Fe3+-montmorillonite: An efficient solid catalyst for one-pot synthesis of decahydroacridine derivatives

Article abstract of DOI:10.1002/jccs.200800191

Fe³⁺-montmorillonite was used as a solid acidic catalyst for the synthesis of decahydroacridine derivatives through the condensation of aromatic aldehydes, dimedone and aniline in ethanol. The influence of reaction time, reaction temperature, and the amount of catalyst were studied. All the compounds were characterized by IR, Mp, ¹H NMR and ¹³C NMR analysis.

Full text of DOI:10.1002/jccs.200800191

1280
Journal of the Chinese Chemical Society, 2008, 55, 1280-1285
Fe3+-montmorillonite: An Efficient Solid Catalyst for One-Pot Synthesis of
Decahydroacridine Derivatives
Haitang Luoa,b
Hongyun Niea,b
(
), Yuru Kanga (
),
(
) and Liming Yanga* (
)
aCentre for Eco-material and Green Chemistry, Lanzhou Institute of Chemical Physics,
Chinese Academy of Sciences, Lanzhou 730000, P. R. China
bGraduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. China
Fe3+-montmorillonite was used as a solid acidic catalyst for the synthesis of decahydroacridine deriv-
atives through the condensation of aromatic aldehydes, dimedone and aniline in ethanol. The influence of
reaction time, reaction temperature, and the amount of catalyst were studied. All the compounds were
characterized by IR, Mp, 1H NMR and 13C NMR analysis.
Keywords: Fe3+-montmorillonite; Decahydroacridine derivatives; Solid acid catalysts; Aromatic
aldehyde; Dimedone.
INTRODUCTION
In recent years, the use of solid acidic catalysts, such
dehydes with acetic anhydride,8 etc.
1,4-Dihydropyridine (1,4-DHPs) and their deriva-
tives have attracted strong interest due to their pharmaco-
logical activity as the most important class of the calcium
channel modulators. Different catalysis systems, such as
3,4,5-trifluorobenzeneboronic acid in ionic liquid,9 tetra-
butylammonium hydrogen sulfate,10 iodotrimethylsilane,11
iodine,12 and silica gel/NaHSO4,13 have been used for their
synthesis. Recently, chemists have paid more attention to
1,4-DHPs derivatives with different substituents,14 in order
to explore the structure-activity relationship of these com-
pounds. Herein we report the synthesis of some decahydro-
acridine derivatives bearing DHPs (5) in the presence of
the catalyst of Fe3+-montmorillonite, as shown in Scheme I.
To our knowledge, some of these compounds (5) are re-
ported for the first time in the literature.
as montmorillonite clays, have received considerable atten-
tion in different areas of organic synthesis, because of their
environmental compatibility, reusability, operational sim-
plicity, non-toxicity, non-corrosiveness, low cost and the
ease of isolation.1 As solid acidic catalysts, montmorillo-
nite clays act as both Brønsted and Lewis acids in their nat-
ural forms,2 which enable them to function as acidic cata-
lysts. Cation treated montmorillonite with transition metal
ions can result in the change in acidities, which has given
them an acidity-tunable property. This type of montmoril-
lonite has been used for many typical acid-catalyzed reac-
tions such as Friedel-Crafts reaction,3 Beckmann rear-
rangement,4 Paal-Knorr condensation,5 esterification,6
synthesis of phenylacetates,7 the protection of aromatic al-
Scheme I Synthesis of 1,8-dioxo-decahydroacridine derivatives catalyzed by Fe3+-montmorillonite
* Corresponding author. Tel: +86-931-8277635; Fax: +86-931-8277088; E-mail: limy@lzb.ac.cn

Synthesis of Decahydroacridine Using One-Pot Method
J. Chin. Chem. Soc., Vol. 55, No. 6, 2008 1281
RESULTS AND DISCUSSION
Table 1. Condensation of benzaldehyde, dimedone and aniline
catalyzed by different catalystsa
Initially, the condensation of benzaldehyde, dimedone
and aniline was selected as the model reaction to be studied
in ethanol at 80 °C for 6 h, by using different metal-ex-
changed montmorillonites and K10 as catalysts, separately.
The results are listed in Table 1. It was obvious that Fe3+-
montmorillonite appeared more active compared with other
clay catalysts. The catalytic activities of the examined
montmorillonite clays were gradually decreased in the fol-
lowing order: Fe3+ > Co2+ > Zn2+ > Al3+ > Cu2+-montmoril-
lonite > montmorillonite K10. However, almost no pro-
spective product 5a could be obtained after 6 h under cata-
lyst-free conditions, and only intermediate 4a (Mp 198-
200 °C) was obtained in 38% yield (Table 1, entry 7). Con-
sequently, the mechanism of the reaction could be de-
scribed as follows:15 intermediate 4a was formed firstly by
Knoevenagel addition and then attacked by the NH2 group
of aniline. Subsequently, 4a was cyclized by elimination of
water and product 5a was obtained. In these processes,
Fe3+-montmorillonite played a crucial role in accelerating
the reaction, especially for water elimination of intermedi-
ate. It could be verified by the fact that reaction under cata-
lyst-free conditions gave a product of intermediate 4a.
On the basis of the above exploration, the effects of
catalyst amount, temperature and reaction time were also
studied on the model reaction, and the results are listed in
Table 2. Obviously, all the factors had much effect on the
condensation. With the increase in catalyst amount, reac-
tion temperature and reaction time, the yield also increased.
The optimized condition was 15 wt% (based on aldehyde)
of Fe3+-montmorillonite, 80 °C and 6 h, under which prod-
uct 5a could be obtained in 92%.
Entry
Catalysta
Time (h)
Yield (%)b
1
2
3
4
5
6
7
Fe3+-mont
Co2+-mont
Zn2+-mont
Cu2+-mont
Al3+-mont
K10
6
92
84
6
6
70
6
66
6
6
60
56
38 (46)c
None
6 (12)
a Reaction conditions: the amount of catalyst was 15 wt% (based
on benzaldehyde), reaction temperature: 80 °C, solvent: EtOH.
b Isolated yield of 5a.
c Isolated yield of intermediate 4a.
Table 2. Conditions optimization for the condensation among
benzaldehyde, dimedone and aniline over Fe3+-
montmorillonite catalysta
Catalyst amount Temperature
Entry
Time (h) Yield (%)b
(wt%)
(°C)
1
2
3
4
5
6
8
9
20
15
10
05
15
15
15
15
80
80
6
6
6
6
6
6
2
4
94
92
83
68
95
71
68
80
80
80
1000
60
80
80
a Reaction conditions: benzaldehyde (1 mmol), dimedone (2
mmol) and aniline (1 mmol) Fe3+-montmorillonite catalyst (15
wt% based on benzaldehyde) and EtOH as a solvent.
b Isolated yield of 5a.
(except 5j15) have not been reported in the literature.
Because Fe3+-montmorillonite was a solid material, it
could be easily recycled after reaction by simple filtration.
After washing and activating at 120 °C for 5 h, the catalyst
had been further examined in next run; the result indicated
that the catalyst could be reused four times and without sig-
nificant loss of its activity. (Table 3, entry 1).
Furthermore, other aldehydes and aromatic amines
have been subjected to the abovementioned optimized con-
ditions, and the results are listed in Table 3. The aromatic
aldehydes reacted well with aniline to give the correspond-
ing decahydroacridine in the yields ranging from 80% to
92% over the Fe3+-montmorillonite catalyst. The substitu-
ents on the aromatic ring seemed to have some effects on
the yield but no obvious regulation was shown for their
electronic nature. Importantly, in this system, such acid-la-
bile substrates as 4-methoxybenzaldehyde, vanillin and
piperonal all worked well. When the aliphatic aldehyde
was performed, the yield was low. (Table 3, entry 12).
However, cinnamaldehyde had the electronic effect analo-
gous to –CHO grafted on the benzene ring and gave a good
yield. It is worth pointing out that these decahydroacridines
CONCLUSIONS
Using Fe3+-montmorillonite as a catalyst, 1,8-dioxo-
9-aryl-10-(4-phenyl)-decahydroacridine and their deriva-
tives were synthesized successfully from aromatic alde-
hydes, dimedone and aniline with high yields. To the best
of our knowledge, the synthesis of most of these com-
pounds are reported in the literature for the first time. The
experimental procedure offered the advantages of opera-

1282 J. Chin. Chem. Soc., Vol. 55, No. 6, 2008
Luo et al.
Table 3. The synthesis of various 1,8-dioxo-decahydroacridines and their derivatives
catalyzed by Fe3+-montmorillonitea
Entry
1
Aldehyde
Amine
Products Yield (%)b
Mp (°C)
CHO
NH2
5a
5b
92 (89c)
82
200-205
CHO
NH2
NH2
2
3
200-205
216-218
Cl
CHO
CHO
5c
86
O2N
NH2
NH2
NH2
4
5
6
5d
5e
5f
77
79
87
234-235
242-245
292-295
HO
HO
CHO
CHO
H3CO
HO
CHO
NH2
7
5g
78
252-255
O
O
CHO
NH2
NH2
8
5h
5i
93
81
95
276-279
271-273
265-267
H3CO
CH CH CHO
9
NH2
CHO
10
5j
H3C
NH2
CHO
11
12
5k
5l
72
32
219-221
192-194
C2H5O
NH2
CHO
a All reactions were carried out at 80 °C for 6 hours.
b Isolated yields.
c The catalyst was reused for the fourth time.
tional simplicity, the ease of catalyst separation, and good
catalyst recycling.
nol. This ethanol solution was then put into a 100 mL beaker
containing approx. 50 mL ice water, and the crude product
was obtained. The pure product could be obtained by re-
crystallization in ethanol. Data of compounds is shown be-
low.
EXPERIMENTAL
Representative procedure for the synthesis of
acridine and their derivatives
Analytical data for compounds
Benzaldehyde (1 mmol), dimedone (2 mmol), aniline
(1 mmol) and Fe3+-montmorillonite catalyst (15 wt% based
on benzaldehyde) were added in ethanol (5 mL) in a round
bottom flask, and stirred at 80 °C for 6 hours. After reac-
tion, the solid catalyst was filtered and washed with etha-
3,3,6,6-Tetramethyl-1,8-dioxo-9-benzene-10-(4-phenyl)-
decahydroacridine (5a)16
White solid, mp: 200-205 °C. IR (KBr): 3104, 2962,
2872, 1643, 1595, 1492, 1447, 1375, 1301, 1251, 1167,
1
1045, 870, 777, 722, 696 cm-1. H NMR (300 MHz,

Synthesis of Decahydroacridine Using One-Pot Method
J. Chin. Chem. Soc., Vol. 55, No. 6, 2008 1283
CDCl3): 0.88 (s, 6H, 2CH3), 0.98 (s, 6H, 2CH3), 2.19 (d,
2H, J = 16.0 Hz, HAB, H-4a, H-5a), 2.28 (d, 2H, J = 16.0
Hz, HAB, H-4e, H-5e), 2.44 (q, 4H, J = 9.8 Hz, 2CH2, H-2,
H-7), 5.541 (s, 1H, H-9), 7.01 (s, 1H, ArH), 7.08 (d, J = 6.4
Hz, 2H, ArH), 7.14-7.34 (m, 5H, ArH), 7.48 (d, J = 6.4 Hz,
2H, ArH). 13C NMR (125 MHz, CDCl3, ppm): d 212.2,
150.8, 145.1, 136.8, 131.5, 130.1, 128.6, 126.6, 126.1,
125.8, 124.2, 51.2, 42.9, 35.6, 23.1, 22.6. Anal Calcd for
C29H31NO2: C 81.88, H 7.29. Found: C 81.72, H 7.39.
3,3,6,6-Tetramethyl-1,8-dioxo-9-(4-Chlorophenyl)-10-
(4-phenyl)-decahydroacridine (5b)
2H, ArH), 9.11 (s, 1H, OH). 13C NMR (125 MHz, CDCl3,
ppm): d 212.5, 161.4, 153.7, 151.1, 146.1, 137.9, 135.8,
132.5, 129.9, 128.3, 125.7, 51.8, 42.6, 35.8, 23.1, 22.5.
Anal Calcd for C29H31NO3: C 75.91, H 7.03. Found: C
75.82, H 7.13.
3,3,6,6-Tetramethyl-1,8-dioxo-9-(3-hydroxyphenyl)-10-
(4-phenyl)-decahydroacridine (5e)
White solid, mp: 240-246 °C. IR (KBr): 3425, 2959,
2926, 2869, 1669, 1595, 1512, 1445, 1403, 1371, 1254,
1168, 1041, 1014, 833, 755, 736, 589 cm-1. 1H NMR (300
MHz, CDCl3): 0.81 (s, 6H, 2CH3), 0.99 (s, 6H, 2CH3), 1.55
(d, J = 17.6 Hz, 2H, HAB, H-4a, H-5a), 2.27 (d, J = 17.6, 2H,
White solid, mp: 202-204 °C. IR (KBr): 3101, 2958,
2869, 1639, 1594, 1489, 1469, 1373, 1300, 1251, 1153,
H
AB, H-4e, H-5e), 2.43 (q, J = 16.4 Hz, 4H, HAB, 2CH2,
1
1093, 829, 777, 586 cm-1. H NMR (300 MHz, CDCl3):
H-2, H-7), 5.47 (s, 1H, H-9), 5.97 (s, 1H, OH), 6.74 (d, J =
6.4 Hz, 2H, ArH), 7.04-7.34 (m, 4H, ArH), 7.51 (d, J = 6.0
Hz, 2H, ArH), 9.11 (s, 1H, OH). 13C NMR (125 MHz,
CDCl3, ppm): d 213.1, 212.4, 160.7, 151.7, 150.9, 147.2,
146.4, 137.8, 136.5, 135.8, 134.7, 132.5, 132.1, 130.6,
129.9, 125.8, 125.2, 122.3, 121.8, 52.9, 51.9, 50.8, 43.1,
42.6, 35.8, 34.4, 23.3, 23.2, 22.3. Anal Calcd for
C29H31NO3: C 78.91, H 7.03. Found: C 78.78, H 7.13.
3,3,6,6-Tetramethyl-1,8-dioxo-9-(4-hydroxy-3-methoxy-
phenyl)-10-(4-phenyl)-decahydroacridine (5f)16
0.88 (s, 6H, 2CH3), 0.99 (s, 6H, 2CH3), 1.54 (d, 2H, J =
16.8 Hz, HAB, H-4a, H-5a), 2.28 (d, 2H, J = 16.8 Hz, HAB
,
H-4e, H-5e), 2.40 (q, 4H, J = 14.6, 2CH2, H-2, H-7), 5.47
(s, 1H, H-9), 7.00 (s, 1H, ArH), 7.01 (d, J = 7.6 Hz, 2H,
ArH), 7.10-7.34 (m, 4H, ArH), 7.48 (d, J = 6.4 Hz, 2H,
ArH). 13C NMR (125 MHz, CDCl3, ppm): d 213.6, 153.7,
151.4, 146.1, 137.3, 135.7, 132.3, 129.9, 128.1, 126.2,
125.6, 51.4, 42.7, 35.5, 23.1, 22.3. Anal Calcd for
C29H30NO2Cl: C 75.73, H 6.53. Found: C 75.65, H 6.79.
3,3,6,6-Tetramethyl-1,8-dioxo-9-(4-nitrophenyl)-10-(4-
phenyl)-decahydroacridine (5c)16
White solid, mp: 292-295 °C. IR (KBr): 3442, 2956,
2868, 1629, 1581, 1510, 1485, 1440, 1378, 1273, 1233,
1196, 1140, 1008, 927, 768, 649 cm-1. 1H NMR (300 MHz,
CDCl3): 0.88 (s, 6H, 2CH3), 0.99 (s, 6H, 2CH3), 1.55 (d, J =
White solid, mp: 216-218 °C. IR (KBr): 3075, 2962,
2928, 2870, 1638, 1595, 1492, 1447, 1375, 1300, 1250,
1167, 1045, 870, 777, 722, 695 cm-1. 1H NMR (300 MHz,
CDCl3): 0.85 (s, 6H, 2CH3), 1.10 (s, 6H, 2CH3), 1.54 (d, J =
17.2 Hz, 2H, HAB, H-4a, H-5a), 1.97 (d, J = 17.2, 2H, HAB
,
H-4e, H-5e), 2.45 (q, J = 16.4 Hz, 4H, HAB, 2CH2, H-2,
H-7), 3.77 (s, 3H, OCH3), 5.45 (s, 1H, H-9), 6.12 (s, 1H,
OH), 6.75-6.91 (m, 2H, ArH), 7.12 (d, J = 10.4 Hz, 2H,
ArH), 7.26 (s, 1H, ArH), 7.48 (d, J = 10.4 Hz, 2H, ArH).
13C NMR (125 MHz, CDCl3, ppm): d 212.6, 212.3, 164.7,
157.3, 151.2, 147.3, 146.6, 137.9, 137.3, 135.8, 134.9,
133.5, 132.6, 130.6, 126.7, 125.8, 125.3, 122.9, 121.8,
53.2, 52.4, 50.8, 43.3, 42.8, 35.8, 34.9, 23.6, 23.3, 22.6,
22.2. Anal Calcd for C30H33NO4: C 76.43, H 7.01. Found:
C 76.52, H 6.93.
16.2 Hz, 2H, HAB, H-4a, H-5a), 2.28 (d, J = 16.2, 2H, HAB
,
H-4e, H-5e), 2.40 (q, J = 14.6 Hz, 4H, HAB, 2CH2, H-2,
H-7), 5.54 (s, 1H, H-9), 7.03 (s, 1H, ArH), 7.10 (d, J = 6.4
Hz, 2H, ArH), 7.11-7.34 (m, 4H, ArH), 7.48 (d, J = 6.4 Hz,
2H, ArH). 13C NMR (125 MHz, CDCl3, ppm): d 213.1,
153.7, 150.9, 146.4, 137.8, 135.8, 132.5, 129.9, 128.2,
126.3, 125.8, 51.9, 42.4, 35.8, 23.3, 22.7. Anal Calcd for
C29H30N2O4: C 74.04, H 6.38. Found: C 74.22, H 6.13.
3,3,6,6-Tetramethyl-1,8-dioxo-9-(4-hydroxyphenyl)-10-
(4-phenyl)-decahydroacridine (5d)
3,3,6,6-Tetramethyl-1,8-dioxo-9-(3,4-methylendioxy-
phenyl)-10-(4-phenyl)-decahydroacridine (5g)
White solid, mp: 234-235 °C. IR (KBr): 3439, 2958,
2926, 2868, 1665, 1593, 1511, 1468, 1403, 1389, 1265,
1155, 1043, 833, 755, 736, 697 cm-1. 1H NMR (300 MHz,
CDCl3): 0.87 (s, 6H, 2CH3), 0.98 (s, 6H, 2CH3), 1.55 (d, J =
White solid, mp: 250-255 °C. IR (KBr): 3440, 2959,
2926, 2868, 1653, 1595, 1503, 1488, 1446, 1376, 1308,
1232, 1153, 1039, 934, 811, 600 cm-1. 1H NMR (300 MHz,
CDCl3): 0.85 (s, 6H, 2CH3), 1.10 (s, 6H, 2CH3), 1.54 (d,
2H, J = 16.8 Hz, HAB, H-4a, H-5a), 2.10 (d, 2H, J = 16.8
17.6 Hz, 2H, HAB, H-4a, H-5a), 2.21 (d, J = 17.6, 2H, HAB
,
H-4e, H-5e), 2.39 (q, J = 16.4 Hz, 4H, HAB, 2CH2, H-2,
H-7), 5.54 (s, 1H, H-9), 5.99 (s, 1H, OH), 7.10 (d, J = 6.4
Hz, 2H, ArH), 7.24-7.48 (m, 4H, ArH), 7.48 (d, J = 6.0 Hz,
Hz, HAB, H-4e, H-5e), 2.38 (q, J = 14.6, 4H, 2CH2, HAB
,
H-2, H-7), 5.46 (s, 1H, H-9), 5.91 (s, 2H, OCH2O), 6.57-

1284 J. Chin. Chem. Soc., Vol. 55, No. 6, 2008
Luo et al.
6.69 (m, 2H, ArH), 7.26 (d, J = 9.6 Hz, 2H, ArH), 7.34 (s,
1H, ArH), 7.48 (d, J = 9.6 Hz, 2H, ArH). 13C NMR (125
MHz, CDCl3, ppm): d 212.2, 147.4, 145.1, 136.8, 131.5,
130.1, 128.6, 126.6, 125.7, 125.1, 101.7, 53.2, 51.2, 42.1,
35.3, 23.2, 22.9. Anal Calcd for C30H31NO4: C 76.76, H
6.61. Found: C 76.65, H 6.89.
146.4, 137.8, 135.8, 132.5, 129.9, 128.2, 126.3, 125.8,
51.9, 42.4, 35.8, 23.3, 21.5. Anal Calcd for C30H33NO2: C
82.00, H 7.52. Found: C 82.06, H 7.46.
3,3,6,6-Tetramethyl-1,8-dioxo-9-benzene-10-(4-ethoxy-
phenyl)-decahydroacridine (5k)
White solid, mp: 219-221 °C. IR (KBr): 3075, 2962,
2830, 2870, 1673, 1595, 1492, 1447, 1375, 1299, 1250,
1168, 871, 777, 721, 695 cm-1. 1H NMR (300 MHz, CDCl3):
0.88 (s, 6H, 2CH3), 0.91 (m, 3H, CH3), 1.10 (s, 6H, 2CH3),
1.54 (d, 2H, J = 16.0 Hz, 2H, HAB, H-4a, H-5a), 2.28 (d, 2H,
3,3,6,6-Tetramethyl-1,8-dioxo-9-(4-methoxyphenyl)-10-
(4-phenyl)-decahydroacridine (5h)16
White solid, mp: 282-284 °C. IR (KBr): 3101, 2958,
2922, 2869, 1665, 1626, 1601, 1586, 1511, 1464, 1360,
1284, 1262, 1197, 1035, 841, 745, 684 cm-1. 1H NMR (300
MHz, CDCl3): 0.82 (s, 6H, 2CH3), 1.01 (s, 6H, 2CH3), 1.53
(d, 2H, J = 16.8 Hz, HAB, H-4a, H-5a), 2.22 (d, 2H, J = 16.8
Hz, HAB, H-4e, H-5e), 2.47 (q, 4H, J = 14.6, 2CH2, H-2,
H-7), 3.78 (s, 3H, OCH3), 5.49 (s, 1H, H-9), 6.80 (s, 1H,
ArH), 7.01 (d, J = 7.6 Hz, 2H, ArH), 7.26-7.34 (m, 3H,
ArH), 7.48 (d, J = 6.4 Hz, 2H, ArH). 13C NMR (125 MHz,
CDCl3, ppm): d 212.8, 165.8, 149.7, 148.5, 147.2, 137.9,
135.6, 132.5, 129.8, 128.5, 126.3, 125.7, 52.7, 51.9, 42.4,
35.8, 23.3, 22.1. Anal Calcd for C30H33NO3: C 79.12, H
7.25. Found: C 79.45, H 7.09.
J = 16.0 Hz, HAB, H-4e, H-5e), 2.44 (q, J = 9.8 Hz, 4H, HAB
,
2CH2, H-2, H-7), 4.79 (m, 2H, CH2), 5.54 (s, 1H, H-9),
7.08 (d, J = 6.4 Hz, 2H, ArH), 7.14-7.34 (m, 5H, ArH), 7.48
(d, J = 6.4 Hz, 2H, ArH). 13C NMR (125 MHz, CDCl3,
ppm): d 213.1, 151.7, 150.9, 146.4, 137.8, 135.8, 132.5,
129.9, 128.2, 126.3, 125.8, 65.6, 51.9, 42.4, 35.8, 23.3,
15.2. Anal Calcd for C31H35NO3: C 79.32, H 7.46. Found:
C 79.43, H 7.40.
3,3,6,6-Tetramethyl-1,8-dioxo-9-heptyl-10-(4-phenyl)-
decahydroacridine (5l)
White solid, IR (KBr): 3104, 2964, 2870, 1637, 1594,
1486, 1447, 1375, 1311, 1252, 1161, 1045, 872, 772, 726,
698 cm-1. 1H NMR (300 MHz, CDCl3): 0.87 (s, 12H, 4CH3),
0.89 (m, 3H, CH3), 1.53 (m, 10H, 5CH2), 1.61 (m, 2H,
CH2), 1.83 (d, J = 16.0 Hz, 2H), 2.14 (d, J = 16.0 Hz, 2H),
2.44 (q, J = 9.8 Hz, 4H, 2CH2), 5.52 (s, 1H, H-9), 7.01 (m,
3,3,6,6-Tetramethyl-1,8-dioxo-9-(4-propenylphenyl)-10-
(4-phenyl)-decahydroacridine (5i)
White solid, mp: 270-275 °C. IR (KBr): 3442, 2957,
2868, 1670, 1623, 1596, 1514, 1495, 14689, 1378, 1269,
1250, 1220, 1152, 1030, 886, 781, 699 cm-1. 1H NMR (300
MHz, CDCl3): 0.85 (s, 6H, 2CH3), 0.92 (s, 6H, 2CH3), 1.55
(d, 2H, J = 16.8 Hz, HAB, H-4a, H-5a), 2.09 (d, 2H, J = 16.8
Hz, HAB, H-4e, H-5e), 2.47 (q, 4H, J = 14.6, 2CH2, H-2,
H-7), 4.54 (s, 2H, CH=CH), 5.54 (s, 1H, H-9), 7.08 (s, 1H,
ArH), 7.11 (d, J = 9.6 Hz, 2H, ArH), 7.26-7.34 (m, 5H,
ArH), 7.48 (d, J = 9.6 Hz, 2H, ArH). 13C NMR (125 MHz,
CDCl3, ppm): d 212.7, 150.7, 149.9, 146.4, 142.1, 137.8,
136.9, 135.8, 132.5, 129.9, 128.2, 126.3, 125.8, 52.4, 42.5,
35.8, 23.2. Anal Calcd for C31H33NO2: C 77.18, H 6.85.
Found: C 77.21, H 7.01.
2H, ArH), 7.24-7.38 (m, 2H, ArH), 7.41 (m, 1H, ArH). 13
C
NMR (125 MHz, CDCl3, ppm): d 213.1, 152.1, 151.4,
135.8, 129.9, 129.1, 126.3, 51.9, 38.2, 45.3, 42.4, 35.8,
31.8, 29.4, 29.1, 25.8, 23.3, 22.7, 22.2, 14.3. Anal Calcd
for C30H41NO2: C 80.54, H 9.17. Found: C 80.72, H 9.13.
Received April 10, 2008.
REFERENCES
1. (a) Vaccari, A. Catal. Today 1998, 41, 53-71. (b) Gil, A.;
Gandia, L.-M.; Vicente, M.-A. Catal. Rev.-Sci. Eng. 2002,
42, 145-212. (c) Varma, R.-S. Tetrahedron 2002, 58, 1235-
1255.
3,3,6,6-Tetramethyl-1,8-dioxo-9-benzene-10-(4-methyl-
phenyl)-decahydroacridine (5j)
White solid, mp: 262-263 °C. IR (KBr): 3075, 2959,
2869, 1661, 1594, 1522, 1492, 1374, 1303, 1264, 1222,
1165, 1043, 818, 696 cm-1. 1H NMR (400 MHz, CDCl3):
0.80 (s, 6H, 2CH3), 0.94 (s, 6H, 2CH3), 2.34 (d, 2H, J =
16.0 Hz, 2H, HAB, H-4a, H-5a), 2.39 (d, 2H, J = 16.0 Hz,
2. Laszlo, P. Science 1987, 235, 1473.
3. (a) Laszlo, P.; Mathy, A.-H. Chim. Acta. 1987, 70, 577-586.
(b) Choudary, B.-M.; Rao, B.-P.; Chowdari, N.-S.; Kantam,
M.-L. Catal. Commun. 2002, 3, 363-367.
4. Pai, S.-G.; Baipai, A.-R.; Deshpande, A.-B. Synth. Commun.
1997, 27, 379-384.
H
AB, H-4e, H-5e), 2.44 (q, J = 9.8 Hz, 4H, HAB, 2CH2, H-2,
H-7), 5.54 (s, 1H, H-9), 7.08 (d, J = 6.4 Hz, 2H, ArH),
7.11-7.40 (m, 5H, ArH), 7.48 (d, J = 6.4 Hz, 2H, ArH). 13
NMR (125 MHz, CDCl3, ppm): d 213.1, 151.2, 150.9,
5. Song, G.-Y; Wang, B.; Wang, G.; Yang, L.-Y. Synth.
Commun. 2005, 35, 1051-1057.
C
6. (a) Choudhary, V.-R.; Mantri, K.; Jana, S.-K. Catal.

Synthesis of Decahydroacridine Using One-Pot Method
J. Chin. Chem. Soc., Vol. 55, No. 6, 2008 1285
Commun. 2001, 2, 57-61. (b) Kantam, M.-L.; Bhaskar, V.;
Choudary, B.-M. Catal. Lett. 2002, 78, 185-188.
7. Reddy, C.-R.; Vijayakumar, B.; Prakash, B.-S. J. MoL.
Catal A: Chem. 2004, 223, 117-122.
1997, 53, 2803-2816. (e) Kappe, C.-O. Tetrahedron 1993,
49, 6937-6963. (f) Belmont, P.; Andrez, J.-C.; Allan, C.-S.
Tetrahedron Lett. 2004, 45, 2783-2786. (g) Papagni, A.-P.;
Buttero, D.; Moret, M.; Sassella, A.; Miozzo, L.; Ridolfi, G.
Chem. Mater. 2003, 15(26), 5010-5018. (h) Goossen, R.;
Smet, M.; Dehaen, W. Tetrahedron Lett. 2002, 43, 6605-
6608.
8. Jankovic, L.; Komadel, P. J. Catal. 2003, 218, 227.
9. Sridhar, R.; Perumal, P.-T. Tetrahedron 2005, 9, 2465-2470.
10. Tewari, N.; Dwivedi, N.; Tripathi, R.-P. Tetrahedron Lett.
2004, 49, 9011-9014.
15. Jin, T.-S.; Zhang, J.-S.; Guo, T.-T.; Wang, A.-Q.; Li, T.-S.
Synthesis 2004, 12, 2001-2005.
11. Sabitha, G.; Reddy, G.-S.; Reddy, K.-K; Ch, S. Tetrahedron
Lett. 2003, 44, 4129-4131.
16. (a) Bakibaev, A.-A. Russ. J. Org. Chem. 1994, 30, 1109-
1112. (b) Ashry, E.-S.; Awad, L.-F.; Ibrahim, S.-I.; Bdeewy,
O.-K. Arkivoc 2006, 178-186. (c) Nekrasov, D.-D.; Koltsova,
S.-V.; Radishevskaja, M.-A. Chem. Heterocyl. Compd.
(Engl. Transl.) 2004, 40, 375. (d) Shirinian, V.-Z.; Krayushkin,
M.-M.; Belen’kii, L.-I.; Vorontsova, L.-G.; Starikova, Z.-A.;
Martynkin, A. Chem. Heterocyl. Compd. (Engl. Transl.)
2001, 37, 1228.
12. Ko, S.; Sastry, M.-N.; Lin, C.; Yao, C.-F. Tetrahedron 2005,
34, 5771-5774.
13. Chari, M.-A.; Syamasundar, K. Catal. Commun. 2005, 9,
624-626.
14. (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1-42. (b)
Stout, D.-M.; Meyers, A.-I. Chem. Rev. 1982, 82, 223-243.
(c) Chorvat, R.-J.; Rorig, K.-J. J. Org. Chem. 1988, 53,
5779-5781. (d) Kappe, C.-O.; Fabian, W.-M. Tetrahedron