An efficient one-pot synthesis of polyhydrobenzoacridine-1-one derivatives under microwave irradiation without catalyst

Article abstract of DOI:10.1002/jhet.5570430629

A series of 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[c] acridine-1-ones and 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[a] acridine-1-ones were synthesized by the reaction of an aldehyde, α-naphthylamine or β-naphthylamine and dim

Full text of DOI:10.1002/jhet.5570430629

Nov-Dec 2006
An Efficient One-pot Synthesis of Polyhydrobenzoacridine-1-one
Derivatives under Microwave Irradiation without Catalyst
1621
Shujiang Tu,* Runhong Jia, Bo Jiang, Yan Zhang, Junyong Zhang
Department of Chemistry, Xuzhou Normal University, Key Laboratory of Biotechnology on Medical
Plant, Xuzhou; Jiangsu, 221009, P. R. China
Received March 22, 2006
NH2
O
R
O
O
95%EtOH
MWI
RCHO
+
+
+
N
H
1
2
5
3
4
NH2
O
R
O
O
95%EtOH
MWI
RCHO
+
N
H
1
3
6
A
series of 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[c]acridine-1-ones ꢀꢁꢂ 3,3-
dimethyl-9-substituted-1,2,3,4,9,10-hexahydrobenzo[a]acridine-1-ones were synthesized by the reaction of
an aldehyde, ꢀꢃnaphthylamine or ꢁꢃnaphthylamine and dimedone under microwave irradiation with short
times and high yields.
J. Heterocyclic Chem., 43, 1621 (2006).
A lot of natural and synthetic compounds containing
Kidwai and S. Rastogi have reported the synthesis of
polyhydroacridinones without additional fused
benzene rings [12]. Here, we would like to report a
highly efficient method for the one-pot synthesis of a
series of 3,3-dimethyl-9-substituted-1,2,3,4,9,10-hexa-
hydrobenzo[c]acridine-1-ones and 3,3-dimethyl-9-
substituted-1,2,3,4,9,10-hexahydrobenzo[a]acridine-1-
ones under microwave irradiation without catalyst.
The products were synthesized by equimolecular
amounts of naphthylamine, dimedone and aldehyde
without catalyst in a small amount of ethanol (95%)
under microwave irradiation (Scheme 1). After
irradiation for 4-19 min, the polyhydrobenzoacridine-
1-one derivatives were obtained in excellent yields
(75-98%). Besides, compared with the traditional
heating methodology, when 1a, 2 and 3 in ethanol
were irradiated with microwave, the reaction time was
shortened to 6 min from 12 hours [8,9]. The results
were listed in Table 1 and Table 2.
the acridine skeleton display interesting biological and
physical activities, such as antimalaria [1] and
antitumor agents [2], and multihydroacridineone
derivatives have been reported to have high
fluorescence efficiency and can be used as fluorescent
molecular probes for monitoring of polymerization
process [3]. They are also increasingly receiving
attention due to their likeness in properties with those
of 1,4-dihydropyridines, which have similarities in
structure to the biologically important compounds
such as NADH and NADPH [4]. As a consequence,
the interest of organic chemists in the synthesis or
structure modifications of acridinedione derivatives
remains high. Recently, there are many other methods
available for the construction of benzoacridine
derivatives, for instance, by refluxing appropriate
naphthylamine, dimedone and aldehyde in C6H6 [5],
EtOH [6,7] or H2O [8,9]. But these reactions need long
reaction times (2-18 hours) [5,8] and complicated
route that naphthylamine and aldehyde need to be
condensed to schiff’s base firstly [8]. Microwave
irradiation (MWI) is a very useful technique in organic
synthesis [10]. It is a simple, timesaving, high yielding,
and environmentally friendly process. We have
already reported the synthesis of heterocyclic
compounds under microwave irradiation [11]. M.
Results and Discussion.
The procedure is easy to operate and the workup
procedure is just simple filtrations. Furthermore, we found
that this protocol can be applied not only for the aromatic
aldehydes with either electron-withdrawing groups or
electron-donating groups, but also for heterocyclic and
aliphatic aldehydes.

1622
S. Tu, R. Jia, B. Jiang, Y. Zhang, J. Zhang
Vol 43
Table 1
Physical Data of Compounds 4
Conventional [d]
Reaction time Yield
Compound
No.
Microwave-assisted
Time (lit.)
(min)
R
Yield (lit.) (%)[a]
Mp (lit.) (°C)[b]
(h)
2
(%)
85
4a
4b
4c
4d
4e
4f
4-ClC6H4
4-BrC6H4
6 (12h)[c]
98(93)[c]
92 (91)[c]
98 (98)[c]
82
276-277 (263-266)[c]
276.6-277 (276-278)[c]
>300 (273-275)[c]
269.2-271
7 (12h)[c]
6 (12h)[c]
13
2.5
2
81
88
75
78
73
85
81
88
80
2-ClC6H4
3
4-FC6H4
3
2,4-Cl2C6H3
3,4-Cl2C6H3
3, 4-OCH2OC6H3
4-OCH3C6H4
2, 3-(CH3O)2C6H3
3, 4-(CH3O)2C6H3
3-CH3O-4-OHC6H4
4-NO2C6H4
11(12h)[c]
16 (12h)[c]
19 (18h)[c]
13 (18h)[c]
9
87
>300 (280-282)[c]
>300 (284-286)[c]
>300 (283-285)[c]
257-259 (260-262)[c]
298-299
92 (90)[c]
95 (89)[c]
93 (89)[c]
95
3
3.5
3
4g
4h
4i
2
14 (18h)[c]
93 (93)[c]
255-256 (246-247)[c]
2.5
4j
4k
4l
16
85
270-273
2.5
2
78
82
86
71
72
7
95 (93)[c]
95 (95)[c]
75
295-296 (280-282)[c]
280-283 (267-269)[c]
259-261
4m
4n
4o
3-NO2C6H4
11 (12h)[c]
2.5
2
C4H3S
6
CH3(CH2)3
15
80
162-164
3
.
Table 2
Physical Data of Compounds 6
Compound
No.
Microwave-assisted
Conventional [d]
Reaction time Yield
R
Time (min)
(lit.)
Yield (lit.)
(%)[a]
Mp (lit.) (°C) [b]
(h)
(%)
1.5
85
6a
6b
6c
6d
6e
6f
4-ClC6H4
4-BrC6H4
8 (3h)[c]
8 (4h)[c]
9 (5h)[c]
4
98 (98)[c]
95 (87)[c]
98 (97)[c]
93
>300 (>300)[c]
1.5
2
81
85
79
86
79
78
78
77
85
84
>300
4-OCH3C6H4
3, 4-OCH2OC6H3
3, 4-(CH3O)2C6H3
C6H5
>300 (297-298)[c]
>300
1
5 (10h)[c]
97(96)[c]
293-296
>300
1.5
1.5
2
6
93
6g
6h
6i
4-NO2C6H4
8
92
246-248
294-296
296-298
>300
2
3-NO2C6H4
9
92
1
3-CH3O-4-OHC6H4
4 (12h)[c]
5 (5h)[c]
92 (99)[c]
98 (98)[c]
1
6j
C4H3S
4-(benzo[d]oxazol-2-
yl)C6H4
1
6k
5
96
>300
2
2
79
72
6l
3-indole
7
9
90
81
>300
6m
CH3(CH2)3
186-188
[a] Yields of isolated compounds; [b] Melting points are uncorrected; [c] Known compounds (4a, 4b, 4c, 4h, 4l, 6a, 6c, 6e, 6i, 6j,
ref. 8; 4b, 4c, 4h, 4l, 6a, ref. 5; 4e, 4f, 4g, 4j, 4m, ref. 9; 6c, ref. 7; [d] The time and the yield of the reaction by the traditonal thermal
mode at 80°C.
Scheme 1
O
R
O
R
NH 2
NH2
O
O
O
O
95% EtO H
MWI
95 % Et OH
M WI
RCHO
+
+
+
+
R CHO
N
H
N
H
6
1
1
2
3
4
5
3

Nov-Dec 2006
An Efficient One-pot Synthesis of Polyhydrobenzoacridine-1-one Derivatives
1623
irradiated for 6-19 min with power 220 W. The reaction mixture
was cooled to room temperature, then poured into water (50
mL), filtered to give the crude product, which was further
purified by recrystallization from EtOH (4a-4o). All the
products were characterized by IR, 1H NMR and elemental
analysis.
From Table 1 and Table 2, we find that microwave-
assisted reaction exhibited several advantages over
conventional heating by not only significantly reducing
the reaction time but also by improving the reaction yield
dramatically.
All the products were characterized by IR, 1H NMR and
elemental analysis. Furthermore, the structure of 6b was
established by an X-ray crystallographic analysis [13]
(Figure 1).
3,3-Dimethyl-9-(4-chlorophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4a).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3334, 2958, 1605, 1572,
1492, 1374, 1262, 1148, 1090, 1014, 851, 822, 757 cm-1; 1H nmr
(DMSO-d6): ꢀ 9.30 (s, 1H, NH), 8.46 (d, 1H, J = 8.8 Hz, ArH),
7.82 (d, 1H, J = 7.6 Hz, ArH), 7.58–7.56 (m, 1H, ArH), 7.52–
7.46 (m, 2H, ArH), 7.26-7.23 (m, 5H, ArH), 5.22 (s, 1H, CH),
2.73 (d, 1H, J = 16.0 Hz, CH), 2.66 ( d, 1H, J = 16.8 Hz, CH),
2.25 ( d, 1H, J = 16.0 Hz, CH), 2.05 ( d, 1H, J = 16.0 Hz, CH),
1.08 ( s, 3H, CH3), 0.98 ( s, 3H, CH3).
Figure 1
Anal. Calcd. for C25H22ClNO: C, 77.41; H, 5.72; N, 3.61.
Found: C, 77.52; H, 5.66; N, 3.71.
3,3-Dimethyl-9-(4-bromophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4b).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3306, 2947, 1588, 1518, 1382,
1260, 1151, 1066, 1010, 850, 806, 755 cm-1; 1H nmr (DMSO-d6):
ꢀ 9.30 (s, 1H, NH), 8.48 (d, 1H, J = 8.2 Hz, ArH), 7.83 (d, 1H, J =
7.6 Hz, ArH), 7.60–7.36 (m, 5H, ArH), 7.26-7.16 (m, 3H, ArH),
5.22(s, 1H, CH), 2.74 (d, 1H, J = 17.2 Hz, CH), 2.66 (d, 1H, J =
16.8 Hz, CH), 2.25 (d, 1H, J = 16.0 Hz, CH), 2.05 (d, 1H, J = 16.0
Hz, CH), 1.10 (s, 3H, CH3), 1.01 (s, 3H, CH3).
In conclusion, we have disclosed a facile case, using
microwave heating mode in a small amount of ethanol
without catalyst. The one-pot synthesis of hexahydro-
benzoacridine-1-one derivatives has the notable advan-
tages of wide applicability, short route and reaction
time, high yield, easy workup procedure and being
environmentally friendly.
Anal. Calcd. for C25H22BrNO: C, 69.45; H, 5.13; N, 3.24.
Found: C, 69.56; H, 5.09; N, 3.44.
3,3-Dimethyl-9-(2-chlorophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4c).
Acknowledgments.
This compound was obtained according to above general
procedure; ir (potassium bromide): 3303, 2960, 1588,
1517,1390, 1264, 1148, 1061, 1034, 802, 745, 730 cm-1; 1H nmr
(DMSO-d6): ꢀ 9.27 (s, 1H, NH), 8.47 (d, 1H, J = 8.8 Hz, ArH),
7.80 (d, 1H, J = 8.0 Hz, ArH), 7.58–7.43 (m, 3H, ArH), 7.36–
7.26 (m, 3H, ArH), 7.16-7.09 (m, 2H, ArH), 5.74 (s, 1H, CH),
2.77 (d, 1H, J = 16.0 Hz, CH), 2.69 (d, 1H, J = 16.0 Hz, CH),
2.24 (d, 1H, J = 16.0 Hz, CH), 2.02 (d, 1H, J = 16.0 Hz, CH),
1.10 (s, 3H, CH3), 1.04 (s, 3H, CH3).
We thank for the National Natural Science Foundation
of China (No. 20372057), the Nature Science Foundation
of the Jiangsu Province (No. BK2001142) and the Key
Lab of Biotechnology for Medicinal Plants of Jiangsu
Province (01AXL 14) for financial support.
EXPERIMENTAL
Anal. Calcd. for C25H22ClNO: C, 77.41; H, 5.72; N, 3.61.
Found: C, 77.66; H, 5.52; N, 3.65.
Microwave irradiation was carried out in
a modified
commercial microwave oven (2450 MHz, Nanjing Sanle)
under atmospheric pressure in a ventilating arrangement.
Melting points were determined in open capillaries and are
uncorrected. IR spectra were recorded on a TENSOR 27
spectrometer in KBr. 1H NMR spectra were measured on a
DPX 400 spectrometer operating at 400 MHz, using DMSO-d6
as solvent and TMS as internal standard. Elemental analyses
were determined by using a Perkin-Elmer 240c elemental
analysis instrument.
3,3-Dimethyl-9-(4-fluorophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4d)
This compound was obtained according to above general
procedure; ir (potassium bromide): 3318, 2957, 1678, 1589,
1518,1384, 1263, 1152, 1092, 1061, 842, 813, 752 cm-1; 1H nmr
(DMSO-d6): ꢀ 9.29 (s, 1H, NH), 8.48 (d, 1H, J = 8.4 Hz, ArH),
7.83 (d, 1H, J = 8.0 Hz, ArH), 7.58–7.56 (m, 1H, ArH), 7.48-
7.46 (m, 2H, ArH), 7.28-7.21 (m, 2H, ArH), 7.00-6.97 (m, 3H,
ArH), 5.24 (s, 1H, CH), 2.74 (d, 1H, J = 16.0 Hz, CH), 2.66 (d,
1H, J = 16.0 Hz, CH), 2.24 (d, 1H, J = 16.0 Hz, CH), 2.05 (d,
1H, J = 16.0 Hz, CH), 1.07 (s, 3H, CH3), 0.96 (s, 3H, CH3).
Anal. Calcd. for C25H22FNO: C, 80.84; H, 5.97; N, 3.77.
Found: C, 80.93; H, 5.88; N, 3.51.
General Procedure for 3,3-Dimethyl-9-substituted-1,2,3,4,9,10-
hexahydrobenzo[c]acridine-1-ones (4).
A solution of the appropriate aldehyde (2 mmol), dimedone (2
mmol), ꢀ-naphthylamine (2 mmol) and in ethanol (3 mL) was

1624
S. Tu, R. Jia, B. Jiang, Y. Zhang, J. Zhang
Vol 43
1
1517,1392, 1266, 1151, 1062, 826, 808, 762, 618 cm-1; H nmr
3,3-Dimethyl-9-(2,4-dichlorophenyl)-1,2,3,4,9,10-hexahydro-
benzo[c]acridine-1-one, (4e).
(DMSO-d6): ꢀ 9.17 (s, 1H, NH), 8.43 (d, 1H, J = 8.8 Hz, ArH),
7.78 (d, 1H, J = 8.0 Hz, ArH), 7.55 (t, 1H, J = 8.0 Hz, ArH),
7.46 (d, 1H, J = 8.0 Hz, ArH), 7.40 (d, 1H, J = 8.4 Hz, ArH),
7.29 (d, 1H, J = 8.4 Hz, ArH), 6.84 (t, 1H, J = 8.0 Hz, ArH),
6.74-6.69 (m, 2H, ArH), 5.63 (s, 1H, CH), 3.97 (s, 3H, OCH3),
3.76 (s, 3H, OCH3), 2.78(d, 1H, J = 16.0 Hz, CH), 2.68 (d, 1H, J
= 16.0 Hz, CH), 2.25 (d, 1H, J = 16.0 Hz, CH), 2.04 (d, 1H, J =
16.0 Hz, CH), 1.11 (s, 3H, CH3), 1.08 (s, 3H, CH3).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3304, 2960, 1684, 1590,
1
1518,1385, 1262, 1149, 1095, 1037, 880, 807, 754 cm-1; H nmr
(DMSO-d6): ꢀ 9.34 (s, 1H, NH), 8.47 (d, 1H, J = 8.4 Hz, ArH),
7.82 (d, 1H, J = 8.0 Hz, ArH), 7.62–7.40 (m, 4H, ArH), 7.25-7.18
(m, 3H, ArH), 5.71(s, 1H, CH), 2.78 (d, 1H, J = 16.0 Hz, CH),
2.70 (d, 1H, J = 16.0 Hz, CH), 2.25 (d, 1H, J = 16.0 Hz, CH), 2.04
(d, 1H, J = 16.0 Hz, CH), 1.10 (s, 3H, CH3), 1.05 (s, 3H, CH3).
Anal. Calcd. for C25H21Cl2NO: C, 71.10; H, 5.01; N, 3.32.
Found: C, 71.31; H, 5.11; N, 3.29.
Anal. Calcd. for C27H27NO3: C, 78.42; H, 6.58; N, 3.39.
Found: C, 78.62; H, 6.34; N, 3.51.
3,3-Dimethyl-9-(3,4-dimethoxyphenyl)-1,2,3,4,9,10-hexahydro-
benzo[c]acridine-1-one, (4j).
3,3-Dimethyl-9-(3,4-dichlorophenyl)-1,2,3,4,9,10-hexahydro-
benzo[c]acridine-1-one, (4f).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3350, 2930, 1591,
1518,1384, 1264, 1034, 767 cm-1; 1H nmr (DMSO-d6): ꢀ 9.25
(s, 1H, NH), 8.45 (d, 1H, J = 8.4 Hz, ArH), 7.82 (d, 1H, J = 8.0
Hz, ArH), 7.59-7.45 (m, 3H, ArH), 7.33 (d, 1H, J = 8.4 Hz,
ArH), 6.90 (s, 1H, ArH), 6.74-6.54 (m, 2H, ArH), 5.14 (s, 1H,
CH), 3.66 (s, 3H, OCH3), 3.63 ( s, 3H, OCH3), 2.74 (d, 1H, J =
16.8 Hz, CH), 2.66 (d, 1H, J = 17.2 Hz, CH), 2.26 (d, 1H, J =
16.0 Hz, CH), 2.06 (d, 1H, J = 16.0 Hz, CH), 1.10 (s, 3H, CH3),
1.04 (s, 3H, CH3).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3311, 2953, 1592, 1518,1390,
1262, 1151, 1060, 1029, 884, 811, 761, 633 cm-1; 1H nmr (DMSO-
d6): ꢀ 9.36 (s, 1H, NH), 8.48 (d, 1H, J = 8.4 Hz, ArH), 7.84 (d, 1H,
J = 8.0 Hz, ArH), 7.59 (t, 1H, J = 8.0 Hz, ArH), 7.54 -7.44 (m, 4H,
ArH), 7.30 (d, 1H, J = 8.0 Hz, ArH), 7.18-7.15 (m, 1H, ArH), 5.28
(s, 1H, CH), 2.76 (d, 1H, J = 16.0 Hz, CH), 2.71 (d, 1H, J = 16.0
Hz, CH), 2.26 (d, 1H, J = 16.0 Hz, CH), 2.06 (d, 1H, J = 16.0 Hz,
CH), 1.08 (s, 3H, CH3), 0.99 (s, 3H, CH3).
Anal. Calcd. for C27H27NO3: C, 78.42; H, 6.58; N, 3.39.
Found: C, 78.55; H, 6.37; N, 3.48.
Anal. Calcd. for C25H21Cl2NO: C, 71.10; H, 5.01; N, 3.32.
Found: C, 71.25; H, 5.09; N, 3.18.
3,3-Dimethyl-9-(4-hydroxy-3-methoxyphenyl)-1,2,3,4,9,10-hexa-
hydrobenzo[c]acridine-1-one, (4k).
3,3-Dimethyl-9-(3,4-methylenedioxylphenyl)-1,2,3,4,9,10-hexa–
hydrobenzo[c]acridine-1-one, (4g).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3289, 2960, 1567, 1496,
1394, 1262, 1062, 1092, 873, 810, 773, 644 cm-1; 1H nmr
(DMSO-d6): ꢀ 9.25 (s, 1H, NH), 8.64 (s, 1H, OH), 8.44 (d, 1H, J
= 8.8 Hz, ArH), 7.82 (d, 1H, J = 8.4 Hz, ArH), 7.57-7.45 (m,
3H, ArH), 7.32 (d, 1H, J = 8.4 Hz, ArH), 6.85 (s, 1H, ArH), 6.55
(s, 2H, ArH), 5.09 (s, 1H, CH), 3.67 (s, 3H, OCH3), 2.73(d, 1H,
J = 16.0 Hz, CH), 2.65 (d, 1H, J = 16.0 Hz, CH), 2.25 (d, 1H, J =
16.0 Hz, CH), 2.05 (d, 1H, J = 16.0 Hz, CH), 1.09 (s, 3H,
CH3),1.04 (s, 3H, CH3).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3329, 2956, 1585, 1518,1392,
1230, 1151, 1038, 1030, 883, 814, 765, 640 cm-1; 1H nmr (DMSO-
d6): ꢀ 9.25 (s, 1H, NH), 8.46 (d, 1H, J = 8.4 Hz, ArH), 7.83 (d, 1H,
J = 8.0 Hz, ArH), 7.59-7.46 (m, 3H, ArH), 7.29 (d, 1H, J = 8.8 Hz,
ArH), 6. 76-6. 64 (m, 3H, ArH), 5.88 (d, 2H, J = 10.8 Hz, CH),
5.13(s, 1H, CH), 2.74 (d, 1H, J = 17.2 Hz, CH), 2.65 (d, 1H, J =
17.2 Hz, CH),2.24 (d, 1H, J = 16.0 Hz, CH), 2.06 (d, 1H, J = 16.0
Hz, CH), 1.08 (s, 3H, CH3), 1.01 (s, 3H, CH3).
Anal. Calcd. for C26H23NO3: C, 78.57; H, 5.83; N, 3.52.
Found: C, 78.34; H, 5.98; N, 3.48.
Anal. Calcd. for C26H25NO3: C, 78.17; H, 6.31; N, 3.51.
Found: C, 78.27; H, 6.14; N, 3.37.
3,3-Dimethyl-9-(4-methoxyphenyl)-1,2,3,4,9,10-hexahydro-
benzo[c]acridine-1-one, (4h).
3,3-Dimethyl-9-(4-nitrophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4l).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3350, 2954, 1591, 1496,
1384, 1254, 1149, 1384, 1254, 1149, 1036, 831, 807, 765, 646
This compound was obtained according to above general
procedure; ir (potassium bromide): 3326, 2960, 1594, 1497,
1395, 1262, 1150, 1060, 834, 804, 756, 640 cm-1; 1H nmr
(DMSO-d6): ꢀ 9.40 (s, 1H, NH), 8.51 (d, 1H, J = 8.8 Hz, ArH),
8.09 (d, 2H, J = 8.4 Hz, ArH), 7.84 (d, 1H, J = 8.0 Hz, ArH),
7.62-7.48 (m, 5H, ArH), 7.27 (d, 1H, J = 8.4 Hz, ArH), 5.41(s,
1H, CH)，2.76 (d, 1H, J = 16.8 Hz, CH), 2.69 (d, 1H, J = 16.8
Hz, CH), 2.26 (d, 1H, J = 16.4 Hz, CH), 2.05 (d, 1H, J = 16.4
Hz, CH), 1.09 (s, 3H, CH3), 0.98 (s, 3H, CH3).
1
cm-1; H nmr (DMSO-d6): ꢀ 9.23 (s, 1H, NH), 8.46 (d, 1H, J =
8.8 Hz, ArH), 7.82 (d, 1H, J = 8.0 Hz, ArH), 7.59-7.44 (m, 3H,
ArH), 7.25 (d, 1H, J = 8.4 Hz, ArH), 7.12 (d, 2H, J = 8.4 Hz,
ArH), 6.73 (d, 2H, J = 8.4 Hz, ArH), 5.14 (s, 1H, CH), 3.64 (s,
3H, OCH3), 2.73 (d, 1H, J = 16.8 Hz, CH), 2.65 (d, 1H, J = 16.8
Hz, CH), 2.24 (d, 1H, J = 16.0 Hz, CH), 2.04 (d, 1H, J = 16.0
Hz, CH), 1.08 (s, 3H, CH3),1.00 (s, 3H, CH3).
Anal. Calcd. for C25H22N2O3: C, 75.36; H, 5.57; N, 7.03.
Found: C, 75.66; H, 5.33; N, 7.21.
Anal. Calcd. for C26H25NO2: C, 81.43; H, 6.57; N, 3.65.
Found: C, 81.55; H, 6.34; N, 3.59.
3,3-Dimethyl-9-(3-nitrophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4m).
3,3-Dimethyl-9-(2,3-dimethoxyphenyl)-1,2,3,4,9,10-hexahydro–
benzo[c]acridine-1-one, (4i).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3310, 2956, 1589, 1387,
1262, 1150, 1093, 831, 807, 758, 611 cm-1; 1H nmr (DMSO-d6):
This compound was obtained according to above general
procedure; ir (potassium bromide): 3314, 2951, 1588,

Nov-Dec 2006
An Efficient One-pot Synthesis of Polyhydrobenzoacridine-1-one Derivatives
1625
ꢀ 9.43 (s, 1H, NH), 8.50 (d, 1H, J = 8.4 Hz, ArH), 8.08 (s, 1H,
ArH), 7.97-7.95 (dd, 1H, J1 = 8.4 Hz, J2 = 1.4 Hz, ArH), 7.74 (d,
1H, J = 7.6 Hz, ArH), 7.72 (d, 1H, J = 7.8 Hz, ArH), 7.61-7.49
(m, 4H, ArH), 7.34 (d, 1H, J = 8.4 Hz, ArH), 5.44 (s, 1H,
CH) 2.78 (d, 1H, J = 15.6 Hz, CH), 2.74 (d, 1H, J = 15.6 Hz,
CH), 2.27 (d, 1H, J = 16.4 Hz, CH), 2.05 (d, 1H, J = 16.0 Hz,
CH), 1.09 (s, 3H, CH3), 0.99 (s, 3H, CH3).
Anal. Calcd. for C25H22ClNO: C, 77.41; H, 5.72; N, 3.61.
Found: C, 77.65; H, 5.81; N, 3.44.
3,3-Dimethyl-9-(4-bromophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[a]acridine-1-one, (6b).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3264, 2927, 1595, 1520,
1493, 1382, 1238, 1146, 1073, 1101, 835, 807, 711, 650 cm-1; 1H
nmr (DMSO-d6): ꢀ 9.76 (s, 1H, NH), 7.90 (d, 1H, J = 8.4 Hz,
ArH), 7.82-7.79 (m, 2H, ArH), 7.42 (t, 1H, J = 7.6 Hz, ArH),
7.34-7.31 (m, 4H, ArH), 7.18 (d, 2H, J = 8.4 Hz, ArH), 5.78 (s,
1H, CH), 2.56 (d, 1H, J = 16.8 Hz, CH), 2.39 (d, 1H, J = 16.8
Hz, CH), 2.23 (d, 1H, J = 16.4 Hz, CH), 2.03 (d, 1H, J = 16.4
Hz, CH), 1.04 (s, 3H, CH3), 0.84 (s, 3H, CH3).
Anal. Calcd. for C25H22N2O3: C, 75.36; H, 5.57; N, 7.03.
Found: C, 75.56; H, 5.36; N, 7.15.
3,3-Dimethyl-9-(2-thiophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[c]acridine-1-one, (4n).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3320, 2957, 1585, 1518,
1
1495, 1377, 1260, 1149, 1060, 887, 851, 747, 697 cm-1; H nmr
Anal. Calcd. for C25H22BrNO: C, 69.45; H, 5.13; N, 3.24.
Found: C, 69.66; H, 5.24; N, 3.09.
(DMSO-d6): ꢀ 9.42 (s, 1H, NH), 8.44 (d, 1H, J = 8.8 Hz, ArH),
7.89 (d, 1H, J = 8.4 Hz, ArH), 7.56-7.44 (m, 2H, ArH), 7.35 (d,
1H, J = 5.2 Hz, ArH), 7.24 (s, 1H, ArH), 7.14 (d, 1H, J = 5.2 Hz,
ArH), 6.95 (t, 1H, J = 4 Hz, ArH), 6.78-6.76 (m, 1H, ArH), 5.24
(s, 1H, CH) 2.73 (d, 1H, J = 16.8 Hz, CH), 2.62 (d, 1H, J =
16.8 Hz, CH), 2.23 (d, 1H, J = 16.4 Hz, CH), 2.13 (d, 1H, J =
16.4 Hz, CH), 0.97 (s, 3H, CH3), 0.88 (s, 3H, CH3).
3,3-Dimethyl-9-(4-methoxyphenyl)-1,2,3,4,9,10-hexahydrobenzo-
[a]acridine-1-one, (6c).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3269, 2928, 1599, 1520,
1499, 1383, 1259, 1175, 1148, 1033, 811, 746, 678 cm-1; 1H nmr
(DMSO-d6): ꢀ 9.67 (s, 1H, NH), 7.94 (d, 1H, J = 8.8 Hz, ArH),
7.78 (t, 2H, J = 9.8 Hz, ArH), 7.41 (t, 1H, J = 7.6 Hz, ArH),
7.32-7.28 (m, 2H, ArH), 7.13 (d, 2H, J = 8.4 Hz, ArH), 6.68 (d,
2H, J = 8.8 Hz, ArH), 5.73 (s, 1H, CH), 3.61 (s, 3H, OCH3),
2.54 (d, 1H, J = 16.4 Hz, CH), 2.38 (d, 1H, J = 16.4 Hz, CH),
2.22 (d, 1H, J = 16.0 Hz, CH), 2.02 (d, 1H, J = 16.0 Hz, CH),
1.03 (s, 3H, CH3), 0.86 (s, 3H, CH3).
Anal. Calcd. for C23H21NOS: C, 76.85; H, 5.89; N, 3.90; S,
8.92. Found: C, 76.67; H, 5.98; N, 3.78; S, 8.99.
3,3-Dimethyl-9-(n-butyl)-1,2,3,4,9,10-hexahydrobenzo[c]acri-
dine-1-one, (4o).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3321, 2953, 1586, 1519,
1495, 1399, 1262, 1151, 1041, 816, 747, 661, 618, 595 cm-1; 1H
nmr (DMSO-d6): ꢀ 9.03 (s, 1H, NH), 8.40 (d, 1H, J = 8.0 Hz,
ArH), 7.86 (d, 1H, J = 8.4 Hz, ArH), 7.55-7.49 (m, 3H, ArH),
7.28 (d, 1H, J = 8.4 Hz, ArH), 4.08 (t, 1H, J = 2.7 Hz, CH), 2.65
(d, 1H, J = 24.2 Hz, CH), 2.54 (d, 1H, J = 24.2 Hz, CH), 2.24 (d,
1H, J = 16.0 Hz, CH), 2.12 (d, 1H, J = 15.6 Hz, CH), 1.60-1.50
(m, 2H, CH), 1.40-1.30 (m, 2H, CH), 1.10 (s, 3H, CH3), 1.08 (s,
3H, CH3), 1.00-0.98 (m, 2H, CH), 0.72 (t, 3H, J = 3.5 Hz, CH3).
Anal. Calcd. for C23H27NO: C, 82.84; H, 8.16; N, 4.20. Found:
C, 82.66; H, 8.36; N, 4.33.
Anal. Calcd. for C26H25NO2: C, 81.43; H, 6.57; N, 3.65.
Found: C, 81.66; H, 6.34; N, 3.54.
3,3-dimethyl-9-(3,4-methylenedioxylphenyl)-1,2,3,4,9,10-hexa-
hydrobenzo[a]acridine-1-one, (6d).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3264, 2958, 1583, 1521,
1497, 1431, 1397, 1240, 1148, 1038, 918, 812, 749, 670, 634
1
cm-1; H nmr (DMSO-d6): ꢀ 9.70 (s, 1H, NH), 7.95 (d, 1H, J =
8.4 Hz, ArH), 7.79 (t, 2H, J = 8.8 Hz, ArH), 7. 43 (t, 1H, J = 7.6
Hz, ArH), 7.32 (t, 2H, J = 8.0 Hz, ArH), 6. 78 (s, 1H, ArH),
6.67-6.62 (m, 2H, ArH), 5.86 (d, 2H, J = 14.4 Hz, CH), 5.73 (s,
1H, CH), 2.54 (d, 1H, J = 16.8 Hz, CH), 2.40 (d, 1H, J = 16.8
Hz, CH), 2.22 (d, 1H, J = 16.0 Hz, CH), 2.04 (d, 1H, J = 16.0
Hz, CH), 1.04 (s, 3H, CH3), 0.88 (s, 3H, CH3).
General Procedure for 3,3-Dimethyl-9-substituted-1,2,3,4,9,10-
hexahydrobenzo[a]acridine-1-ones (6).
A solution of the appropriate aldehyde (2 mmol), dimedone (2
mmol), β-naphthylamine (2 mmol) and in ethanol (3 mL) was
irradiated for 4-9 min with power 220 W. The reaction mixture
was cooled to room temperature, then poured into water (50
mL), filtered to give the crude product, which was further
purified by recrystallization from EtOH (6a-6m). All products
were characterized by IR, 1H NMR and elemental analysis.
Anal Calcd. for C26H23NO3: C, 78.57; H, 5.83; N, 3.52. Found:
C, 78.66; H, 5.68; N, 3.32.
3,3-Dimethyl-9-(3,4-dimethoxyphenyl)-1,2,3,4,9,10-hexahydro-
benzo[a]acridine-1-one, (6e).
3,3-Dimethyl-9-(4-chlorophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[a]acridine-1-one, (6a).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3294, 2899, 1602, 1513,
1493, 1417, 1339, 1234, 1137, 1029, 980, 936, 809, 748, 648
This compound was obtained according to above general
procedure; ir (potassium bromide): 3257, 2935, 1579, 1520,
1493, 1387, 1258, 1150, 1086, 1013, 843, 820, 748, 659 cm-1; 1H
nmr (DMSO-d6): ꢀ 9.77 (s, 1H, NH), 7.90 (d, 1H, J=8.8 Hz,
ArH), 7.82-7.79 (m, 2H, ArH), 7.42 (t, 1H, J=7.6 Hz, ArH),
7.33–7.30 (m, 2H, ArH), 7.24 (d, 2H, J=8.4 Hz, ArH), 7.19 (d,
2H, J=8.4 Hz, ArH), 5.80 (s, 1H, CH), 2.56 (d, 1H, J=16.8 Hz,
CH), 2.39 ( d, 1H, J=16.8 Hz, CH), 2.23 ( d, 1H, J=16.0 Hz,
CH), 2.03 ( d, 1H, J=16.0 Hz, CH), 1.04 ( s, 3H, CH3), 0.84 ( s,
3H, CH3).
1
cm-1; H nmr (DMSO-d6): ꢀ 9.68 (s, 1H, NH), 8.00 (d, 1H, J =
8.4 Hz, ArH), 7.81-7.76 (m, 2H, ArH), 7.43 (t, 1H, J = 7.6 Hz,
ArH), 7.31 (t, 2H, J = 7.0 Hz, ArH), 6.96 (s, 1H, ArH), 6.67 (d,
1H, J = 8.4 Hz, ArH), 6.58 (dd, 1H, J1 = 8.2 Hz, J2 = 1.6 Hz,
ArH), 5.74 (s, 1H, CH), 3.63 (s, 3H, OCH3), 3.60 ( s, 3H,
OCH3), 2.55 (d, 1H, J = 16.8 Hz, CH), 2.39 (d, 1H, J = 16.8 Hz,
CH), 2.23 (d, 1H, J = 16.0 Hz, CH), 2.05 (d, 1H, J = 16.0 Hz,
CH), 1.06 (s, 3H, CH3), 0.88 (s, 3H, CH3).

1626
S. Tu, R. Jia, B. Jiang, Y. Zhang, J. Zhang
Vol 43
3,3-Dimethyl-9-(2-thiophenyl)-1,2,3,4,9,10-hexahydrobenzo[a]-
acridine-1-one, (6j).
Anal. Calcd. for C27H27NO3: C, 78.42; H, 6.58; N, 3.39.
Found: C, 78.56; H, 6.32; N, 3.16.
This compound was obtained according to above general
procedure; ir (potassium bromide): 3266, 2927, 1600, 1521,
3,3-Dimethyl-9-(phenyl)-1,2,3,4,9,10-hexahydrobenzo[a]acri-
dine-1-one, (6f).
1
1493, 1379, 1235, 1184, 1032, 978, 812, 746, 693 cm-1; H nmr
This compound was obtained according to above general
procedure; ir (potassium bromide): 3236, 2961, 1579, 1520,
1494, 1385, 1261, 1119, 1035, 982, 839, 816, 752, 698, 657
(DMSO-d6): ꢀ 9.83 (s, 1H, NH), 8.00 (d, 1H, J = 8.8 Hz, ArH),
7.85-7.80 (m, 2H, ArH), 7.49 (t, 1H, J = 7.6 Hz, ArH), 7.38-7.28
(m, 2H, ArH), 7.11 (d, 1H, J = 4.8 Hz, ArH), 6.72 (t, 1H, J = 4.4
Hz, ArH), 6.60 (d, 1H, J = 3.2 Hz, ArH), 6.12 (s, 1H, CH), 2.56
(d, 1H, J = 16.8 Hz, CH), 2.41 (d, 1H, J = 16.8 Hz, CH), 2.27 (d,
1H, J = 16.0 Hz, CH), 2.11 (d, 1H, J = 16.0 Hz, CH), 1.06 (s,
3H, CH3), 0.95 (s, 3H, CH3).
1
cm-1; H nmr (DMSO-d6): ꢀ 9.71 (s, 1H, NH), 7.95 (d, 1H, J =
8.4 Hz, ArH), 7.79 (t, 2H, J = 7.6 Hz, ArH), 7.42 (t, 1H, J = 7.6
Hz, ArH), 7.33-7.23 (m, 3H, ArH), 7.12 (t, 2H, J = 7.6 Hz,
ArH), 6.99 (t, 2H, J = 7.2 Hz, ArH), 5.79 (s, 1H, CH), 2.55 (d,
1H, J = 16.8 Hz, CH), 2.40 (d, 1H, J = 16.8 Hz, CH), 2.22 (d,
1H, J = 16.0 Hz, CH), 2.02 (d, 1H, J = 16.0 Hz, CH), 1.03 (s,
3H, CH3), 0.84 (s, 3H, CH3).
Anal. Calcd. for C23H21NOS: C, 76.85; H, 5.89; N, 3.90; S,
8.92. Found: C, 76.67; H, 5.76; N, 3.79; S, 8.67.
Anal. Calcd. for C25H23NO: C, 84.95; H, 6.56; N, 3.96. Found:
C, 84.81; H, 6.77; N, 3.73.
3,3-Dimethyl-9-[4-(1,3-benzoxazol-2-yl)phenyl]-1,2,3,4,9,10-
hexahydrobenzo[a]acridine-1-one, (6k).
3,3-Dimethyl-9-(4-nitrophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[a]acridine-1-one, (6g).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3261, 2954, 1601, 1523,
1499, 1471, 1399, 1243, 1170, 1149, 1016, 816, 745, 660 cm-1;
1H nmr (DMSO-d6): ꢀ 9.84 (s, 1H, NH), 8.01-7.95 (m, 3H,
ArH), 7.84-7.73 (m, 4H, ArH), 7.49-7.32 (m, 7H, ArH), 5.91 (s,
1H, CH), 2.59 (d, 1H, J = 16.8 Hz, CH), 2.43 (d, 1H, J = 16.8
Hz, CH), 2.25 (d, 1H, J = 16.0 Hz, CH), 2.07 (d, 1H, J = 16.0
Hz, CH), 1.05 (s, 3H, CH3), 0.85 (s, 3H, CH3).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3269, 2959, 1602, 1520,
1
1493, 1383, 1344, 1110, 1014,831, 815, 746, 696 cm-1; H nmr
(DMSO-d6): ꢀ 9.88 (s, 1H, NH), 8.04 (d, 2H, J = 8.8 Hz, ArH),
7.91-7.82 (m, 3H, ArH), 7.51 (d, 2H, J = 8.8 Hz, ArH), 7.44-
7.31 (m, 3H, ArH), 5.95 (s, 1H, CH)ꢀ2.58 (d, 1H, J = 16.8 Hz,
CH), 2.41 (d, 1H, J = 16.8 Hz, CH), 2.25 (d, 1H, J = 16.0 Hz,
CH), 2.03 (d, 1H, J = 16.0 Hz, CH), 1.04 (s, 3H, CH3), 0.82 (s,
3H, CH3)
Anal. Calcd. for C32H26N2O2: C, 81.68; H, 5.57; N, 5.95.
Found: C, 81.85; H, 5.78; N, 5.89.
3,3-Dimethyl-9-(1H-indol-3-yl)-1,2,3,4,9,10-hexahydrobenzo-
[a]acridine-1-one, (6l).
Anal. Calcd. for C25H22N2O3: C, 75.36; H, 5.57; N, 7.03.
Found: C, 75.57; H, 5.74; N, 7.13.
This compound was obtained according to above general
procedure; ir (potassium bromide): 3268, 2924, 1569, 1519,
1500, 1467, 1351, 1240, 1154, 1093, 1031, 813, 732, 656 cm-1;
1H nmr (DMSO-d6): ꢀ 10.65 (s, 1H, NH), 9.77 (s, 1H, NH), 8.12
(d, 1H, J = 8.4 Hz, ArH), 7.73 (t, 2H, J = 9.2 Hz, ArH), 7.54 (d,
1H, J = 7.6 Hz, ArH), 7.38-7.08 (m, 5H, ArH), 6.90 (t, 1H, J =
7.6 Hz, ArH), 6.80 (t, 1H, J = 7.6 Hz, ArH), 6.08 (s, 1H, CH),
2.54 (d, 1H, J = 16.4 Hz, CH), 2.40 (d, 1H, J = 16.4 Hz, CH),
2.19 (d, 1H, J = 16.0 Hz, CH), 1.98 (d, 1H, J = 16.0 Hz, CH),
1.02 (s, 3H, CH3), 0.77 (s, 3H, CH3).
3,3-Dimethyl-9-(3-nitrophenyl)-1,2,3,4,9,10-hexahydrobenzo-
[a]acridine-1-one, (6h).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3260, 2928, 1582, 1522,
1494, 1385, 1234, 1155, 1093, 982, 923, 811, 729, 687, 654
cm-1; 1H nmr (DMSO-d6): ꢀ 9.90 (s, 1H, NH), 8.07 (s, 1H, ArH),
7.96-7.82 (m, 4H, ArH), 7.70 (d, 1H, J = 7.6 Hz, ArH), 7.48-
7.31 (m, 4H, ArH), 5.97 (s, 1H, CH)ꢀ2.58 (d, 1H, J = 16.4 Hz,
CH), 2.43 (d, 1H, J = 16.4 Hz, CH), 2.25 (d, 1H, J = 16.0 Hz,
CH), 2.04 (d, 1H, J = 16.0 Hz, CH), 1.06 (s, 3H, CH3), 0.82 (s,
3H, CH3).
Anal. Calcd. for C27H24N2O: C, 82.62; H, 6.16; N, 7.14.
Found: C, 82.88; H, 6.09; N, 7.21.
Anal. Calcd. for C25H22N2O3: C, 75.36; H, 5.57; N, 7.03.
Found: C, 75.57; H, 5.73; N, 7.17.
3,3-Dimethyl-9-(n-butyl)-1,2,3,4,9,10-hexahydrobenzo[a]acri–
dine-1-one, (6m).
3,3-Dimethyl-9-(4-hydroxy-3-methoxyphenyl)-1,2,3,4,9,10-hexa-
hydrobenzo[a]acridine-1-one, (6i).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3280, 2952, 1596, 1521,
1
This compound was obtained according to above general
procedure; ir (potassium bromide): 3267, 2958, 1602, 1511,
1497, 1427, 1399, 1272, 1149, 1034, 979, 857, 748, 630 cm-1; 1H
nmr (DMSO-d6): ꢀ 9.64 (s, 1H, NH), 8.61 (s, 1H, OH), 8.00 (d,
1H, J = 8.4 Hz, ArH), 7.81-7.75 (m, 2H, ArH), 7.43 (t, 1H, J =
7.6 Hz, ArH), 7.33-7.28 (m, 2H, ArH), 6.92 (s, 1H, ArH), 6.47
(t, 2H, J = 9.6 Hz, ArH), 5.70 (s, 1H, CH), 3.64 (s, 3H, OCH3),
2.55(d, 1H, J = 16.4 Hz, CH), 2.38 (d, 1H, J = 16.4 Hz, CH),
2.22 (d, 1H, J = 16.0 Hz, CH), 2.04 (d, 1H, J = 16.0 Hz, CH),
1.06 (s, 3H, CH3), 0.88 (s, 3H, CH3).
1491, 1399, 1262, 1151, 1128, 818, 749, 709, 661 cm-1; H
nmr (DMSO-d6): ꢀ 9.40 (s, 1H, NH), 7.98 (d, 1H, J=8.4 Hz,
ArH), 7.82 (d, 1H, J=8.0 Hz, ArH), 7.71 (d, 1H, J=8.8 Hz,
ArH), 7.51 (t, 1H, J=7.6 Hz, ArH), 7.35 (t, 1H, J=7.6 Hz,
ArH), 7.18 (d, 1H, J=8.8 Hz, ArH), 4.78 (t, 1H, J= 4.8 Hz,
CH), 2.50 (d, 1H, J=16.8 Hz, CH), 2.39 (d, 1H, J=16.8 Hz,
CH), 2.23 (d, 1H, J=16.0 Hz, CH), 2.15 (d, 1H, J=16.0 Hz,
CH), 1.53-1.43 (m, 2H, CH), 1.24-1.14 (m, 2H, CH), 1.11
(s, 3H, CH3), 1.07 (s, 3H, CH3), 0.99-0.90 (m, 2H, CH),
0.68 (t, 3H, J= 7.2 Hz, CH3).
Anal. Calcd. for C26H25NO3: C, 78.17; H, 6.31; N, 3.51.
Found: C, 78.35; H, 6.55; N, 3.24.
Anal. Calcd. for C23H27NO: C, 82.84; H, 8.16; N, 4.20. Found:
C, 82.99; H, 8.23; N, 4.31.

Nov-Dec 2006
An Efficient One-pot Synthesis of Polyhydrobenzoacridine-1-one Derivatives
1627
REFERENCES AND NOTES
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diffractometer. Crystal data for 6b: C25H22BrNO, yellow, crystal
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7.296(4), b = 9.597(5), c = 15.304(8) Å, ꢀ = 94.038(7)°, ꢁ =
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2, Dc = 1.385 g/cm3, ꢀ = 0.71073 Å, μ (Mokꢁ) = 1.997 mm-1,
F(000) = 444, S =1.008, R1= 0.0442, wR2 = 0.0999.
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