Facile and highly efficient procedure for the synthesis of triazolyl methoxyphenyl 1,8-dioxo-decahydroacridines via one-pot, pseudo-five-component reaction

Article abstract of DOI:10.1080/00397911.2011.577263

A series of triazolyl methoxyphenyl 1,8-dioxo-decahydroacridine derivatives has been prepared in a one-pot, pseudo-five-component reaction of aromatic propargylated aldehydes, various azides, dimedone, and a variety of amines in the presence of Cu(OAc)2/sodium ascorbate and 1-methylimidazolium trifluoroacetate ([Hmim]TFA) as the catalyst in good yields.

Full text of DOI:10.1080/00397911.2011.577263

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Facile and Highly Efficient Procedure for
the Synthesis of Triazolyl Methoxyphenyl
1,8-Dioxo-decahydroacridines via One-
Pot, Pseudo-Five-Component Reaction
Minoo Dabiri a , Peyman Salehi b , Mahboobeh Bahramnejad a ,
Fatemeh Sherafat a & Morteza Bararjanian a
a Department of Chemistry, Faculty of Science , Shahid Beheshti
University , Tehran , Iran
b Department of Phytochemistry, Medicinal Plants and Drugs
Research Institute , Shahid Beheshti University , Tehran , Iran
Accepted author version posted online: 10 Jan 2012.Published
online: 17 Aug 2012.
To cite this article: Minoo Dabiri , Peyman Salehi , Mahboobeh Bahramnejad , Fatemeh Sherafat
& Morteza Bararjanian (2012) Facile and Highly Efficient Procedure for the Synthesis of Triazolyl
Methoxyphenyl 1,8-Dioxo-decahydroacridines via One-Pot, Pseudo-Five-Component Reaction,
Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic
Chemistry, 42:21, 3117-3127, DOI: 10.1080/00397911.2011.577263
To link to this article: http://dx.doi.org/10.1080/00397911.2011.577263
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Synthetic Communications1, 42: 3117–3127, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2011.577263
FACILE AND HIGHLY EFFICIENT PROCEDURE FOR THE
SYNTHESIS OF TRIAZOLYL METHOXYPHENYL
1,8-DIOXO-DECAHYDROACRIDINES VIA ONE-POT,
PSEUDO-FIVE-COMPONENT REACTION
Minoo Dabiri,1 Peyman Salehi,2 Mahboobeh Bahramnejad,1
Fatemeh Sherafat,1 and Morteza Bararjanian1
1Department of Chemistry, Faculty of Science, Shahid Beheshti University,
Tehran, Iran
2Department of Phytochemistry, Medicinal Plants and Drugs Research
Institute, Shahid Beheshti University, Tehran, Iran
GRAPHICAL ABSTRACT
Abstract A series of triazolyl methoxyphenyl 1,8-dioxo-decahydroacridine derivatives has
been prepared in a one-pot, pseudo-five-component reaction of aromatic propargylated alde-
hydes, various azides, dimedone, and a variety of amines in the presence of Cu(OAc)2/
sodium ascorbate and 1-methylimidazolium trifluoroacetate ([Hmim]TFA) as the catalyst
in good yields.
Keywords Click multicomponent; decahydroacridine; one-pot reaction; pseudo-five-
component reaction; triazole
INTRODUCTION
‘‘Click chemistry’’[1] has recently become a popular method in organic and
biological chemistry. This powerful strategy relies mainly upon the construction of
carbon–heteroatom bonds using spring-loaded reactants. Its applications are found
in nearly all areas of modern chemistry from drug discovery to material science.[2]
The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal
alkynes has become a gold standard in click chemistry because of its reliability, speci-
ficity, and biocompatibility of the product.[3–5] Acridine derivatives have been known
[7]
since the 19th century[6] to play particular roles in biocatalysis
and organic
Received March 14, 2011.
Address correspondence to either Minoo Dabiri, Department of Chemistry, or Peyman Salehi,
Department of Phytochemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran.
E-mail: m-dabiri@sbu.ac.ir; p-salehi@sbu.ac.ir
3117

3118
M. DABIRI ET AL.
chemistry.[8] The acridine moiety possesses a wide range of biological activities
including antimalarial,[9] antitumor,[10] antiprion,[11] anti-Alzheimer,[12] antileishma-
nial, and antitrypanosomal[13] activities, and there are various methods available for
the synthesis of acridine derivatives.[14–16]
In our continued interest in the development of highly expedient methodolo-
gies[17] for the synthesis of fine chemicals and heterocyclic compounds of biological
importance, and according to our experience in multicomponent reactions and click
chemistry,[18] we report here a powerful and reliable procedure for the synthesis of
triazolyl methoxyphenyl 1,8-dioxo-decahydroacridines through a one-pot, pseudo-
five-component reaction.
RESULTS AND DISCUSSION
For construction of the target acridine derivatives, we designed a pseudo-five-
component reaction of aromatic propargylated aldehydes 1a–d with various azides
2a–f, amines 3a–d, and dimedone 4 in the presence of catalytic amounts of
Cu(OAc)2, sodium ascorbate, and an acidic catalyst (Scheme 1).
To determine the optimum conditions for the reaction, we studied the conden-
sation reaction under a variety of conditions. Accordingly, in our initial research, the
treatment of propargylated aldehyde 1a with 4-nitrophenyl azide 2a, 3-nitroaniline
3b, and dimedone 4 in the presence of catalytic amounts of Cu(OAc)2 (10 mol%)
and sodium ascorbate (20% mol) in the mixture of H2O= EtOH (1=1, v=v, 5 mL)
was studied in the presence of different acidic catalysts and heating conditions. After
preliminary screening of different conditions, it was found that in the absence of the
acidic catalyst (Table 1, entries 1 and 2), compound 6 was isolated in good yield
(90%) instead of the desired product 5a. Therefore, it was concluded that the pres-
ence of the acidic catalyst has a vital role in formation of the final product 5a. Thus,
we examined the influence of several acidic catalysts at different temperatures
(Table 1, entries 3–10). As can be seen, the best result was obtained with 10 mol%
of [Hmim]TFA at 100 ꢀC (Table 1, entry 10).
After optimizing the conditions, the scope of this four-component reaction was
examined by using other aromatic propargylated aldehydes 1a–d, azides 2a–e,
amines 3a–d, and dimedone 4 in the presence of catalytic amounts of Cu(OAc)2
Scheme 1. One-pot, pseudo-five-component synthesis of triazolyl methoxyphenyl 1,8-dioxo-decahydro-
acridines 5a–n.

TRIAZOLYL METHOXYPHENYL 1,8-DIOXO-DECAHYDROACRIDINES
3119
Table 1. Optimization of the reaction conditiona,b
Entry
Catalystc
Temp.(ꢀC)
Yield of 5a (%)d
Time (h)
e
e
1
2
—
—
25
80
Tracef
Tracef
Trace
Trace
40
12
12
12
12
12
12
12
12
12
6
3
p-TsOH
p-TsOH
p-TsOH
25
80
4
5
100
25
6
Silica sulfuric acid
Silica sulfuric acid
IL ([Hmim]TFA)
IL ([Hmim]TFA)
IL ([Hmim]TFA)
Trace
Trace
43
7
100
25
8
9
10
80
100
65
93
aReaction conditions: propargylated aldehyde 1a (1 mmol), 4-nitrophenyl azide 2a (1 mmol), 3-nitroanil-
ine 3b (1.2 mmol), and dimedone 4 (2 mmol).
bIn all reactions the conditions were optimized for a 100% conversion.
cThe reactions were run in the presence of 10 mol% of catalyst.
dIsolated yield based on 1a.
eThe reaction was run under neat conditions.
fOnly compound 6 was isolated.
(10 mol%), sodium ascorbate (20% mol), and [Hmim]TFA (10 mol%) at 100 ꢀC for
6 h. The results are summarized in Table 2. Generally, as indicated in Table 2, differ-
ent types of functional groups such as nitro and chloro were tolerated on aromatic
azides (Table 2, entries 1–9 and 12). Also benzyl azides were reacted suitably in all
reactions (Tables 2, entries 10, 11, 13, and 14). Ammonium acetate as well as aro-
matic amines underwent the conversion and afforded the products with good yields
(Tables 2, entries 10 and 13).
The most probable mechanism of this sequential reaction, which is exhibited in
Scheme 2, includes initial formation of intermediate 6 by a click reaction of the aro-
matic propargylated aldehydes 1 and azides 2 in the presence of catalytic amounts of
Cu(OAc)2 (10 mol%) and sodium ascorbate (20% mol) in H2O=EtOH as solvent.
Then, it involves a fast Knoevenagel condensation between 1,2,3-triazolyl methoxy
benzaldehyde 6 and dimedone 4 in the presence of acidic ionic liquid followed by
a Michael addition of the second molecule of dimedone to the unsaturated ketone
8. Finally, nucleophilic addition of amines to compound 9, followed by cyclization
and dehydration, furnishes the desired product 5.

3120
M. DABIRI ET AL.
Table 2. Synthesis of triazolyl methoxyphenyl 1,8-dioxo-decahydroacridines 5a–n
Entry
Aldehyde
Azide
Amine
Product
Yield (%)a
Mp (ꢀC)
1
2
1a
1a
1b
1a
1a
1a
1b
1a
1c
1d
1d
1d
1d
1d
2a
2a
2a
2a
2b
2b
2a
2e
2a
2c
2d
2a
2d
2d
3b
3c
3b
3a
3b
3a
3b
3a
3a
3d
3a
3b
3d
3b
5a
5b
5c
5d
5e
5f
93
83
86
74
92
85
84
85
82
75
87
93
78
91
289–291
266–267
114–116
268–270
240–242
275–276
266–268
276–278
272–273
135–138
238–240
274–275
128–130
258–259
3
4
5
6
7
5g
5h
5i
8
9
10
11
12
13
14
5j
5k
5l
5m
5n
aIsolated yield.
Scheme 2. Plausible mechanism of the reaction.

TRIAZOLYL METHOXYPHENYL 1,8-DIOXO-DECAHYDROACRIDINES
3121
CONCLUSION
In summary, a very simple and efficient synthesis of triazolyl methoxyphenyl
1,8-dioxo-decahydroacridines has been achieved via sequential click–Knoevenagel
condensation–Michael addition–cyclocondensation reaction. Several derivatives of
the title compounds with a variety of substituents were synthesized to show the
diversity of the method. We believe that this method could be used for the combina-
torial synthesis of triazolyl methoxyphenyl 1,8-dioxo-decahydroacridines 5a–n in
drug discovery programs. The salient features of this method include high conver-
sions, short reaction times, cleaner reaction profiles, high bond-forming efficiency
(BFE), and the use of inexpensive and readily available starting materials.
EXPERIMENTAL
All starting materials were obtained from Merck and Fluka and were used
without further purification. Propargylated aldehydes 1a–d and azides 2a–e were pre-
pared according to the reported methods.[19,20] Melting points were obtained on an
Electrothermal 9200 apparatus and were not corrected. Infrared (IR) spectra were
1
recorded on a Fourier transform (FT)–IR 10MB BOMEM spectrometer. H and
13C NMR spectra were recorded on a Bruker DRX-300 Avance spectrometer (300
and 75 MHz, respectively). Mass spectra were determined on a Finnigan-MAT8430
mass spectrometer operating at an ionization potential of 70 eV. Elemental analyses
were performed on an Elementar Analysensysteme GmbH VarioEL, CHNS mode.
General Experimental Procedure for the Synthesis of Title
Compounds 5a–n
A mixture of aromatic propargylated aldehyde 1 (1.0 mmol), azide 2
(1.0 mmol), aniline derivative or ammonium acetate 3 (1.0 mmol), and dimedone 4
(0.28 g, 2.0 mmol) in the presence of Cu(OAc)2 (0.02 g, 10 mol%), sodium ascorbate
(0.04 g, 20% mol), and 1-methylimidazolium triflouroacetate ([Hmim]TFA) (0.02 g,
0.1 mmol) was magnetically stirred in aqueous ethanol [a mixture of H2O=EtOH
(1=1), 5 mL] at 100 ꢀC. After reaction completion (monitored by thin-layer chroma-
tography, TLC, ethyl acetate–n-hexane 1:3), ammonia and water were added and the
mixture was stirred for 30 min. The solid was filtered and washed with hot ethanol to
afford the desired products 5a–n.
Compounds Characterization Data
9-(4-((1-(4-Nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4,6,7-
tetrahydro-3,3,6,6-tetramethyl-10-(3-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-
dione (5a). Light yellow solid, mp 289–291 ꢀC. IR (KBr) (nmax =cmꢁ1): 1650, 1523,
1353, 1224, MS, m=z (%): 688 (Mþ, 7), 568 (25), 393 (58), 366 (100), 273 (100), 129
(61), 83 (44). 1H NMR (300 MHz, DMSO-d6): dH (ppm) 0.73 (6H, s, CH3), 0.87 (6H,
s, CH3), 1.80 (2H, d, J ¼ 16.2 Hz), 2.03 (2H, d, J ¼ 16.2 Hz), 2.21 (4H, m, 2CH2), 5.00
(1H, s, CH), 5.21 (2H, s, CH2), 6.96 (2H, d, HArom, J ¼ 8.1 Hz), 7.28 (2H, d, HArom
,
J ¼ 7.8 Hz), 7.89–8.47 (8H, m, HArom), 9.16 (1H, s, HTriazole). 13C NMR (75 MHz,

3122
M. DABIRI ET AL.
DMSO-d6): dC (ppm) 26.6, 29.6, 32.5, 41.3, 50.0, 61.2, 113.9, 114.5, 121.2, 123.7,
124.8, 126.0, 129.2, 136.0, 137.2, 139.4, 141.2, 147.2, 150.1, 156.6, 195.7. Anal. calcd.
for C38H36N6O7: C, 66.27; H, 5.27; N, 12.20. Found: C, 66.21; H, 5.34; N, 12.27.
9-(4-((3-(4-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4,6,7-
tetrahydro-3,3,6,6-tetramethyl-10-(4-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-
dione (5b). Yellow solid, mp 266–267 ꢀC. IR (KBr) (nmax=cmꢁ1): 1641, 1599, 1528,
1348, 1223. MS, m=z (%): 688 (Mþ, 3), 568 (25), 393 (58), 366 (100), 273 (100), 129
(61), 83 (44). 1H NMR (300 MHz, DMSO-d6): dH (ppm) 0.72 (6H, s, CH3), 0.87 (6H,
s, CH3), 1.77 (2H, m, CH2), 1.98–2.28 (6H, m, 3CH2), 4.99 (1H, s, CH), 5.19 (2H, s,
CH2), 6.93 (2H, t, HArom, J ¼ 8.7 Hz), 7.10 (1H, d, HArom, J ¼ 8.2 Hz), 7.25 (2H, d,
H
Arom, J ¼ 8.1 Hz), 7.74 (2H, d, HArom, J ¼ 9.0 Hz), 8.24 (2H, d, HArom, J ¼ 9.0 Hz),
8.44 (3H, t, HArom, J ¼ 8.1 Hz), 9.14 (1H, s, HTriazole). 13C NMR (75 MHz, DMSO-
d6): dC (ppm) 26.5, 28.2, 29.6, 32.0, 32.6, 50.0, 61.2, 113.0, 113.9, 114.5, 121.2, 125.7,
126.0, 129.1, 133.3, 139.5, 140.2, 144.6, 145.0, 147.2, 149.8, 153.6, 195.6. Anal. calcd.
for C38H36N6O7: C, 66.27; H, 5.27; N, 12.20. Found: C, 66.20; H, 5.32; N, 12.25.
9-(2-((3-(3-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4,6,7-
tetrahydro-3,3,6,6-tetramethyl-10-(3-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-
dione (5c). Orange solid, mp 114–116 ꢀC. IR (KBr) (nmax=cmꢁ1): 1663, 1533, 1356,
1195. MS, m=z (%): 688 (Mþ, 3), 365 (100), 282 (80), 252 (75), 227 (40), 129 (50). 1H
NMR (300 MHz, CDCl3): dH (ppm) 0.83 (6H, s, CH3), 0.98 (6H, s, CH3), 1.80 (2H,
m, CH2), 2.02–2.46 (6H, m, 3CH2), 5.64 (2H, s, CH2), 5.77 (1H, s, CH), 6.83–7.27
(4H, m, HArom), 7.68–7.89 (3H, m, HArom), 8.21–8.69 (4H, m, HArom), 8.69 (1H, s,
H
Arom), 9.32 (1H, s, HTriazole). 13C NMR (75 MHz, CDCl3): dC (ppm) 26.4, 26.8,
29.6, 32.1, 32.6, 50.2, 62.3, 111.9, 115.0, 121.0, 122.7, 124.5, 124.9, 125.7, 127.6,
129.1, 130.7, 131.2, 135.6, 136.0, 138.1, 140.5, 148.6, 148.8, 149.1, 153.9, 196.0,
196.9. Anal. calcd. for C38H36N6O7: C, 66.27; H, 5.27; N, 12.20. Found: C, 66.25;
H, 5.36; N, 12.27.
9-(4-((3-(4-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-10-(4-
chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,
10H)-dione (5d). Light yellow solid, mp 268–270 ꢀC. IR (KBr) (nmax=cmꢁ1): 1639;
1528, 1502, 1365, 1224. MS, m=z (%): 677 (Mþ, 1), 365 (100), 282 (70), 227 (45), 129
(50), 57 (60), 43 (75). 1H NMR (300 MHz, CDCl3): dH (ppm) 0.81 (6H, s, CH3), 0.96
(6H, s, CH3), 1.81 (2H, m, CH2), 2.03–2.63 (6H, m, 3CH2), 5.21 (1H, s, CH), 5.27
(2H, s, CH2), 6.88 (2H, d, HArom, J ¼ 6.3 Hz), 7.20 (2H, d, HArom, J ¼ 7.5 Hz),
7.34 (2H, d, HArom, J ¼ 6.0 Hz), 7.55 (2H, d, HArom, J ¼ 6.0 Hz), 8.00 (2H, d, HArom
,
J ¼ 7.8 Hz), 8.17 (1H, s, HTriazole), 8.42 (d, 2H, HArom, J ¼ 7.5 Hz). 13C NMR
(75 MHz, CDCl3): dC (ppm) 26.8, 29.6, 32.4, 32.5, 41.8, 50.1, 60.1, 113.2, 114.4,
115.4, 120.6, 123.3, 123.7, 125.5, 128.9, 130.5, 132.2, 134.4, 137.7, 137.8, 139.5,
144.9, 148.9, 150.5, 156.5, 196.0. Anal. calcd. for C38H36ClN5O5: C, 67.30; H,
5.35; N, 10.33. Found: C, 67.23; H, 5.42; N, 10.40.
9-(4-((3-(4-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4,6,7-
tetrahydro-3,3,6,6-tetramethyl-10-(3-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-
dione (5e). White solid, mp 240–242 ꢀC. IR (KBr) (nmax=cmꢁ1): 1649, 1534, 1354,
1225. MS, m=z (%): 688 (Mþ, 6), 486 (42), 393 (100), 366 (20), 347 (22), 273 (24),
1
138 (23), 92 (30), 65 (40). H NMR (300 MHz, CDCl3): dH (ppm) 0.72 (6H, s,

TRIAZOLYL METHOXYPHENYL 1,8-DIOXO-DECAHYDROACRIDINES
3123
CH3), 0.87 (6H, s, CH3), 1.76 (2H, d, J ¼ 15.0 Hz, CHAHB), 1.97–2.21 (6H, m,
3CH2), 4.99 (1H, s, CH), 5.20 (2H, s, CH2), 6.96 (2H, d, HArom, J ¼ 8.1 Hz), 7.27
(2H, d, HArom, J ¼ 8.1 Hz), 7.90–8.74 (8H, m, HArom), 9.18 (1H, s, HTriazole). 13C
NMR (75 MHz, CDCl3): dC (ppm) 26.6, 29.6, 31.6, 32.5, 41.3, 50.0, 61.2, 113.9,
114.5, 115.3, 123.6,123.7, 124.8, 129.2, 132.0, 136.0, 137.3, 138.5, 139.4, 139.7,
148.9, 150.1, 156.6, 195.7. Anal. calcd. for C38H36N6O7: C, 66.27; H, 5.27; N,
12.20. Found: C, 66.20; H, 5.34; N, 12.28.
9-(4-((3-(3-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-10-(4-
chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,
10H)-dione (5f). Light cream solid, mp 275–276 ꢀC. IR (KBr) (nmax=cmꢁ1): 1645,
1536, 1363, 1225. MS, m=z (%): 677 (Mþ, 4), 475 (32), 382 (100), 366 (53), 273
1
(50), 64 (25). H NMR (300 MHz, DMSO-d6): dH (ppm) 0.72 (6H, s, CH3), 0.88
(6H, s, CH3), 1.77 (2H, d, J ¼ 17.2 Hz, CHAHB), 1.97–2.22 (6H, m, 3CH2), 4.99
(1H, s, CH), 5.19 (2H, s, CH2), 6.95 (2H, d, HArom, J ¼ 7.8 Hz), 7.24 (2H, d, HArom
J ¼ 7.9 Hz), 7.46 (2H, s, HArom), 7.67 (2H, d, HArom, J ¼ 8.1 Hz), 7.89 (1H, t, HArom
,
,
J ¼ 8.1 Hz), 8.32 (1H, d, HArom, J ¼ 8.1 Hz), 8.41 (d, 1H, HArom, J ¼ 7.8 Hz), 8.73
(1H, s, HArom), 9.17 (1H, s, HTriazole). 13C NMR (75 MHz, DMSO-d6): dC (ppm)
26.6, 29.7, 31.5, 32.4, 39.2, 41.4, 50.0, 61.3, 113.8, 114.5, 115.3, 123.6, 123.7, 126.6,
129.0, 130.5, 132.0, 134.4, 137.6, 137.8, 139.5, 144.9, 148.9, 150.3, 156.5, 195.6. Anal.
calcd. for C38H36ClN5O5: C, 67.30; H, 5.35; N, 10.33. Found: C, 67.20; H, 5.45;
N, 10.44.
9-(2-((3-(4-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4,6,7-
tetrahydro-3,3,6,6-tetramethyl-10-(3-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-
dione (5g). Light cream solid, mp 266–268 ꢀC, IR (KBr) (nmax=cmꢁ1): 1635, 1529,
1357, 1227. MS, m=z (%): 688 (Mþ, 2), 486 (35), 469 (50), 393 (80), 347 (100), 227
1
(30), 64 (28). H NMR (300 MHz, DMSO-d6): dH (ppm) 0.68 (6H, s, CH3), 0.84
(6H, s, CH3), 1.88–2.09 (8H, m, 4CH2), 5.29 (1H, s, CH), 5.42 (2H, s, CH2), 6.87
(1H, s, HArom), 7.09–7.14 (2H, m, HArom), 7.36 (1H, s, HArom), 7.89–8.45 (8H, m,
Arom), 9.22 (1H, s, HTriazole). 13C NMR (75 MHz, DMSO-d6): dC (ppm) 26.3,
H
29.7, 29.9, 32.4, 41.8, 50.1, 61.8, 113.3, 114.5, 121.0, 123.4, 124.7, 126.1, 127.6,
129.2, 131.9, 136.5, 137.6, 140.0, 141.2, 148.5, 149.1, 149.6, 150.4, 156.2, 195.4. Anal.
calcd. for C38H36N6O7: C, 66.27; H, 5.27; N, 12.20. Found: C, 66.16; H, 5.39; N,
12.31.
9-(4-((3-(4-Chlorophenyl)-3H-1,2,3-triazol-4-yl)methoxy)phenyl)-10-(4-
chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,
10H)-dione (5h). Light yellow solid, mp 276–278 ꢀC. IR (KBr) (nmax=cmꢁ1): 1639,
1499, 1366, 1224. MS, m=z (%): 666 (Mþ, 5), 382 (27), 366 (82), 273 (100), 217 (19),
1
164 (45), 111 (20), 83 (18). H NMR (300 MHz, DMSO-d6): dH (ppm) 0.72 (6H, s,
CH3), 0.88 (6H, s, CH3), 1.77 (2H, d, J ¼ 18.0 Hz, CHAHB), 1.97–2.26 (6H, m,
3CH2), 4.99 (1H, s, CH), 5.16 (2H, s, CH2), 6.94 (2H, d, HArom, J ¼ 8.5 Hz), 7.23
(2H, d, HArom, J ¼ 8.3 Hz), 7.46 (2H, s, HArom), 7.67 (4H, d, HArom, J ¼ 8.4 Hz),
7.95 (2H, d, HArom, J ¼ 8.4 Hz), 8.95 (1H, s, HTriazole). 13C NMR (75 MHz,
DMSO-d6): dC (ppm) 26.6, 29.7, 31.5, 32.4, 41.4, 50.0, 61.3, 113.8, 114.5, 122.3,
123.4, 129.0, 130.3, 131.3, 133.5, 134.4, 135.8, 137.8, 139.4, 144.7, 150.3, 156.6,

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M. DABIRI ET AL.
195.5. Anal. calcd. for C38H36Cl2N4O3: C, 68.36; H, 5.44; N, 8.39. Found: C, 68.25;
H, 5.53; N, 8.50.
9-(2-((3-(4-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)-5-nitrophenyl)-
10-(4-chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,
9H,10H)-dione (5i). White solid, mp 272–273 ꢀC. IR (KBr) (nmax=cmꢁ1): 1642,
1518, 1339, 1266, 1225. MS, m=z (%): 722 (Mþ, 4), 520 (29), 503 (50), 382 (83),
1
366 (100), 319 (25), 65 (16). H NMR (300 MHz, CDCl3): dH (ppm) 0.79 (6H, s,
CH3), 0.99 (6H, s, CH3), 1.89–2.28 (8H, m, 4CH2), 5.72 (3H, bs, CH and CH2),
6.95–8.37 (12H, m, HArom), 9.35 (1H, s, HTriazole). 13C NMR (75 MHz, CDCl3): dC
(ppm) 26.0, 26.7, 29.5, 32.5, 41.9, 50.3, 63.2, 111.6, 115.5, 120.3, 122.4,
123.8,124.0, 124.3, 124.8, 125.4, 129.3, 125.9, 137.2, 137.8, 141.4, 141.6, 146.2,
146.9, 150.5, 158.7, 195.9. Anal. calcd. for C38H35ClN6O7: C, 63.11; H, 4.88; N,
11.62. Found: C, 63.00; H, 5.00; N, 11.74.
9-(2-((3-Benzyl-3H-1,2,3-triazol-4-yl)methoxy)-5-bromophenyl)-3,4,6,7-
tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione (5j). Cream
solid, mp 135–138 ꢀC. IR (KBr) (nmax=cmꢁ1): 1638, 1482, 1364, 1223. MS, m=z
(%): 614 (7, Mþ), 442 (16), 426 (18), 359 (10), 272 (56), 183 (16), 144 (80), 115
1
(19), 91 (100), 55 (28). H NMR (300 MHz, CDCl3): dH (ppm) 0.87 (6H, s, CH3),
0.99 (6H, s, CH3), 2.00–2.10 (8H, m, 4CH2), 5.14 (3H, s, CH, CH2), 5.50 (2H, s,
CH2), 6.71–7.49 (9H, m, NH and 8HArom), 7.87 (1H, s, HTriazole). 13C NMR
(75 MHz, CDCl3): dC (ppm) 14.2, 26.9, 29.5, 31.2, 32.4, 40.7, 50.8, 54.2, 60.4, 62.0,
111.7, 113.3, 113.5, 123.6, 128.1, 128.9, 129.3, 129.8, 134.3, 134.8, 136.8, 144.6,
148.9, 155.3, 195.4. Anal. calcd. for C33H35BrN4O3: C, 64.39; H, 5.73; N, 9.10.
Found: C, 64.30; H, 5.82; N, 9.20.
9-(2-((3-(3-Fluorobenzyl)-3H-1,2,3-triazol-4-yl)methoxy)-5-bromophenyl)-
10-(4-chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,
9H,10H)-dione (5k). White solid, mp 238–240 ꢀC. IR (KBr) (nmax=cmꢁ1): 1637,
1483, 1362, 1216. MS, m=z (%): 744 (Mþ, 6), 554 (62), 538 (12), 382 (100), 298
1
(16), 162 (19), 109 (70), 83 (25). H NMR (300 MHz, CDCl3): dH (ppm) 0.79 (6H,
s, CH3), 0.94 (6H, s, CH3), 1.81–2.18 (8H, m, 4CH2), 5.45 (2H, s, CH2), 5.50 (2H,
s, CH2), 5.54 (1H, s, CH), 6.75 (1H, d, HArom, J ¼ 6.6 Hz), 6.96–7.39 (8H, m, HArom),
7.57 (2H, d, HArom, J ¼ 6.6 Hz), 8.21 (1H, s, HTriazole). 13C NMR (75 MHz, CDCl3):
dC (ppm) 26.7, 27.5, 29.5, 32.4, 42.0, 50.2, 53.4, 63.3, 112.9, 114.3, 114.9, 115.3,
123.5, 123.8, 129.9, 130.5, 130.6, 132.7, 135.5, 137.6, 137.8, 149.6, 153.9, 195.5. Anal.
calcd. for C39H37BrClFN4O3: C, 62.95; H, 5.01; N, 7.53. Found: C, 62.81; H, 5.12;
N, 7.60.
9-(2-((3-(4-Nitrophenyl)-3H-1,2,3-triazol-4-yl)methoxy)-5-bromophenyl)-
3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-10-(3-nitrophenyl)acridine-1,8(2H,5H,
9H,10H)-dione (5l). Cream solid, mp 274–275 ꢀC. IR (KBr) (nmax=cmꢁ1): 1644,
1529, 1357, 1227. MS, m=z (%): 766 (Mþ, 3), 427 (63), 393 (100), 377 (66), 347
1
(41), 175 (54), 138 (39), 108 (25), 83 (29), 65 (52). H NMR (300 MHz, DMSO-
d6): dH (ppm) 0.67 (6H, s, CH3), 0.84 (6H, s, CH3), 1.88–2.15 (8H, m, 4CH2), 5.11
(1H, s, CH), 5.43 (2H, s, CH2), 7.18–7.26 (2H, m, HArom), 7.45 (1H, s, HArom),
7.86–7.96 (2H, m, HArom), 8.20 (2H, d, HArom, J ¼ 9 Hz), 8.37–8.47 (4H, m, HArom),
9.17 (1H, s, HTriazole). 13C NMR (75 MHz, DMSO-d6): dC (ppm) 26.2, 29.6, 32.1,

TRIAZOLYL METHOXYPHENYL 1,8-DIOXO-DECAHYDROACRIDINES
3125
32.4, 41.7, 50.0, 61.6, 112.1, 115.3, 121.1, 123.6, 124.7, 125.5, 126.1, 130.0, 131.6,
134.9, 135.9, 140.0, 141.1, 145.2, 147.3, 149.1, 150.9, 155.8, 195.5. Anal. calcd. for
C38H35BrN6O7: C, 59.46; H, 4.60; N, 10.95. Found: C, 59.40; H, 4.67; N, 11.02.
9-(2-((3-(3-Fluorobenzyl)-3H-1,2,3-triazol-4-yl)methoxy)-5-bromophenyl)-
3,4,6,7-tetrahydro-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione (5m).
Orange solid, mp 128–130 ꢀC. IR (KBr) (nmax=cmꢁ1): 1637, 1482, 1365, 1223. MS,
m=z (%): 632 (Mþ, 3), 481 (26), 272 (63), 215 (20), 162 (30), 109 (100), 83 (54), 43
(32). 1H NMR (300 MHz, CDCl3): dH (ppm) 0.86 (6H, s, CH3), 0.99 (6H, s,
CH3), 2.09–2.46 (8H, m, 4CH2), 4.59 (1H, s, CH), 5.21 (2H, s, CH2), 5.51 (2H, s,
CH2), 6.57–7.42 (8H, m, NH and 7HArom), 8.07 (1H, s, HTriazole). 13C NMR
(75 MHz, CDCl3): dC (ppm) 26.6, 26.9, 29.4, 29.7, 30.6, 32.4, 40.5, 50.9, 53.5, 62.5,
113.3, 113.6, 114.1, 114.9, 115.3, 115.6, 115.9, 123.8, 129.8, 130.7, 130.8, 133.9,
137.2, 137.5, 150.1, 155.1, 161.3, 164.5, 195.9. Anal. calcd. for C33H34BrFN4O3: C,
62.56; H, 5.41; N, 8.84. Found: C, 62.45; H, 5.52; N, 8.97.
9-(2-((3-(3-Fluorobenzyl)-3H-1,2,3-triazol-4-yl)methoxy)-5-bromophenyl)-
3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-10-(3-nitrophenyl)acridine-1,8(2H,5H,
9H,10H)-dione (5n). Light yellow solid, mp 258–259 ꢀC. IR (KBr) (nmax=cmꢁ1):
1637, 1483, 1362, 1216. MS, m=z (%): 739 (Mþ, 3), 427 (75), 393 (100), 377 (60),
1
108 (25), 83 (30). H NMR (300 MHz, CDCl3): dH (ppm) 0.78 (6H, s, CH3), 0.93
(6H, s, CH3), 1.76–2.18 (8H, m, 4CH2), 5.42 (1H, s, CH), 5.50 (2H, s, CH2),
6.76–8.19 (11H, m, HArom), 8.43 (1H, s, HTriazole). 13C NMR (75 MHz, CDCl3): dC
(ppm) 26.7, 28.2, 29.5, 42.2, 50.0, 53.5, 63.0, 113.0, 114.2, 114.9, 115.2, 115.4,
115.7, 123.6, 124.5, 124.8, 130.0, 130.6, 130.7, 131.3, 133.2, 135.9, 137.0, 140.4,
148.9, 154.2, 195.6. Anal. calcd. for C38H35BrFN5O5: C, 61.63; H, 4.76; N, 9.46.
Found: C, 61.56; H, 4.84; N, 9.55.
4-((1-(4-Nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde (6).
Orange solid, mp 182–183 ꢀC. IR (KBr) (vmax, cmꢁ1): 3078, 2747, 1691, 1593,
1
1516, 1247. MS, m=z (%): 324 (Mþ, 20), 267 (50), 175 (63), 129 (100), 76 (60). H
NMR (300 MHz, DMSO-d6): dH (ppm) 5.37 (2H, s, CH2), 7.23–8.39 (8H, m, HArom),
9.16 (1H, s, HArom), 9.85 (1H, s, CHO). 13C NMR (75 MHz, DMSO-d6): dC (ppm)
61.7, 115.6, 121.1, 123.9, 125.9, 130.4, 132.2, 141.1, 144.3, 147.2, 163.2, 191.7. Anal.
calcd. for C16H12N4O4: C, 59.26; H, 3.73; N, 17.28. Found: C, 59.13; H, 3.85;
N, 17.41.
ACKNOWLEDGMENTS
We gratefully acknowledge financial support from the Research Council of
Shahid Beheshti University and the Catalyst Center of Excellence (CCE).
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