 22.1, 41.2, 106.9, 110.9, 116.9,
117.9, 122.2, 127.0, 128.6, 129.0, 129.2, 129.5, 129.7, 131.4,
132.4, 134.1, 138.9, 141.0, 147.1, 150.9, 151.7, 159.2, 167.2;
HRMS calcd for C28H20ClN3O2Na [M + Na]+ 488.1142, found
488.1165.
REFERENCES AND NOTES
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Nogueras, M.; Cobo, J. Eur J Med Chem 2011, 46, 2436; (b) Carboni, J.
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10-Bromo-1,3-diphenyl-5-propylchromeno[4,3-d]pyrazolo
[3,4-b]pyridin-6(3H)-one (3v).
mp 240–242°C; IR (KBr,
cmÀ1): 3059, 1742, 1540, 1419, 1262, 1161, 1025, 836, 757,
1
690; H-NMR (400 MHz, CDCl3) δ (ppm) 1.14 (t, J = 7.2 Hz,
3H, CH3), 1.92–2.01 (m, 2H, CH2), 3.58 (t, J = 7.2 Hz, 2H,
CH2), 7.22 (d, J = 8.0 Hz, 1H, ArH), 7.39 (t, J = 7.2 Hz, 1H,
ArH), 7.49–7.59 (m, 9H, ArH), 8.39 (d, J = 7.6 Hz, 2H, ArH);
13C-NMR (75 MHz, CDCl3) δ (ppm) 14.5, 22.1, 41.2, 106.9,
110.9, 115.9, 117.3, 118.2, 122.3, 127.11, 129.1, 129.2, 129.5,
129.8, 134.0, 134.4, 135.3, 138.9, 141.0, 147.2, 151.4, 151.7,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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X.-C. Liu, W. Lin, H.-Y. Wang, Z.-B. Huang, and D.-Q. Shi
Vol 51
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet