TiO2 nanoparticles as an efficient catalyst for the one-pot preparation of Tetrahydrobenzo[c]acridines in aqueous media

Article abstract of DOI:10.5560/ZNB.2013-2323

A series of tetrahydrobenzo[c]acridinone derivatives have been prepared by a one-pot fourcomponent reaction of 1-naphthol, aromatic aldehydes, dimedone, and ammonium acetate in aqueous media using a catalytic amount of titanium dioxide nanoparticles (TiO₂ NPs). The advantages of this novel protocol include the excellent yields, operational simplicity, short reaction time, easy work-up, reusability of the catalyst and an environmentally friendly procedure.

Full text of DOI:10.5560/ZNB.2013-2323

TiO2 Nanoparticles as an Efficient Catalyst for the One-pot Preparation
of Tetrahydrobenzo[c]acridines in Aqueous Media
Shahrzad Abdolmohammadi, Mahdieh Mohammadnejad and Faezeh Shafaei
Department of Chemistry, Faculty of Science, East Tehran Branch, Islamic Azad University,
P. O. Box 33955-163, Tehran, I. R. Iran
Reprint requests to Prof. Dr. Shahrzad Abdolmohammadi. Tel: +98-21-3359 4950.
Fax: +98-21-3359 4332. E-mail: abdolmohamadi sh@yahoo.com and s.abdolmohamadi@iauet.ac.ir
Z. Naturforsch. 2013, 68b, 362 – 366 / DOI: 10.5560/ZNB.2013-2323
Received December 7, 2012; in revised form January 25, 2013
A series of tetrahydrobenzo[c]acridinone derivatives have been prepared by a one-pot four-
component reaction of 1-naphthol, aromatic aldehydes, dimedone, and ammonium acetate in aqueous
media using a catalytic amount of titanium dioxide nanoparticles (TiO2 NPs). The advantages of this
novel protocol include the excellent yields, operational simplicity, short reaction time, easy work-up,
reusability of the catalyst and an environmentally friendly procedure.
Key words: Aqueous Media, Domino Knoevenagel-Michael Condensation,
Tetrahydrobenzo[c]acridinones, TiO2 Nanoparticles
Introduction
prominent members of this group have been used as
chemotherapeutic agents against cancer cells [28]. In
The utility of heterogeneous catalysts in synthetic the field of antitumor DNA-binding agents, this class
chemistry has been increasingly recognized in the last of acridine derivatives play an important role regard-
few years [1 – 6]. It was shown that one of the effi- ing both the number of active compounds and their
cient synthetic methods is to perform reactions on the DNA binding affinity [29]. Although several meth-
surface of metal oxides such as SiO2, Al2O3, ZnO, ods have been reported previously [30 – 37] there is
etc. [7 – 15]. The most preferred solids would be those always a need for efficient methods for the synthe-
which are easy to handle, inexpensive, non-toxic and sis of these biologically important compounds. In
easily removed during work-up. TiO2 nanoparticles the present study, we designed a new simple one-
(TiO2 NPs) as an inexpensive, non-toxic, moisture- pot four-component reaction of 1-naphthol (1), aro-
stable, reusable, commercially available colorless pow- matic aldehydes 2, dimedone (3), and ammonium ac-
der has been of great interest to many scientists in etate (4) to afford 7-aryl-10,10-dimethyl-7,10,11,12-
recent years. Several applications of these nanoparti- tetrahydrobenzo[c]acridin-8(9H)-ones 5, which is cat-
cles as effective catalysts in green synthetic organic alyzed by 10 mol-% of commercially available TiO2
chemistry have been already highlighted in the liter- NPs with an average particle size of 15 nm, in aqueous
ature [16 – 23]. It has been our interest to elaborate media at 80 ◦C (Scheme 1).
another significant catalytic activity of TiO2 NPs for
the synthesis of tetrahydrobenzo[c]acridinone deriva-
tives 5a–h by a one-pot four-component reaction of
Results and Discussion
1-naphthol, aromatic aldehydes, dimedone, and ammo-
nium acetate in aqueous media.
As a starting point of this investigation, we chose the
It is well known that the acridine core structure is reaction of 1-naphthol (1), 3-nitrobenzaldehyde (2h),
an important heterocyclic framework that can be found dimedone (3), and ammonium acetate (4), as a model
in numerous biologically active compounds, which to explore the appropriate conditions (Scheme 2).
are widely used as antibacterial, antifungal [24], anti- A summary of the optimization experiments is shown
malarial [25], and anticancer [26, 27] agents. The most in Table 1.
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S. Abdolmohammadi et al. · One-pot Preparation of Tetrahydrobenzo[c]acridines in Aqueous Media
363
Table 1. The synthesis of acridin-8(9H)-one 5h from 1-
naphthol (1), 3-nitrobenzaldehyde (2h), dimedone (3), and
ammonium acetate (4) under different conditions.
O
OH
Ar
O
Ar
H
TiO2 NPs (10 mol-%)
H2O, 80 °C
CH3
CH3
Entry Catalyst (mol-%)
Solvent Temp.
(◦C)
Time
(h)
Yield
(%)a
1
O
2
N
H
+
1
2
3
4
5
6
7
8
9
no catalyst
H2O
H2O
H2O
H2O
H2O
H2O
neat
neat
80
80
80
80
60
90
90
80
80
80
10
2
2
2
6
4
8
2
4
5
48
53
98
96
59
97
trace
71
86
76
5
CH3
CH3
TiO2 NPs (5%)
TiO2 NPs (10%)
TiO2 NPs (20%)
TiO2 NPs (10%)
TiO2 NPs (10%)
no catalyst
TiO2 NPs (10%)
TiO2 NPs (10%)
TiO2 NPs (10%)
NH4OAc
O
4
3
Scheme 1.
NO2
O
NO2
CH3CN
CH2Cl2
10
OH
a
CHO
Isolated yield.
TiO2 NPs (10 mol-%)
H2O, 80 °C
CH3
CH3
1
2h
N
H
+
O
Table 2. Synthesis of acridin-8(9H)-ones 5a–h catalyzed by
TiO2 NPs.
5h
CH3
CH3
NH4OAc
O
Product
Ar
Time (h) M. p. (◦C) Yield (%)a
3
4
5a
5b
5c
5d
5e
5f
4-BrC6H4
2-ClC6H4
4-ClC6H4
2,4-Cl2C6H3
3,4-Cl2C6H3
4-HOC6H4
4-CH3OC6H4
3-NO2C6H4
2
3
2.5
3
2.5
2
2.5
2
277 – 278
275 – 277
263 – 265
279 – 280
285 – 287
315 – 317
259 – 260
268 – 270
98
97
98
95
96
97
95
98
Scheme 2.
The results have shown that the use of just 10 mol-
% of TiO2 NPs is sufficient to push the reaction for-
ward (Table 1, entries 1 – 4). To evaluate the optimum 5h
5g
reaction temperature, the reaction was examined at dif-
ferent temperatures. The optimal reaction temperature
was found to be 80 ◦C (Table 1, entries 3 and 5 – 6).
a
Yields refer to those of pure isolated products.
In the absence of any solvent and catalyst the reac- ate 7 to produce the Michael adduct 8. Intramolecular
tion proceeded poorly (Table 1, entry 7). When the cyclization of 8 gives product 5, after dehydration.
same reaction was carried out in various solvents such
To check the recyclability the catalyst (TiO2 NPs)
as CH3CN, CH2Cl2, H2O and also under solvent-free was centrifuged from the reaction mixture after adding
conditions, it was revealed that the reaction performed DMF, and dried in vacuo. It could then be reused for
in aqueous media gave the best results (Table 1, entries further catalytic reactions. In each cycle > 81% of the
3 and 8 – 10).
catalyst was easily recovered. As shown in Table 3, the
To explore the scope of this novel efficient method, yields of the model reaction after the second and third
a reaction of 1-naphthol, dimedone and ammonium ac- uses of the catalyst were almost the same without loss
etate with various substituted aryl aldehydes was eval- of catalytic activity.
uated (Table 2).
According to both Lewis acid and Lewis base char- Conclusion
acter of metal oxides [38], a suggested mechanism for
the formation of tetrahydrobenzo[c]acridinone deriva-
In conclusion, an efficient green method for
tives 5 is shown in Scheme 3. It is reasonable to as- the preparation of 7-aryl-10,10-dimethyl-7,10,11,12-
sume that TiO2 NPs are coordinated to the oxygen tetrahydrobenzo[c]acridin-8(9H)-one derivatives by
atom of the aromatic aldehyde 2 activating it for nu- a domino Knoevenagel-Michael condensation of 1-
cleophilic attack [39]. Knoevenagel condensation be- naphthol, aromatic aldehydes, dimedone, and ammo-
tween 2 and enamine 6, previously formed from the nium acetate, catalyzed by TiO2 NPs in aqueous me-
reaction of dimedone (3) and ammonium acetate (4), dia, was achieved. This novel method has the advan-
generates alkene 7. 1-Naphthol (1) adds to intermedi- tages of high yields, mild reaction conditions, short re-
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S. Abdolmohammadi et al. · One-pot Preparation of Tetrahydrobenzo[c]acridines in Aqueous Media
O
O
NH4OAc
4
(4, 1 mmol), and commercially available TiO2 NPs (Sigma-
Aldrich) with an average diameter of 15 nm (7.9 mg, 10 mol-
O
+
Ar
H
%) was stirred at 80 ◦C in water (10 mL). After completion
of the reaction (TLC), the reaction mixture was filtered. The
solid mass was eluted with DMF (5 mL), and the mixture was
centrifuged at 2000 – 3000 rpm for 5 min to remove the nano
TiO2 catalyst. The organic solution was then poured into cold
water (15 mL), filtered and washed with aqueous ethanol to
afford the pure products 5 in high yields.
O
H2N
3
6
2
TiO2 NPs
O
O
OH
H
TiO2 NPs
NH
H
+
H
O
Ar
O
Ar
NH2
7-(4-Bromophenyl)-10,10-dimethyl-
Ti
O
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5a)
1
7
Colorless powder; yield 0.424 g (98%); m. p.
277 – 278 ◦C (lit.: 278 – 280 ◦C [37]). – IR (KBr): ν = 3291,
2941, 1682, 1576, 1522 cm−1. – 1H NMR: δ = 0.98 (s, 3 H,
CH3), 1.06 (s, 3 H, CH3), 2.05 (d, 1 H, J = 16.0 Hz, H-11),
2.25 (d, 1 H, J = 16.0 Hz, H-11), 2.66 (d, 1 H, J = 16.2 Hz,
H-9), 2.72 (d, 1 H, J = 16.2 Hz, H-9), 5.21 (s, 1 H, CH), 7.17
(d, 2 H, J = 8.0 Hz, HAr), 7.25 (d, 1 H, J = 8.0, Hz HAr),
7.37 (d, 2 H, J = 8.2 Hz, HAr), 7.39 (d, 1 H, J = 8.0 Hz,
HAr), 7.49 (m, 3 H, HAr), 7.83 (d, 1 H, J = 8.2, Hz HAr),
8.47 (d, 1 H, J = 8.4 Hz, HAr), 9.30 (s, 1 H, NH) ppm. –
Anal. for C25H22BrNO (432.36): calcd. C 69.45, H 5.13, N
3.24; found C 69.51, H 5.21, N 3.19%.
TiO2 NPs
O
O
H O,
TiO2 NPs
2
Ar
Ar
NH
NH
O
H
OTi
O
8
5
Scheme 3.
Table 3. Reuse of TiO2 NPs for the synthesis of 5h.
7-(2-Chlorophenyl)-10,10-dimethyl-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5b)
Recycles
Yield (%)a
Recovery of catalyst (%)
1
2
3
98
93
91
90
85
81
Colorless powder; yield 0.376 g (97%); m. p.
275 – 277 ◦C (lit.: 275 – 278 ◦C [37]). – IR (KBr): ν = 3311,
2945, 2854, 1667, 1579, 1515 cm−1. – 1H NMR: δ = 1.04
(s, 3 H, CH3), 1.10 (s, 3 H, CH3), 2.02 (d, 1 H, J = 16.2 Hz,
H-11), 2.24 (d, 1 H, J = 16.2 Hz, H-11), 2.69 (d, 1 H,
J = 16.4 Hz ,H-9), 2.77 (d, 1 H, J = 16.4 Hz, H-9), 5.74 (s, 1
H, CH), 7.27 (m, 8 H, HAr), 7.80 (d, 1 H, J = 7.8 Hz, HAr),
8.47 (d, 1 H, J = 8.2 Hz, HAr), 9.26 (s, 1 H, NH) ppm. –
Anal. for C25H22ClNO (387.91): calcd. C 77.41, H 5.72, N,
3.61; found C 77.36, H 5.78, N 3.49%.
a
Isolated yield.
action time, easy work-up, recyclability of the catalyst,
and an environmentally friendly procedure.
Experimental Section
Materials and methods
All of the chemical materials used in this work were pur-
chased from Merck and Sigma-Aldrich and used without fur-
ther purification. Melting points were determined on an Elec-
trothermal 9100 apparatus and are uncorrected. IR spectra
were obtained on an ABB FT-IR (FTLA 2000) spectrom-
eter. 1H NMR spectra were recorded on a Bruker DRX-
500 AVANCE instrument at 500 MHz, using TMS as inter-
nal standard and [D6]DMSO as solvent. Elemental analyses
were carried out using a Heraeus CHN rapid analyzer.
7-(4-Chlorophenyl)-10,10-dimethyl-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5c)
Colorless powder; yield 0.38 g (98%); m. p. 263 – 265 ◦C
(lit.: 265 – 266 ◦C [37]). – IR (KBr): ν = 3303, 2966, 1672,
1589, 1516 cm−1. – 1H NMR: δ = 0.98 (s, 3 H, CH3), 1.08
(s, 3 H, CH3), 2.05 (d, 1 H, J = 16.1 Hz, H-11), 2.25 (d, 1
H, J = 16.1 Hz, H-11), 2.66 (d, 1 H, J = 16.6 Hz, H-9), 2.73
(d, 1 H, J = 16.6 Hz, H-9), 5.23 (s, 1 H, CH), 7.23 (m, 5 H,
HAr), 7.49 (m, 2 H, HAr), 7.59 (m, 1 H, HAr), 7.83 (d, 1 H,
J = 8.4 Hz, HAr), 8.47 (d, 1 H, J = 8.4 Hz, HAr), 9.31 (s, 1 H,
General procedure for the preparation of compounds 5a–h
A mixture of 1-naphthol (1, 1 mmol), an aromatic alde- NH) ppm. – Anal. for C25H22ClNO (387.91): calcd. C 77.41,
hyde 2 (1 mmol), dimedone (3, 1 mmol), ammonium acetate H 5.72, N 3.61; found C 77.38, H 5.64, N 3.52%.
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7-(2,4-Dichlorophenyl)-10,10-dimethyl-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5d)
3H, HAr), 7.81 (d, 1H, HAr, J = 7.4 Hz), 8.44 (1H, d, HAr
,
J = 8.2 Hz), 9.08 (s, 1H, OH), 9.20 (s, 1H, NH) ppm. –
Anal. for C25H23NO2 (469.46): calcd. C 81.27, H 6.28, N
3.79; found C 81.35, H 6.21, N 3.63%.
Colorless powder; yield 0.401 g (95%); m. p.
279 – 280 ◦C (lit.: 280 – 282 ◦C [37]).
– IR (KBr):
ν = 3313, 2952, 1682, 1589, 1517 cm−1. – 1H NMR:
δ = 1.02 (s, 3H, CH3), 1.10 (s, 3H, CH3), 2.02 (d, 1H, H-11,
J = 16.1 Hz), 2.24 (d, 1H, H-11, J = 16.1 Hz), 2.63 (d, 1H,
H-9, J = 16.4 Hz), 2.73 (d, 1H, H-9, J = 16.4 Hz), 5.71 (s,
1H, CH), 7.20 (d, 1H, HAr, J = 8.4 Hz), 7.26 (m, 2H, HAr),
7.45 (d, 1H, HAr, J = 8.2 Hz), 7.55 (m, 3H, HAr), 7.81 (d,
1H, HAr, J = 7.4 Hz), 8.47 (d, 1H, HAr, J = 7.4 Hz), 9.30 (s,
1H, NH) ppm. – Anal. for C25H21Cl2NO (422.35): calcd. C
71.10, H 5.01, N 3.32; found C 71.03, H 4.94, N 3.24%.
10,10-Dimethyl-7-(4-methoxyphenyl)-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5g)
Colorless powder; yield 0.364 g (95%); m. p.
259 – 260 ◦C (lit.: 257 – 258 ◦C [37]). – IR (KBr): ν = 3290,
2961, 2915, 1661, 1598, 1514 cm−1. – 1H NMR: δ = 1.00
(s, 3 H, CH3), 1.08 (s, 3 H, CH3), 2.04 (d, 1 H, J = 16.1 Hz,
H-11), 2.24 (d, 1 H, J = 16.1 Hz, H-11), 2.65 (d, 1 H,
J = 16.4 Hz, H-9), 2.73 (d, 1 H, J = 16.4 Hz, H-9), 5.14
(s, 1 H, CH), 6.73 (d, 2 H, J = 8.2 Hz, HAr), 6.99 (d, 2 H,
J = 8.2 Hz, HAr), 7.25 (d, 1 H, J = 8.2 Hz, HAr), 7.47 (m,
3 H, HAr), 7.81 (d, 1 H, J = 8.0 Hz, HAr), 8.45 (1 H, d,
J = 8.2 Hz, HAr), 9.23 (s, 1 H, OH), 9.20 (s, 1 H, NH). ppm.
– Anal. for C26H25NO2 (383.49): calcd. C 81.43, H 6.57, N
3.65; found C 81.39, H 6.51, N 3.61%.
7-(3,4-Dichlorophenyl)-10,10-dimethyl-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5e)
Colorless powder; yield 0.405 g (96%); m. p.
285 – 287 ◦C (lit.: 284 – 286 ◦C [37]). – IR (KBr): ν = 3319,
2952, 1684, 1583, 1520 cm−1. – 1H NMR: δ = 1.00 (s, 3 H,
CH3), 1.09 (s, 3 H, CH3), 2.07 (d, 1 H, J = 16.2, Hz H-11),
2.26 (d, 1 H, J = 16.2 Hz, H-11), 2.67 (d, 1 H, J = 17.2 Hz,
H-9), 2.76 (d, 1 H, J = 17.2 Hz, H-9), 5.28 (s, 1 H, CH), 7.17
(dd, 1 H, J = 8.4, 2.0 Hz, HAr), 7.30 (d, 1 H, J = 8.2 Hz,
HAr), 7.48 (m, 5 H, HAr), 7.84 (d, 1 H, J = 8.1 Hz, HAr),
8.48 (d, 1 H, J = 8.6 Hz, HAr), 9.34 (s, 1 H, NH) ppm. –
Anal. for C25H21Cl2NO (422.35): calcd. C 71.10, H 5.01, N
3.32; found C 71.19, H 5.08, N 3.28%.
10,10-Dimethyl-7-(3-nitrophenyl)-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5h)
Colorless powder; yield 0.39 g (98%); m. p. 268 – 270 ◦C
(lit.: 267 – 269 ◦C [37]). – IR (KBr): ν = 3288, 2935, 2854,
1666, 1573, 1529, 1516 cm−1. – 1H NMR: δ = 0.99 (s, 3 H,
CH3), 1.11 (s, 3 H, CH3), 2.06 (d, 1 H, J = 16.2 Hz, H-11),
2.58 (d, 1 H, J = 16.2 Hz, H-11), 2.70 (d, 1 H, J = 16.4 Hz,
H-9), 2.75 (d, 1 H, J = 16.4 Hz, H-9), 5.43 (s, 1 H, CH), 7.33
(d, 1 H, J = 8.4 Hz, HAr), 7.52 (m, 3 H, HAr), 7.61 (m, 1 H,
HAr), 7.72 (d, 1 H, J = 7.8 Hz, HAr), 7.84 (d, 1 H, J = 7.8 Hz,
HAr), 8.00 (m, 2 H, HAr), 8. 48 (d, 1 H, J = 8.6 Hz, HAr), 9.42
(s, 1 H, NH) ppm. – Anal. for C25H22N2O3 (398.46): calcd.
C 75.36, H 5.57, N 7.03; found C 75.44, H 5.51, N 7.10%.
7-(4-Hydroxyphenyl)-10,10-dimethyl-
7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one (5f)
Colorless powder; yield 0.455 g (97%); m. p.
315 – 317 ◦C (lit.: 312 – 315 ◦C [37]). – IR (KBr): ν = 3293,
2968, 2910, 1668, 1574, 1521 cm−1. – 1H NMR: δ = 1.00
(s, 3H, CH3), 1.08 (s, 3H, CH3), 2.04 (d, 1H, H-11,
J = 16.0 Hz), 2.23 (d, 1H, H-11, J = 16.0 Hz), 2.64 (d, 1H,
H-9, J = 16.4 Hz), 2.72 (d, 1H, H-9, J = 16.4 Hz), 5.08
(s, 1H, CH), 6.55 (d, 2H, HAr, J = 8.2 Hz), 6.99 (d, 2H,
Acknowledgement
S. A. would like to thank the East Tehran Branch, Islamic
HAr, J = 8.2 Hz), 7.24 (d, 1H, HAr, J = 8.4 Hz), 7.48 (m, Azad University for financial support.
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