Synthesis of 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine- 1,8-dione derivatives

Article abstract of DOI:10.1002/jhet.764

A series of novel 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8- dione derivatives 4 were synthesized by hydrazine or phenylhydrazine and 9-aryl-1,8-dioxo-2,3,4,5,6,7,9-heptahydroxanthene derivatives 3, which were prepared by 5-substituted-1,3-cyclohexanedione 1 and aromatic aldehydes 2 in the presence of concentrated H₂SO₄ as a catalyst in water. The structures of all compounds were characterized by IR, MS, ¹H-NMR, and elemental analysis, and the title compounds possess good fluorescence properties..

Full text of DOI:10.1002/jhet.764

January 2012
Synthesis of 10-Amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-
1,8-dione Derivatives
195
Guang-Fan Han,* Bin Cui, Li-Zhuang Chen, and Xiao-Lei Hu
School of Material Science and Engineering, Jiangsu University of Science and Technology,
Zhenjiang, Jiangsu 212003, China
*E-mail: gf552002@yahoo.com.cn
Received September 8, 2010
DOI 10.1002/jhet.764
Published online 24 August 2011 in Wiley Online Library (wileyonlinelibrary.com).
A series of novel 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione derivatives 4 were
synthesized by hydrazine or phenylhydrazine and 9-aryl-1,8-dioxo-2,3,4,5,6,7,9-heptahydroxanthene
derivatives 3, which were prepared by 5-substituted-1,3-cyclohexanedione 1 and aromatic aldehydes 2
in the presence of concentrated H2SO4 as a catalyst in water. The structures of all compounds were
1
characterized by IR, MS, H-NMR, and elemental analysis, and the title compounds possess good fluo-
rescence properties.
J. Heterocyclic Chem., 49, 195 (2012).
INTRODUCTION
as chemiluminescent DNA probes, DNA, and other
macromolecules embedded in body [6–8]. This class of
compounds belongs to several agents of clinical impor-
tance such as actinomycin-D, daunomycin, adriamycin,
tacine, and amsacrine [9,10].
The family of acridine derivatives is a class of the
earliest discovered bioactive compounds, which were
widely used as antibacterial, anti-inflammatory, antima-
larial, deworming, antitumor, anti-blood-sucking insects,
and memory enhancement agents [1–3]. The emergence
of penicillin eclipsed acridines in antisepsis because of
the greater therapeutic efficiency compared with the for-
mer. However, with current rapid increasement in drug-
resistant bacterial infection, novel acridine derivatives
may be of new use. A great many researches and devel-
opments have been carried out on acridine derivatives
[4,5]. In these areas, recent study has been focused
mainly on their functions as anticancer drugs, because
of their ability of the acridine chromophore to interca-
late DNA and inhibit topoisomerase enzyme, which fur-
ther block the action of DNA-metabolizing proteins
pharmacologically. At the same time, as acridine has
large ring-conjugated system and a rigid planar struc-
ture, it is a good fluorescent reagent, which can be used
In terms of considerable synthetic attention being paid
to the substituted aminoacridines, the mode of binding of
acridine molecules involves intercalation of the acridine
ring between adjacent base pairs in the DNA duplex and
acridines moieties are held in place by van der Waals
force supplemented by stronger ionic bonds to the phos-
phate ions of the DNA backbone [11–13]. Here, we
reported the synthesis of the title compounds in this study.
We hope that these novel acridine derivatives will be of
anticancer activities and fluorescence probes.
RESULTS AND DISCUSSION
The synthetic route is shown in Scheme 1; melting
point and yields of the title compounds are given in
C
V
2011 HeteroCorporation

196
G.-F. Han, B. Cui, L.-Z. Chen, and X.-L. Hu
Vol 49
Scheme 1
Table 1. Most importantly, aromatic aldehydes with
either electron-donating or electron-withdrawing substitu-
ents reacted very well to afford the corresponding hepta-
hydroxanthene derivatives 3, and the title compounds
were obtained with good yields and high purity.
3c by a conjugated addition reaction started from the
nitrogen atom of enamine attacks toward the C¼¼C of
ketene-conjugated system in another six-membered ring.
The further dehydration reaction constructs a wide-area
conjugated system through the three cycles of the gener-
ated inner-salt-like intermediate 3d, which finally rear-
ranges to the title compound 4.
A plausible formation mechanism of 4 from 3 is
shown in Scheme 2. The oxygen atom in pyran ring
exhibits stronger electron-withdrawing effect due to its
attaching to a cyclic ketene moiety and promotes the
Michael addition reaction of hydrazine with another
cyclohexenone structure in the asymmetrical position.
The electron transfer of negative ion of enol 3a, as an
initial intermediate in the nucleophilic addition reaction,
results in ring opening to form an open-chain molecule
3b, which is anew cyclized into a tricyclic intermediate
The structures of the prepared 10-amino-9-aryl-
2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione 4a–o were
1
fully characterized by H-NMR, MS, IR, and elemental
1
analysis. For example, in the H-NMR of 4a, the two
single proton peaks at d 0.96 and 1.12 ppm were attrib-
uted to the protons of four gem-methyl groups at 3- and
6-position. The two groups of deformation doublets at
2.13–2.26 ppm, showed
a large mutual coupling
Table 1
Synthesis of 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione derivatives.
Entry
R
R1
R2
R3
m.p.a (ꢀC)
Yieldb (%)
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
3-NO2
4-Cl
CH3
CH3
CH3
CH3
CH3
CH3
CH3
H
H
H
224–226
274–276
260–262
204–206
212–214
244–246
188–190
212–214
220–222
236–238
176–178
69
68
71
63
65
58
65
61
71
82
80
76
83
74
50
H
2-Cl
CH3
CH3
H
H
3,4-(OCH3)2
H
4-Cl
3-NO2
3,4-(OCH3)2
H
2-Cl
4-Cl
3-NO2
2-Cl
3,4-(OCH3)2
CH3
C6H5
H
H
C6H5
C6H5
H
H
H
H
C6H5
C6H5
C6H5
H
H
H
H
C6H5
C6H5
H
4-OCH3C6H4
4-OCH3C6H4
4-OCH3C6H4
4-OCH3C6H4
H
H
>260
H
262–264
242–244
222–224
H
H
H
H
a Melting points were determined on an electrothermal apparatus, and the temperature was not calibrated.
b Yield refers to pure products after chromatography.
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January 2012 Synthesis of 10-Amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione Derivatives
197
Scheme 2
constant (J ¼ 16.20 Hz, Dm ¼ 22.02 Hz, Dm/J ¼ 1.36),
were ascribable to the proton of two methylene at 4-
and 5-position. The chemical shifts of four gem-protons
with gem-coupling constant (J ¼ 17.82 Hz, Dm ¼ 91.83
Hz, Dm/J ¼ 5.15), linked in 2- and 7-position, were
found at 2.51–2.88 ppm in the form of deformation dou-
ble peaks. With the decrease in the ratio of Dm/J, the
outside proton peak gradually became smaller and the
inside proton peak gradually became larger and closer
[14]. The similar peaks pattern of the methylene at 4-
and 5-position, and 2- and 7-position of compounds 4a–e
photoluminescent spectra of the compounds in dichloro-
methane solution are of particular interest. Fluorescence
efficiency can be correlated with many structural features
of chemicals including p–p* and n–p* transitions, struc-
tural rigidity, noncovalent interactions (e.g., hydrogen
bonds, p–p interactions, and hydrophilic and hydrophobic
interactions), interior intermolecular energy transfers, and
photoinduced electron transfers [15,16]. Only the fluores-
cence of 4e and 4g is detected. The dichloromethane solu-
tion fluorescent spectra for compound 4e at room temper-
ature reveal an emission peak at 521/496 nm (the exciting
radiation set at 367/398 nm) as shown in Figure 1. The
dichloromethane solution fluorescent spectra for com-
pound 4g at room temperature reveal an emission peak at
522/498 nm (the exciting radiation set at 357/410 nm) as
shown in Figure 2. The emission band may be attributed
to the p–p* transition of the pyridine ring [17,18].
1
was also observed in the H-NMR. The broad single pro-
ton peaks at d 4.13 ppm disappeared after D2O exchang-
ing and therefore were attributed to the characteristic
absorption proton peak of the two NAH of the amino
group. The multiple proton peaks at 7.35–7.96 ppm were
attributed to the characteristic absorption proton peak of
the four H of the benzene ring. In the IR spectra of 4a,
several typical absorption bands at 1625 cmꢁ1 for
(C¼¼O) and 3350 cmꢁ1 for (NAH) were observed. In
ESI mass spectra, the molecular ion peak m/z ¼ 401.2.
Each of compounds 4f–o should be as a diastereo-
meric mixture, so that the proton peak for the one H of
9-position displays two single peaks. It was speculated
1
from the H-NMR spectrum that the yields of the major
product were above 90%. The specific stereostructures
of the main product need to be further studied.
LUMINESCENT PROPERTIES
The xanthene derivatives 3 are converted to acridine
derivatives 4 by replacing the oxygen atoms with the
nitrogen atoms bearing amino. As the electronegativity
of nitrogen atoms is lower than that of oxygen atoms,
the nonconjugated bond of the lone pair electrons is rel-
atively easy to delocalize, so that the absorption wave-
length of acridine derivatives 4 occurs red shift, and the
Figure 1. Fluorescent excitement (left) and emission (right) spectra of
the compound 4e.
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198
G.-F. Han, B. Cui, L.-Z. Chen, and X.-L. Hu
Vol 49
was stirred at 70–80ꢀC for 2 h [19b] and then the mixture
was cooled to rt. The solid (the crude product 3) was filtered
off and washed with water. The mixture of crude product 3
and hydrazine (5 mL) or phenylhydrazine (5 mL) was stirred
at 80–90ꢀC, and the reaction mixture was cooled to rt when
the reaction was over by TLC analysis. The solid (the crude
title compounds 4) was filtered off, washed with water, and
purified with silica gel flash chromatography using ethyl ace-
tate/hexane mixture (1:2) as an eluent to give pure
compounds.
Data of compounds are shown as follows: 4a: Yield: 69%;
1H-NMR (CDCl3, 300 MHz) d: 0.96 (s, 6H, 2ꢂCH3), 1.12 (s,
6H, 2ꢂCH3), 2.13–2.26 (m, 4H, C4þC5-H), 2.51–2.88 (m, 4H,
C2þC7-H), 4.13 (br s, 2H, NAH), 5.27 (s, 1H, C9-H), 7.35–
7.96 (m, 4H, Ph-H); IR (KBr) m: 3350 (NH), 1625 (C¼¼O);
MS (70 eV) m/z (%): 410.2 (Mþ1, 100); Anal. calcd for
C23H27N3O4: C, 67.46; H, 6.65; N, 10.26. Found: C, 67.50; H,
6.71; N, 10.35.
Figure 2. Fluorescent excitement (left) and emission (right) spectra of
the compound 4g.
4b: Yield: 68%; 1H-NMR (CDCl3, 300 MHz) d: 0.96 (s,
6H, 2ꢂCH3), 1.12 (s, 6H, 2ꢂCH3), 2.14–2.25 (m, 4H, C4þC5-
H), 2.47–2.83 (m, 4H, C2þC7-H), 4.02 (br s, 2H, NAH), 5.15
(s, 1H, C9-H), 7.13–7.23 (m, 4H, Ph-H); IR (KBr) m: 3210
(NH), 1580 (C¼¼O); MS (70 eV) m/z (%): 399.2 (Mþ1, 100);
Anal. calcd for C23H27ClN2O2: C, 69.25; H, 6.82; N, 7.02.
Found: C, 69.16; H, 6.75; N, 7.10.
CONCLUSION
In summary, during the synthesis of 10-amino-9-aryl-
2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione derivatives 4,
we first prepared 9-aryl-1,8-dioxo-2,3,4,5,6,7,9-heptahy-
droxanthene derivatives 3 with H2SO4/H2O as a catalyst.
Then, the title compounds 4 were obtained by the reac-
tion of the compounds 3 with hydrazine or phenylhydra-
zine under solvent-free condition. Both the method and
the 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydro-acridine-
1,8-dione derivatives have not been reported. The xan-
thene derivatives 3 are converted to acridine derivatives
4 by replacing the oxygen atoms with the nitrogen
atoms bearing amino; the absorption wavelength of acri-
dine derivatives 4 occurs red shift, and the photolumi-
nescent spectra of the title compounds in dichlorome-
thane solution are of particular interest. Only the fluores-
cence of 4e and 4g is detected, and both of them show
good fluorescence properties.
1
4c: Yield: 71%; H-NMR (CDCl3, 300 MHz) d: 0.97 (s, 6H,
2ꢂCH3), 1.11 (s, 6H, 2ꢂCH3), 2.13–2.26 (m, 4H, C4þC5-H),
2.47–2.83 (m, 4H, C2þC7-H), 4.01 (br s, 2H, NAH), 5.20 (s,
1H, C9-H), 7.06–7.28 (m, 5H, Ph-H); IR (KBr) m: 3331 (NH),
1629 (C¼¼O); MS (70 eV) m/z (%): 365.2 (Mþ1, 100); Anal.
calcd for C23H28N2O2: C, 75.79; H, 7.74; N, 7.69. Found: C,
77.70; H, 7.67; N, 7.73.
4d: Yield: 63%; 1H-NMR (CDCl3, 300 MHz) d: 0.97 (s,
6H, 2ꢂCH3), 1.11 (s, 6H, 2ꢂCH3), 2.14–2.21 (m, 4H, C4þC5-
H), 2.47–2.81 (m, 4H, C2þC7-H), 4.05 (br s, 2H, NAH), 5.34
(s, 1H, C9-H), 7.02–7.21 (m, 4H, Ph-H); IR (KBr) m: 3213
(NH), 1565 (C¼¼O); MS (70 eV) m/z (%): 399.2 (Mþ1, 100);
Anal. calcd for C23H27ClN2O2: C, 69.25; H, 6.82; N, 7.02.
Found: C, 69.35; H, 6.90; N, 7.11.
1
4e: Yield: 65%; H-NMR (CDCl3, 300 MHz) d: 1.01 (s, 6H,
2ꢂCH3), 1.11 (s, 6H, 2ꢂCH3), 2.14–2.22 (m, 4H, C4þC5-H),
2.41–2.52 (m, 4H, C2þC7-H), 3.80 (s, 3H, OCH3), 3.96 (s,
3H, OCH3), 4.22 (br s, 2H, NAH), 4.70 (s, 1H, C9-H), 6.70–
6.94 (m, 3H, Ph-H); IR (KBr) m: 3242 (NH), 1596 (C¼¼O);
MS (70 eV) m/z (%): 425.3 (Mþ1, 100); Anal. calcd for
C25H32N2O4: C, 70.73; H, 7.60; N, 6.60. Found: C, 70.65; H,
7.69; N, 6.68.
EXPERIMENTAL
Melting points were determined on an electrothermal appa-
ratus, and the temperature was not calibrated. Microanalysis
was performed by the Perkin-Elmer 2400 Microanalytical
Service. Infrared spectra were recorded as thin films on KBr
using a Perking-Elmer 1700 spectrophotometer. The 1H-NMR
spectra were recorded on a Bruker ARX-300 spectrometer.
Sample solutions were prepared in CDCl3 or DMSO-d6 con-
taining TMS as an internal standard. Mass spectra were
recorded by JMS-DX300 at 70 eV.
4f: Yield: 58%; 1H-NMR (CDCl3, 300 MHz) d: 2.52–2.71
(m, 4H, C4þC5-H), 3.25–3.42 (m, 4H, C2þC7-H), 3.47–3.82
(m, 2H, C3þC6-H), 4.09 (br s, 2H, NAH), 5.35 and 5.39 (each
s, 1H, C9-H), 7.15–7.43 (m, 15H, Ph-H); IR (KBr) m: 3348
(NH), 1660 (C¼¼O); MS (70 eV) m/z (%): 461.3 (Mþ1, 100);
Anal. calcd for C31H28N2O2: C, 80.84; H, 6.13; N, 6.08.
Found: C, 80.89; H, 6.07; N, 6.15.
4g: Yield: 65%; 1H-NMR (CDCl3, 300 MHz) d: 2.51–2.70
(m, 4H, C4þC5-H), 2.76–2.96 (m, 4H, C2þC7-H), 3.27–3.52
(m, 2H, C3þC6-H), 4.14 (br s, 2H, NAH), 5.12 and 5.13 (each
s, 1H, C9-H), 7.06–7.49 (m, 14H, Ph-H); IR (KBr) m: 3296
(NH), 1561 (C¼¼O); MS (70 eV) m/z (%): 495.2 (Mþ1, 100);
Anal. calcd for C31H27ClN2O2: C, 75.22; H, 5.50; N, 5.66.
Found: C, 75.30; H, 5.60; N, 5.10.
All chemical reagents were commercially available and
purified with standard methods before use. Solvents were dried
in routine ways and redistilled. The 5-substituted-1,3-cyclo-
hexanedione 1 was prepared as building block from aromatic
aldehyde, acetone, and diethyl malonate [19a]. A mixture of
5-substituted-1,3-cyclohexanedione (1, 10mmol), aromatic
aldehyde (2, 5mmol), and H2SO4 (0.1 mL) in water (40 mL)
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January 2012 Synthesis of 10-Amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione Derivatives
199
4h: Yield: 61%; 1H-NMR (CDCl3, 300 MHz) d: 2.56–2.80
(m, 4H, C4þC5-H), 2.86–3.00 (m, 4H, C2þC7-H), 3.30–3.53
(m, 2H, C3þC6-H), 4.06 (br s, 2H, NAH), 4.96 and 4.98 (each
s, 1H, C9-H), 7.17–7.98 (m, 14H, Ph-H); IR (KBr) m: 3255
(NH), 1593 (C¼¼O); MS (70 eV) m/z (%): 506.2 (Mþ1, 100);
Anal. calcd for C31H27N3O4: C, 73.65; H, 5.38; N, 8.31.
MS (70 eV) m/z (%): 555.2 (Mþ1, 100); Anal. calcd for
C33H31ClN2O4: C, 71.41; H, 5.63; N, 5.05. Found: C, 71.35;
H, 5.69; N, 5.13.Y 4o: Yield: 50%; 1H-NMR (CDCl3, 300
MHz) d: 2.25–2.40 (m, 4H, C4þC5-H), 2.62–2.90 (m, 4H,
C2þC7-H), 3.14–3.38 (m, 2H, C3þC6-H), 3.75 (s, 3H, OCH3),
3.76 (s, 3H, OCH3), 3.79 (s, 3H, OCH3), 3.81 (s, 3H, OCH3),
4.55 (br s, 2H, NAH), 5.61 and 5.62 (each s, 1H, C9-H), 6.78–
7.43 (m, 12H, Ph-H); IR (KBr) m: 3347 (NH), 1598 (C¼¼O);
MS (70 eV) m/z (%): 581.3 (Mþ1, 100); Anal. calcd for
C35H36N2O6: C, 72.39; H, 6.25; N, 4.82. Found: C, 72.35; H,
6.33; N, 4.75.
1
Found: C, 73.58; H, 5.45; N, 8.25.Y 4i: Yield: 71%; H-NMR
(CDCl3, 300 MHz) d: 2.52–2.71 (m, 4H, C4þC5-H), 3.14–3.41
(m, 4H, C2þC7-H), 3.43–3.58 (m, 2H, C3þC6-H), 3.77 (s, 3H,
OCH3), 3.82 (s, 3H, OCH3), 4.06 (br s, 2H, NAH), 5.30 and
5.34 (each s, 1H, C9-H), 7.07–7.46 (m, 13H, Ph-H); IR (KBr)
m: 3325 (NH), 1653 (C¼¼O); MS (70 eV) m/z (%): 521.3
(Mþ1, 100); Anal. calcd for C33H32N2O4: C, 76.13; H, 6.20;
N, 5.38. Found: C, 76.23; H, 6.13; N, 5.42.
4j: Yield: 82%; 1H-NMR (CDCl3, 300 MHz) d: 2.22–2.39
and 2.58–2.87 (m, 8H, C4þC5þC2þC7-H), 3.13–3.35 (m, 2H,
C3þC6-H), 5.18 (br s, 1H, NAH), 5.55 and 5.60 (each s, 1H,
C9-H), 6.87–7.64 (m, 20H, Ph-H); IR (KBr) m: 3212 (NH),
1650 (C¼¼O); MS (70 eV) m/z (%): 537.3 (Mþ1, 100); Anal.
calcd for C37H32N2O2: C, 82.81; H, 6.01; N, 5.22. Found: C,
82.75; H, 6.09; N, 5.30.
4k: Yield: 80%; 1H-NMR (CDCl3, 300 MHz) d: 2.25–2.40
and 2.62–2.92 (m, 8H, C4þC5þC2þ C7-H), 3.10–3.36 (m, 2H,
C3þC6-H), 5.09 (br s, 1H, NAH), 5.69 and 5.70 (each s, 1H,
C9-H), 6.86–7.41 (m, 19H, Ph-H); IR (KBr) m: 3306 (NH),
1642 (C¼¼O); MS (70 eV) m/z (%): 571.3 (Mþ1, 100); Anal.
calcd for C37H31ClN2O2: C, 77.81; H, 5.47; N, 4.91. Found:
C, 77.75; H, 5.53; N, 4.98.
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4l: Yield: 76%; 1H-NMR (CDCl3, 300 MHz) d: 2.13–2.38
(m, 4H, C4þC5-H), 2.60–2.89 (m, 4H, C2þC7-H), 3.12–3.36
(m, 2H, C3þC6-H), 3.73 (s, 6H, 2ꢂOCH3), 4.99 (br s, 2H,
NAH), 5.55 and 5.57 (each s, 1H, C9-H), 6.69–7.31 (m, 12H,
Ph-H); IR (KBr) m: 3403 (NH), 1663 (C¼¼O); MS (70 eV) m/z
(%): 555.2 (Mþ1, 100); Anal. calcd for C33H31ClN2O4: C,
71.41; H, 5.63; N, 5.05. Found: C, 71.35; H, 5.66; N, 5.15.
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4m: Yield: 83%; H-NMR (CDCl3, 300 MHz) d: 2.20–2.38
(m, 4H, C4þC5-H), 2.58–2.88 (m, 4H, C2þC7-H), 3.12–3.30
(m, 2H, C3þC6-H), 3.75 (s, 3H, OCH3), 3.77 (s, 3H, OCH3),
5.01 (br s, 2H, NAH), 5.58 and 5.60 (each s, 1H, C9-H), 6.69–
7.50 (m, 12H, Ph-H); IR (KBr) m: 3340 (NH), 1639 (C¼¼O);
MS (70 eV) m/z (%): 566.3 (Mþ1, 100); Anal. calcd for
C33H31N3O6: C, 70.07; H, 5.52; N, 7.43. Found: C, 70.03; H,
5.58; N, 7.35.
[13] Srinivas, V.; Swamy, K. C. K. Arkivoc 2009, 7, 31.
[14] Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectro-
metric Identification of Organic Compounds; Wiley: Weinheim, 2005;
p 144.
[15] Pu, L. Chem Rev 2004, 104, 1687.
[16] Ford, P. C.; Cariati, E.; Bourassa, J. Chem Rev 1999, 99, 3625.
ˇ ´
[17] Lukes, V.; Vegh, D.; Hrdlovic, P. Synth Met 2005, 148, 179.
4n: Yield: 74%; 1H-NMR (CDCl3, 300 MHz) d: 2.25–2.42
(m, 4H, C4þC5-H), 2.65–2.93 (m, 4H, C2þC7-H), 3.11–3.35
(m, 2H, C3þC6-H), 3.81 (s, 3H, OCH3), 3.82 (s, 3H, OCH3),
4.55 (br s, 2H, NAH), 5.63 and 5.65 (each s, 1H, C9-H), 6.78–
7.43 (m, 12H, Ph-H); IR (KBr) m: 3484 (NH), 1656 (C¼¼O);
´
[18] Hissler, M.; Lescop, C.; Reau, R. Pure Appl Chem 2007,
79, 201.
[19] (a) Han, G.-F.; Wang, J.-J.; Jiang, G.-J. Chin J Org Chem
2003, 23, 1004 (in Chinese); (b) Wang, R.-H.; Cui, B.; Zhang, W.-T.;
Han, G.-F. Synth Commun 2010, 40, 1867.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet