Microwave-assisted multicomponent reactions: Rapid and regioselective formation of new extended angular fused aza-heterocycles

Article abstract of DOI:10.2174/138620712800194459

A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzo[h]naphtho[2,3-a]acridine-15,16(5H,14H)-diones has been established. The reaction can be conducted by using readily available and inexpensive substra

Full text of DOI:10.2174/138620712800194459

400
Combinatorial Chemistry & High Throughput Screening, 2012, 15, 400-410
Microwave-Assisted Multicomponent Reactions: Rapid and Regioselective
Formation of New Extended Angular Fused Aza-Heterocycles
Shu-Liang Wang, Ge Zhang, Ding Jie, Bo Jiang*, Xing-Han Wang and Shu-Jiang Tu*
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional
Materials, Xuzhou Normal University, Xuzhou 221116, P.R. China
Abstract: A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized
benzo[h]naphtho[2,3-a]acridine-15,16(5H,14H)-diones has been established. The reaction can be conducted by using
readily available and inexpensive substrates under microwave irradiation. The procedures are facile, avoiding time-
consuming and costly syntheses, tedious work-up and purifications of precursors as well as protection/deprotection of
functional groups. This method is much more efficient due to short reaction times and easy work up. The resulting
naphthoacridines have been readily converted into benzoquinoxaline-fused benzoquinoline analogues by treating with
benzene-1,2-diamine under microwave irradiation. The structural assignment has been ambiguously confirmed by X-ray
analysis. A new mechanism has been proposed for this new multicomponent domino process.
Ar
O
O
O
Ar
N
O
HOAc
MW
+
OH
O
NH2
8 -12 min
(74 - 88%, 31 examples)
H2N
H2N
N
Ar
N
N
DMF, MW
16 - 20 min
(79 - 91%, 19 examples)
Keywords: Benzoquinoxaline-fused benzoquinolines, microwave-assisted synthesis, multicomponent reaction,
naphthoacridines, regioselectivity.
INTRODUCTION
energy and long lifetime, which have been tested and applied
as an efficient photocatalyst in modeling the photosynthetic
reactions [2]. Furthermore, the linear fuzed acridones, i.e. the
oxidized derivatives of acridines, are well-known organic
pigments and have been extensively studied for their self-
assembling [3] photoconductive, doping dye emitter [4] and
fluorescent [5] properties in numerous devices stemmed
from materials chemistry.
The charge-transport materials can be used in organic
electronic devices such as organic light-emitting diodes
(OLED), lasers, photovoltaic cells, photodetectors, active
and passive electronic devices, and memories [1]. The
extended angular fused aza-heterocycles (V-type fused aza-
heterocycles) exhibit important photophysics properties,
which are widely applied in the charge-transport materials
due to their strong skeleton rigidity and large ꢀ-conjugation
systems. With large ꢀ-conjugation systems, benzacridine
derivatives, especially benzophenazine-fused benzacridine,
possess interesting photophysical properties such as the
presence of intramolecular electron-transfer state of a high
Dihydroacridines with an 1,4-DHPs parent nucleus are
well known as therapeutic agents [6]. Due to their interesting
biological activities such as antimalarial and antitumor, they
have immense utility in pharmaceutical industry [7].
Therefore, this class of compounds has been the focus of
much recent research [8], and has led to intensive interest in
the synthesis of several drugs based on them [9]. However,
their derivatives having further extended conjugated systems
such as the benzophenazine-fused benzacridine derivatives
have been seldom reported so far. Therefore, a simple,
efficient and direct synthetic route for this important class of
heterocycles is strongly desired.
*Address correspondence to these authors at the School of Chemistry and
Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic
Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou
221116, P.R. China; Tel: 0086-516-83500065; Fax: 0086-516-83500065;
E-mails: jiangchem@xznu.edu.cn; laotu@xznu.edu.cn, laotu2001@263.net
1875-5402/12 $58.00+.00
© 2012 Bentham Science Publishers

Microwave-Assisted Multicomponent Reactions
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5 401
Ar
O
O
O
Ar
N
O
HOAc
MW
+
OH
O
NH2
8 -12 min
(74 - 87%, 25 examples)
H2N
H2N
N
Ar
N
N
DMF, MW
16 - 20 min
(81 - 90%, 14 examples)
Scheme 1. The domino synthesis of benzophenazine-fused benzacridines.
In the past several years, our group has developed
various multicomponent domino reactions that can provide
easy access to functionalized multiple heterocycles [10-12].
Among these reactions is a four-component domino process
for concise synthesis of multi-functionalized quinazoline
derivatives [10a]. Furthermore, we have also found that when
aliphatic aldehydes were employed to replace their aromatic
counterparts, the reaction proceeded along another pathway
leading to the formation of multi-functionalized
tricyclo[6.2.2.01,6]dodecanes [10b].
to 4. If the product 5 with para-diketone unit was provided,
the reaction between product 5 and benzene-1,2-diamine did
not further take place. On the contrary, the product 4 with
ortho-dicarbonyl groups if provided can react with benzene-
1,2-diamine to generate fused aza-heterocycles with big ꢀ-
conjugate system. Based on the above analyse, we employed
4-chlorobenzaldehyde 1a to react with 2-hydroxy-1,4-
naphthoquinone 2 and naphthalen-2-amine 3a in HOAc
under microwave heating. After filtration, a red solid was
obtained in 70% chemical yield. When the synthsized red
solid was subjected with benzene-1,2-diamine, the yellow
precipitates were observed. All of the analytical data showed
that a benzene-1,2-diamine unit was introduced in the final
product, and a novel heptacyclic benzophenazine fused
benzoquinoline 7a was produced in high yield (Scheme 1).
This product has been fully characterized by 1H NMR,
HRMS and IR spectral analysis. Furthermore, the structure
of 7g has been unambiguously determined by X-ray
structural analysis as shown in Fig. (1). Thus, instead of
compound 5, the structure of red solid described above was
dibenzo[a,h]acridine-12,13(7H,14H)-dione 4 established on
this experimental results. This surprising result is of value to
us not only because we are interested in the design of the
new regioseclective domino reaction but also because we
were unable to find examples of other methods allowing for
such convenient synthesis in related literature.
During our continuous efforts on searching for useful
multicomponent domino reactions [10-12], we now report a
new regioselective multicomponent domino annulation
which provides an easy access to benzo[h]naphtho[2,3-
a]acridines and their derivatives. This reaction was achieved
by reacting aldehydes, aromatic amines and 2-hydroxy-1,4-
naphthoquinone under microwave irradiation (MW) in the
absence of strong acids or metal catalysts/promoters
(Scheme 1). The resulting benzo[h]naphtho[2,3-a]acridines
has been reacted with benzene-1,2-diamine to give
polycyclic heteroaromatics, benzophenazine-fused benzacri-
dine. To the best of our knowledge, an efficient domino
approach to extended angular fused aza-heterocycle, such as
heptacyclic, cctocyclic or nonacyclic-fused benzo[h]naphtho
[2,3-a]acridines, has not been well documented. In this
paper, we would like to report the new reaction for their
syntheses by controlling reaction substrates and sequence.
Next, we choose the most appropriate solvent for the
reaction of 4-chlorobenzaldehyde 1a with 2-hydroxy-1,4-
naphthoquinone
2
and naphthalen-2-amine 3a. This
RESULTS AND DISCUSSION
heterocyclization reaction was examined at 100oC using
water, EtOH, glycol, N,N-dimethylformamide (DMF) and
acetic acid (AcOH) (Table 1) as the solvent. As shown in
Table 1, the use of acetic acid at 120oC allowed the direct
conversion of 2-hydroxy-1,4-naphthoquinone 2 into the
corresponding dibenzo[a,h]acridine-12,13(7H,14H)-dione 4a
in a yield of 83% under microwave irradiation condition
It has been reported that when a mixture of aldehyde, 2-
hydroxy-1,4-naphthoquinone and naphthalen-2-amine was
stirred in [bmim]BF4 at room temperature, a cycloadduct
dibenzo[a,i]acridine-1,6-diones 5 were produced in high
yields [13]. After analyzing reaction mechanism, we
reasoned that this reaction may have two different routes to
the final products 4 or 5: route i to the prodcut 5, and route ii

402 Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5
Wang et al.
O
O
Ar
N
H
5
route i
O
Ar
O
O
O
O
Ar
O
3a
O
Ar
H2N
+
ii
O
O
OH
i
NH2
2
1
A
B
route ii
NH2
O
Ar
N
Ar
N
6a
NH2
O
N
N
H
7
4
Scheme 2. Synthesis of products 4 or 5.
Table 1. Conditions Optimization for the Synthesis of 4a
(Table 1, entry 5). Other polar solvents, such as ethanol,
ethylene glycol, N,N-dimethylformamide, and water,
resulted in moderate to poor to modest yields of 40%-65%
(Table 1, entries 1-4). The reaction proceeded rapidly to
completion within a few minutes at 120oC. Increasing
reaction temperature to 140oC did not improve chemical
yields.
Entry
Solvent
T/oC
Time (min)
Yield/%a
1
2
3
4
Water
EtOH
Glycol
DMF
120
120
120
120
120
8
8
8
8
8
40
60
56
65
83
5
AcOH
aIsolated yield.
Encouraged by the above interesting results, we utilized
various aromatic aldehydes with different substituents under
the same reaction conditions. The results are shown in Table
2. From these results, we could see that all of the reactions
proceeded smoothly to afford the corresponding
dibenzo[a,h]acridine-12,13(7H,14H)-dione 4 in good yields
(75-83%). Aromatic aldehydes carrying either electron-
donating or electron-withdrawing substituents showed
similar reactivity and reacted efficiently to yield the desired
product. Moreover, heterocyclic aldehydes such as
thiophene-2-carbaldehyde (Table 2, entry 14) also displayed
a high reactivity under this standard condition. Bedsides
naphthalen-2-amine (3a) substrate, anthracen-2-amine (3b)
was also proven to be suitable for the reaction with 2-
hydroxy-1,4-naphthoquinone (2) and sixteen arylaldehydes
bearing electron-withdrawing or electron-donating groups to
give the corresponding benzo[h]naphtho[2,3-a]acridine-
Fig. (1). ORTEP drawing of 7g.

Microwave-Assisted Multicomponent Reactions
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5 403
Table 2. The Three-Component Synthesis of Products 4a-4y
Table 3. The Synthesis of Products 7
Entry 4a
Ar =
3
Time b
Yield c
Entry
Product
Diamine
4
Time/Min
Yield/%b
1
2
4a 4-Chlorophenyl (1a)
4b 2-Chlorophenyl(1b)
4c 2,4-Dichlorophenyl(1c)
4d 4-Fluorophenyl(1d)
4e 4-Bromophenyl(1e)
4f 4-Nitrophenyl(1f)
3a
3a
3a
3a
3a
3a
3a
3a
3a
3a
3a
3a
8
8
83
82
77
83
82
80
82
79
81
81
75
79
81
76
85
78
83
87
80
81
82
75
79
74
78
1
2
7a
7b
7c
7d
7e
7f
6a
6a
6a
6a
6a
6a
6a
6a
6a
6a
6a
6a
6b
6b
4a
4b
4h
4i
20
18
18
16
20
20
20
20
18
16
18
20
20
20
90
89
81
82
89
82
89
86
87
83
82
88
84
81
3
7
3
4
8
4
5
7
5
4j
6
10
8
6
4k
4l
7
4g Phenyl(1g)
7
7g
7h
7i
8
4h 4-Tolyl(1h)
8
8
4m
4q
4r
4p
4w
4r
4x
9
4i 4-Methoxyphenyl(1i)
4j 3,4-Dimethoxyphenyl(1j)
4k 3,4,5-Trimethoxyphenyl(1k)
4l 4-Hydroxy-3-nitrophenyl(1l)
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
10
10
10
10
10
10
10
8
10
11
12
13
14
7j
7k
7l
4m Benzo[d][1, 3]dioxol-5-yl(1m) 3a
7m
4n Thien-2-yl(1n)
3a
3b
3b
3b
3b
3b
3b
3b
3b
3b
3b
7n
aReagents and conditions: DMF (2.0 mL), 150oC, MW; b Isolated yield.
4o 2-Chlorophenyl(1b)
4p 2,4-Dichlorophenyl(1c)
4q 4-Fluorophenyl(1d)
4r 4-Bromophenyl(1e)
4s 4-Nitrophenyl(1f)
To study the applicational scope of this reaction,
benzo[h]naphtho[2,3-a]acridine- 15,16(5H,14H)-dione
were further employed to react with benzene-1,2-diamine 6a
under microwave irradiation. After several solvents were
screened, DMF was found to be the most suitable solvent for
4
8
8
4t 4-Tolyl(1h)
10
10
10
10
10
10
this
condensation
to
afford
quinoxaline-fused
benzo[h]naphtho[2,3-a]acridine 7 in excellent yields (81-
90%) (Table 3) (Scheme 3). The new extended angular fused
aza-heterocycles, such as cctocyclic and nonacyclic-fused
benzo[h]naphtho[2,3-a]acridines, were generated in high
yields when the naphthalene-2,3-diamine 6b was used as an
ortho-diamine component under similar condition. This
conversion can be finished within 20 min in this solvent at
150oC. It should be mentioned that the resulting quinoxaline-
containing multiheterocycles would be endowed with many
4u 4-Methoxyphenyl(1i)
4v 4-Dimethylaminophenyl(1o)
4w 3,4-Dimethoxyphenyl(1j)
4x 3,4,5-Trimethoxyphenyl(1k)
4y Benzo[d][1, 3]dioxol-5-yl(1m) 3b
aReagents and conditions: HOAc (1.5 mL), 120oC, MW; bmin; c Isolated yield.
significant
pharmacological
properties,
such
as
15,16(5H,14H)-dione in good yields (74-87%) and excellent
selectivities (Table 1, entries 15-25). For all these cases, the
reaction proceeded rapidly to completion within 8-10 min.
The present protocol provides a new, straightforward, and
effective pathway to construct benzo[h]naphtho[2,3-
a]acridine derivatives.
antiproliferatives, antimalarial, antitumor, antiamoebic, anti-
Mycobacterium tuberculosis agents, and CB2 receptor
antagonists [14].
Besides a high efficiency in the formation of multiple bonds
as a domino process, this reaction has the following advantages:
O
Ar
N
N
Ar
H2N
H2N
O
DMF, MW
150 oC
N
+
N
6
4
7
Scheme 3. Thesynthesis ofquinoxaline-fused benzo[h]naphtho[2,3-a]acridine.

404 Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5
Wang et al.
(1) the starting materials are readily available and the reagents
are very cheap; (2) the reaction proceeds smoothly under very
mild conditions without introducing strong acid, base or metal
catalyst; (3) the environmentally friendly process in which
water is the major by-product without additional use of organic
solvent during reaction process; (4) the convenient work-up
which only needs simple filtration since the products directly
precipitate out after the reaction is finished [15, 16] and when its
mixtures are diluted with cold water; and (5) the high
regioselectivity in which the reactions generated naphthoacri-
dine with ortho-diketone unit that serve as important building
blocks. The novelty of the present multicomponent domino
reaction is shown by the fact that multiple chemical bonds’
breaking and forming were simultaneously achieved in an
intermolecular manner and in a one-pot operation.
attracted by the amino group (-NH2) to give intermediate C
which is then converted into the naphthoacridines via
dehydration and isomerization steps [10f]. The synthesizing
naphthoacridines was further subjected with ortho-diamines to
give final extended angular fused aza-heterocycles 7 via
dehydration and dehydrogenation processes.
CONCLUSIONS
In summary, a new multicomponent domino reaction
have been established to afford benzo[h]naphtho[2,3-
a]acridine-15,16(5H,14H)-diones that serve as versatile
building blocks. The reactions showed high regioselectivity
and a broad scopes of substrates which can employ a wide
range of common commercial starting materials. A new
mechanism has been proposed to explain the reaction
process and regioselectivity. The resulting benzoquinoline
products have been successfully converted into
benzoquinoxaline-fused benzoquinolines by reacting with
benzene-1,2-diamine under microwave irradiation.
On the basis of all the above results, a possible mechanism
has been proposed for the formations of naphthoacridines and
its derivatives as shown in Scheme 4. The formation of 4
involves a ring closure cascade process that consists of initial
condensation, intermolecular Michael addition (A to B), intra-
molecular nucleophilic cyclization (B to C) and dehydration (C
to D) (Scheme 4). The intermediate B favors formation of
intramolecular hydrogen bond between carbonyl group
(position a) and ortho-hydroxyl group (position b), in which
enolization of hydroxyl group was further enhanced. During this
process, the carbonyl group (position c) would be easily
EXPERIMENTAL SECTION
General
Microwave irradiation was carried out with Biotage from
Personal Chemistry, Uppsala, Sweden. Melting points were
H
O
Ar
O
O
O
c
Ar
O
O
b
3
b
a
Ar
a
H2N
c
+
OH
H2N
O
OH
H
O
2
1
A
B
H
O
Ar
O
Ar
OH
Ar
N
O
O
O
-H2O
N
H
N
H
OH
4
D
C
H2N
H2N
N
Ar
6
N
-H2O
-2H
N
7
Scheme 4. The reasonable mechanism for the formation of products 4 and 7.

Microwave-Assisted Multicomponent Reactions
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5 405
determined in open capillaries and were uncorrected. IR
spectra were taken on a FT-IR-Tensor 27 spectrometer in
14-(2,4-Dichlorophenyl)dibenzo[a,h]acridine-12,13(7H,14
H)-dione (4c)
1
KBr pellets and reported in cm-1. H NMR spectra were
m.p.:ꢁ 269-271oC; IR (KBr, ꢀ, cm-1): 3285.5, 3049.5,
1580.1, 1513.6, 1475.3, 1386.6, 1041.2, 905.3, 802.1, 667.8;
1H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.50 (s, 1H,
NH), 8.51 (d, J = 8.0 Hz, 1H, ArH), 8.16 (d, J = 8.8 Hz, 1H,
ArH), 8.02-8.00 (m, 1H, ArH), 7.96-7.92 (m, 2H, ArH), 7.89
(d, J = 8.0 Hz, 1H, ArH), 7.85-7.83 (m, 1H, ArH), 7.71 (t, J
= 7.6 Hz, 1H, ArH), 7.54-7.50 (m, 1H, ArH), 7.44-7.40 (m,
3H, ArH), 7.22 (dd, J1 = 8.4 Hz, J2 = 2.4 Hz, 1H, ArH), 6.22
(s, 1H, CH). HRMS (ESI): m/z calcd for C27H16Cl2NO2:
456.0553 [M+H]+, found: 456.0560.
measured on a Bruker DPX 400 MHz spectrometer in CDCl3
or DMSO-d6 (100 MHz, 13C NMR) with chemical shift (ꢀ)
given in ppm relative to TMS as internal standard. HRMS
(ESI) was determined by using microTOF-QꢀꢁHRMS/MS
instrument (BRUKER)ꢂ X-Ray crystallographic analysis
was performed with a Siemens SMART CCD and a Siemens
P4 diffractometer.
Typical procedure for the synthesis of benzo[h]naphtho
[2,3-a]acridine-15,16(5H,14H)-diones 4 (4b as an example):
In
a
10-mL Initiator reaction vial, 2-hydroxy-1,4-
naphthoquinone 2 (1.0 mmol), 2-chlorobenzaldehyde 1b (1.0
mmol), naphthalen-2-amine 3 (1.0 mmol) and AcOH (1.5
mL) were mixed and then capped. The mixture was
irradiated for a given time at 120oC under microwave
irradiation (initial power 100 W and maximum power 250
W). Upon completion, monitored by TLC, the reaction
mixture was cooled to room temperature and washed with 2
mL 95% EtOH, filtered to give the crude products, which
were further purified by recrystallization from 95% EtOH to
afford the desired pure 4b.
14-(4-Fluorophenyl)dibenzo[a,h]acridine-12,13(7H,14H)-
dione (4d)
m.p.: >300oC; IR (KBr, ꢀ, cm-1): 3320.1, 3051.5, 1603.4,
1523.9, 1508.0, 1345.5, 1052.4, 826.0, 839.6, 762.7, 676.7,
1
556.8; H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.51 (s,
1H, NH), 8.46 (d, J = 8.0 Hz, 1H, ArH), 8.05 (d, J = 8.4 Hz,
1H, ArH), 8.00 (d, J = 8.0 Hz, 1H, ArH), 7.95-7.84 (m, 4H,
ArH), 7.69 (t, J = 7.6 Hz, 1H, ArH), 7.52-7.49 (m, 1H, ArH),
7.44-7.40 (m, 1H, ArH), 7.36-7.33 (m, 2H, ArH), 6.99 (t, J =
7.2 Hz, 2H, ArH), 6.05 (s, 1H, CH). HRMS (ESI): m/z calcd
for C27H17FNO2: 406.1238 [M+H]+, found: 406.1257.
Typical procedure for the synthesis of benzo[c]phena-
zine[2,1-b]quinolines 7 (7a as an example): In a 10-mL
Initiator reaction vial, 14-(4-Chlorophenyl)dibenzo[a,h]acri-
dine-12,13(7H,14H)-dione 4a, benzene-1,2-diamine 6a (1.0
mmol) and DMF (1.5 mL) were mixed and then capped. The
mixture was irradiated for a given time at 150oC under
microwave irradiation. Upon completion, monitored by
TLC, the reaction mixture was cooled to room temperature
and washed with 2 mL 95% EtOH, filtered to give the crude
products, which were further purified by recrystallization
from 1:1 mixture of MeOH and DMF to afford the desired
pure 7a.
14-(4-Bromophenyl)dibenzo[a,h]acridine-12,13(7H,14H)-
dione (4e)
m.p.:ꢁ>300oC; IR (KBr, ꢀ, cm-1): 3310.6, 3049.5, 1580.1,
1513.6, 1475.3, 1386.6, 1041.2, 905.3, 802.1, 667.8; 1H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.51 (s, 1H, NH),
8.46 (d, J = 7.6 Hz, 1H, ArH), 8.03-8.01 (m, 2H, ArH), 7.96-
7.89 (m, 3H, ArH), 7.70 (t, J = 7.6 Hz, 1H, ArH), 7.52-7.48
(m, 1H, ArH), 7.44-7.40 (m, 1H, ArH), 7.38-7.35 (m, 2H,
ArH), 7.29-7.27 (m, 2H, ArH), 6.03 (s, 1H, CH). HRMS
(ESI): m/z calcd for C27H17BrNO2: 466.0438 [M+H]+, found:
466.0453.
14-(4-Chlorophenyl)dibenzo[a,h]acridine-12,13(7H,14H)-
dione (4a)
m.p.:ꢁ>300oC; IR (KBr, ꢀ, cm-1): 3401.2, 3050.6, 1589.2,
1515.2, 1500.3, 1402.6, 1051.4, 822.0, 801.8, 758.3, 670.5,
14-(4-Nitrophenyl)dibenzo[a,h]acridine-12,13(7H,14H)-di
one (4f)
1
587.7; H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.52 (s,
m.p.:ꢁ ꢃ300oC; IR (KBr, ꢀ, cm-1): 3288.4, 3052.7,
1608.9, 1501.4, 1420.5, 1333.9, 1315.0, 1260.4, 1199.2,
1172.5, 1120.0, 789.7; 1H NMR (400MHz, DMSO-d6,
25oC): ꢀ = 10.60 (s, 1H, NH), 8.50 (d, J = 7.6 Hz, 1H, ArH),
8.07-7.88 (m, 8H, ArH), 7.71 (t, J = 7.2 Hz, 1H, ArH), 7.62
(d, J = 8.4 Hz, 2H, ArH), 7.53-7.49 (m, 1H, ArH), 7.45-7.41
(m, 1H, ArH), 6.20 (s, 1H, CH). HRMS (ESI): m/z calcd for
C27H17N2O4: 433.1183 [M+H]+, found: 433.1201.
1H, NH), 8.47 (d, J = 8.0 Hz, 1H, ArH), 8.05-8.00 (m, 2H,
ArH), 7.96-7.85 (m, 4H, ArH), 7.70 (t, J = 7.6 Hz, 1H, ArH),
7.53-7.49 (m, 1H, ArH), 7.45-7.41 (m, 1H, ArH), 7.35-7.33
(m, 2H, ArH), 7.24-7.22 (m, 2H, ArH), 6.05 (s, 1H, CH).
HRMS (ESI): m/z calcd for C27H17ClNO2: 422.0943
[M+H]+, found: 422.0950.
14-(2-Chlorophenyl)dibenzo[a,h]acridine-12,13(7H,14H)-
dione (4b)
14-Phenyldibenzo[a,h]acridine-12,13(7H,14H)-dione (4g)
m.p.: 278-280oC; IR (KBr, ꢀ, cm-1): 3305.6, 3048.7,
1580.1, 1520.4, 1489.6, 1400.9, 1060.8, 811.1, 758.3, 625.6;
1H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.52 (s, 1H,
NH), 8.52 (d, J = 8.0 Hz, 1H, ArH), 8.24 (d, J = 8.4 Hz, 1H,
ArH), 8.02-8.00 (m, 1H, ArH), 7.97-7.91 (m, 2H, ArH),
7.89-7.84 (m, 2H, ArH), 7.73-7.70 (m, 1H, ArH), 7.54-7.50
(m, 1H, ArH), 7.43-7.41 (m, 2H, ArH), 7.30-7.28 (m, 1H,
ArH), 7.15-7.11 (m, 1H, ArH), 7.08-7.04 (m, 1H, ArH), 6.25
(s, 1H, CH). HRMS (ESI): m/z calcd for C27H17ClNO2:
422.0943 [M+H]+, found: 422.0955.
m.p.:ꢁ >300oC; IR (KBr, ꢀ, cm-1): 3305, 3050, 1698,
1541, 1524, 1347, 1218, 1118, 1053, 726; 1H NMR
(400MHz, DMSO-d6, 25oC): ꢀ = 10.49 (s, 1H, NH), 8.46 (d,
J = 8.0 Hz, 1H, ArH), 8.06 (d, J = 8.4 Hz, 1H, ArH), 8.00
(dd, J1 = 7.6 Hz, J2 = 1.2 Hz, 1H, ArH), 7.95-7.84 (m, 4H,
ArH), 7.69 (t, J = 7.6 Hz, 1H, ArH), 7.52-7.50 (m, 1H, ArH),
7.41 (t, J = 7.2 Hz, 1H, ArH), 7.34 (s, 1H, ArH), 7.32 (s, 1H,
ArH), 7.18-7.14 (m, 2H, ArH), 7.03 (t, J = 7.2 Hz, 1H, ArH),
6.04 (s, 1H, CH). HRMS (ESI): m/z calcd for C27H18NO2:
388.1333 [M+H]+, found: 388.1362.

406 Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5
Wang et al.
J = 8.8 Hz, 1H, ArH), 8.05 (d, J = 8.4 Hz, 1H, ArH), 8.01-
7.90 (m, 4H, ArH), 7.86 (d, J = 8.8 Hz, 1H, ArH), 7.79 (d, J
= 2.0 Hz, 1H, ArH), 7.69 (t, J = 7.6 Hz, 1H, ArH), 7.54-7.49
(m, 2H, ArH), 7.43 (t, J = 7.6 Hz, 1H, ArH), 6.97(d, J = 8.4
Hz, 1H, ArH), 6.05 (s, 1H, CH). HRMS (ESI): m/z calcd for
C27H17N2O5: 449.1132 [M+H]+, found: 449.1160.
14-p-Tolyldibenzo[a,h]acridine-12,13(7H,14H)-dione (4h)
m.p.:ꢁ 289-291oC; IR (KBr, ꢀ, cm-1): 3355.1, 3051.6,
2867.8, 1681.3, 1561.0, 1524.4, 1460.9, 1416.5, 1259.8,
1
1038.1, 739.8; H NMR (400MHz, DMSO-d6, 25oC): ꢀ =
10.46 (s, 1H, NH), 8.45 (d, J = 8.0 Hz, 1H, ArH), 8.04 (d, J
= 8.4 Hz, 1H, ArH), 7.99 (d, J = 7.6 Hz, 1H, ArH), 7.93-7.83
(m, 4H, ArH), 7.69 (t, J = 7.6 Hz, 1H, ArH), 7.51-7.47 (m,
1H, ArH), 7.43-7.39 (m, 1H, ArH), 7.20-7.18 (m, 2H, ArH),
6.97-6.94 (m, 2H, ArH), 5.99 (s, 1H, CH) 2.11 (s, 3H, CH3).
HRMS (ESI): m/z calcd for C28H20NO2: 402.1489 [M+H]+,
found: 402.1499.
14-(Benzo[d][1,3]dioxol-5-yl)dibenzo[a,h]acridine-12,13(7
H,14H)-dione (4m)
m.p.: >300oC; IR (KBr, ꢀ, cm-1): 3388.6, 3023.1, 2940.6,
1611.8, 1534.7, 1583.5, 1525.6, 1356.6, 1224.7, 1023.4,
841.3, 768.2, 754.1; 1H NMR (400MHz, DMSO-d6, 25oC): ꢀ
= 10.47 (s, 1H, NH), 8.45 (d, J = 8.0 Hz, 1H, ArH), 8.07 (d,
J = 8.0 Hz, 1H, ArH), 8.01 (dd, J1 = 7.6 Hz, J2 = 0.8 Hz, 1H,
ArH), 7.94-7.89 (m, 3H, ArH), 7.84 (d, J = 8.8 Hz, 1H,
ArH), 7.69 (t, J = 7.6 Hz, 1H, ArH), 7.54-7.49 (m, 1H, ArH),
7.45-7.41 (m, 1H, ArH), 6.88 (d, J = 2.0 Hz, 1H, ArH), 6.73-
6.67 (m, 2H, ArH), 5.86 (s, 1H, CH) 5.85 (d, J = 8.0 Hz, 2H,
CH2). HRMS (ESI): m/z calcd for C28H18NO4: 432.1231
[M+H]+, found: 432.1253.
14-(4-Methoxyphenyl)dibenzo[a,h]acridine-12,13(7H,14H)
-dione (4i)
m.p.:ꢁ 291-293oC; IR (KBr, ꢀ, cm-1): 3356.1, 3050.9,
1603.5, 1522.9, 1543.0, 1343.3, 1240.4, 1032.5, 841.5,
768.7, 753.2, 676.8; 1H NMR (400MHz, DMSO-d6, 25oC): ꢀ
= 10.47 (s, 1H, NH), 8.45 (d, J = 8.0 Hz, 1H, ArH), 8.05 (d,
J = 8.4 Hz, 1H, ArH), 7.99 (d, J = 7.6 Hz, 1H, ArH), 7.93-
7.83 (m, 4H, ArH), 7.68 (t, J = 7.6 Hz, 1H, ArH), 7.51-7.48
(m, 1H, ArH), 7.43-7.39 (m, 1H, ArH), 7.23-7.21 (m, 2H,
ArH), 6.73-6.71 (m, 2H, ArH), 5.98 (s, 1H, CH) 3.56 (s, 3H,
CH3). HRMS (ESI): m/z calcd for C28H20NO3: 418.1438
[M+H]+, found: 418.1460.
14-(Thiophen-2-yl)dibenzo[a,h]acridine-12,13(7H,14H)-di-
one (4n)
m.p.: 269-271oC; IR (KBr, ꢀ, cm-1): 3326.2, 3045.3,
1698.6, 1580.7, 1500.5, 1491.8, 1451.9, 1440.4, 1402.9,
1230.4, 1116.6, 877.9; 1H NMR (400MHz, DMSO-d6,
25oC): ꢀ = 10.61 (s, 1H, NH), 8.45 (d, J = 7.6 Hz, 1H, ArH),
8.11 (d, J = 8.8 Hz, 1H, ArH), 8.03 (dd, J1 = 7.6 Hz, J2 = 0.8
Hz, 1H, ArH), 7.97-7.91 (m, 3H, ArH), 7.82 (d, J = 8.8 Hz,
1H, ArH), 7.71 (t, J = 7.6 Hz, 1H, ArH), 7.59-7.55 (m, 1H,
ArH), 7.48-7.45 (m, 1H, ArH), 7.16 (dd, J1 = 7.2 Hz, J2 = 1.2
Hz, 1H, ArH), 6.77-6.74 (m, 2H, ArH), 6.35 (s, 1H, CH).
HRMS (ESI): m/z calcd for C25H16NO2S: 394.0897 [M+H]+,
found: 394.0919.
14-(3,4-Dimethoxyphenyl)dibenzo[a,h]acridine-12,13(7H,
14H)-dione (4j)
m.p.: 271-273oC; IR (KBr, ꢀ, cm-1): 3401.3 3049.1,
2950.0, 1606.8, 1545.5, 1522.6, 1507.6, 1344.7, 1239.1,
1
1032.9, 840.8, 761.2, 753.4; H NMR (400MHz, DMSO-d6,
25oC): ꢀ = 10.48 (s, 1H, NH), 8.44 (d, J = 8.0 Hz, 1H, ArH),
8.09 (d, J = 8.4 Hz, 1H, ArH), 8.00 (d, J = 7.6 Hz, 1H, ArH),
7.94-7.88 (m, 3H, ArH), 7.87 (d, J = 8.4 Hz, 1H, ArH), 7.69
(t, J = 7.6 Hz, 1H, ArH), 7.52-7.49 (m, 1H, ArH), 7.44-7.40
(m, 1H, ArH), 7.07 (d, J = 1.6 Hz, 1H, ArH), 6.69 (d, J = 8.4
Hz, 1H, ArH), 6.63-6.60 (m, 1H, ArH), 5.99 (s, 1H, CH)
3.66 (s, 3H, CH3), 3.58 (s, 3H, CH3). HRMS (ESI): m/z
calcd for C29H22NO4: 448.1544 [M+H]+, found: 448.1558.
14-(2-Chlorophenyl)benzo[h]naphtho[2,3-a]acridine-15,
16(5H,14H)-dione (4o)
m.p.: 283-285oC; IR (KBr, ꢀ, cm-1): 3320, 3051, 1670,
1603, 1580, 1564, 1502, 1458, 1449, 1252, 1170, 873, 725;
1H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.51 (s, 1H,
NH), 8.84 (s, 1H, ArH), 8.54-8.52 (m, 2H, ArH), 8.09 (d, J =
8.8 Hz, 1H, ArH), 8.03-7.93 (m, 4H, ArH), 7.86 (d, J = 9.2
Hz, 1H, ArH), 7.71 (t, J = 7.2 Hz, 1H, ArH), 7.54-7.46 (m,
3H, ArH), 7.30 (dd, J1 = 7.6 Hz, J2 = 1.2 Hz, 2H, ArH),
7.13-7.10 (m, 2H, ArH), 7.05-7.01 (m, 2H, ArH), 6.37 (s,
1H, CH). HRMS (ESI): m/z calcd for C31H19ClNO2:
472.1099 [M+H]+, found: 472.1118.
14-(3,4,5-Trimethoxyphenyl)dibenzo[a,h]acridine-12,13(7
H,14H)-dione (4k)
m.p.: 282-284oC; IR (KBr, ꢀ, cm-1): 3403.2, 3038.1,
2940.7, 1589.5, 1523.6, 1528.2, 1507.7, 1346.3, 1238.2,
1
1039.1, 840.0, 767.6, 757.4; H NMR (400MHz, DMSO-d6,
25oC): ꢀ = 10.53 (s, 1H, NH), 8.45 (d, J = 7.6 Hz, 1H, ArH),
8.13 (d, J = 8.4 Hz, 1H, ArH), 8.01 (dd, J1 = 7.6 Hz, J2 = 1.2
Hz, 1H, ArH), 7.96-7.90 (m, 3H, ArH), 7.84 (d, J = 8.8 Hz,
1H, ArH), 7.69 (t, J = 7.6 Hz, 1H, ArH), 7.55-7.51 (m, 1H,
ArH), 7.45-7.42 (m, 1H, ArH), 6.59 (s, 2H, ArH), 6.01 (s,
1H, CH) 3.61 (s, 6H, CH3), 3.51 (s, 3H, CH3). HRMS (ESI):
m/z calcd for C30H24NO5: 478.1649 [M+H]+, found:
478.1674.
14-(2,4-Dichlorophenyl)benzo[h]naphtho[2,3-a]acridine-
15,16(5H,14H)-dione (4p)
m.p.: 276-278oC; IR (KBr, ꢀ, cm-1): 3314, 3071, 1698,
1609, 1588, 1557, 1504, 1469, 1460, 1257, 1232, 877, 739;
1H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.53 (s, 1H,
NH), 8.77 (s, 1H, ArH), 8.53-8.52 (m, 2H, ArH), 8.10 (d, J =
9.2 Hz, 1H, ArH), 8.04-7.93 (m, 4H, ArH), 7.87 (d, J = 9.2
Hz, 1H, ArH), 7.72 (t, J = 7.6 Hz, 1H, ArH), 7.53-7.49 (m,
3H, ArH), 7.45 (d, J = 1.6 Hz, 1H, ArH), 7.21 (dd, J1 = 8.4
Hz, J2 = 2.0 Hz, 1H, ArH), 6.35 (s, 1H, CH). HRMS (ESI):
14-(4-Hydroxy-3-nitrophenyl)dibenzo[a,h]acridine-12,13
(7H,14H)-dione (4l)
m.p.: 298-300oC; IR (KBr, ꢀ, cm-1): 3430.6, 3360.6,
3054.7, 1622.9, 1523.1, 1418.6, 1345.7, 1320.9, 1268.4,
1
1236.3, 1191.1, 1134.0, 765.9; H NMR (400MHz, DMSO-
d6, 25oC): ꢀ = 10.75 (s, 1H, OH), 10.45 (s, 1H, NH), 8.46 (d,

Microwave-Assisted Multicomponent Reactions
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5 407
m/z calcd for C31H18Cl2NO2: 506.0710 [M+H]+, found:
506.0729.
8.69 (s, 1H, ArH), 8.53 (s, 1H, ArH), 8.47 (d, J = 8.0 Hz,
1H, ArH), 8.14-8.08 (m, 2H, ArH), 8.03-8.00 (m, 2H, ArH),
7.94-7.90 (m, 1H, ArH), 7.87 (d, J = 9.2 Hz, 1H, ArH), 7.69
(t, J = 7.6 Hz, 1H, ArH), 7.50-7.47 (m, 2H, ArH), 7.35 (d, J
= 8.4 Hz, 2H, ArH), 6.71 (d, J = 8.8 Hz, 2H, ArH), 6.16 (s,
1H, CH), 3.58 (s, 3H, CH3). HRMS (ESI): m/z calcd for
C32H22NO3: 468.1595 [M+H]+, found: 468.1611.
14-(4-Fluorophenyl)benzo[h]naphtho[2,3-a]acridine-15,16
(5H,14H)-dione (4q)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3318, 3051, 1694, 1585,
1504, 1461, 1257, 1232, 889; 1H NMR (400MHz, DMSO-d6,
25oC): ꢀ = 10.54 (s, 1H, NH), 8.70 (s, 1H, ArH), 8.55 (s, 1H,
ArH), 8.49 (d, J = 8.0 Hz, 1H, ArH), 8.16-8.11 (m, 2H,
ArH), 8.05-8.01 (m, 2H, ArH), 7.93 (t, J = 7.2 Hz, 1H, ArH),
7.89 (d, J = 9.2 Hz, 1H, ArH), 7.71 (t, J = 7.6 Hz, 1H, ArH),
7.51-7.47 (m, 4H, ArH), 6.98 (t, J = 8.8 Hz, 2H, ArH), 6.23
(s, 1H, CH). HRMS (ESI): m/z calcd for C31H19FNO2:
456.1395 [M+H]+, found: 456.1416.
14-(4-(Dimethylamino)phenyl)benzo[h]naphtho[2,3-a]ac-
ridine-15,16(5H,14H)-dione (4v)
m.p.: 286-288oC; IR (KBr, ꢁ, cm-1): 3306, 3061, 1692,
1
1608, 1585, 1502, 1480, 1460, 1257, 874, 812, 738; H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.45 (s, 1H, NH),
8.69 (s, 1H, ArH), 8.53 (s, 1H, ArH), 8.46 (d, J = 8.0 Hz,
1H, ArH), 8.13-8.07 (m, 2H, ArH), 8.04-8.00 (m, 2H, ArH),
7.92 (t, J = 7.6 Hz, 1H, ArH), 7.85 (d, J = 9.2 Hz, 1H, ArH),
7.69 (t, J = 7.6 Hz, 1H, ArH), 7.51-7.45 (m, 2H, ArH), 7.24
(d, J = 8.8 Hz, 2H, ArH), 6.50 (d, J = 8.8 Hz, 2H, ArH), 6.09
(s, 1H, CH), 2.70 (s, 6H, CH3). HRMS (ESI): m/z calcd for
C33H25N2O2: 481.1911 [M+H]+, found: 481.1929.
14-(4-Bromophenyl)benzo[h]naphtho[2,3-a]acridine-15,16
(5H,14H)-dione (4r)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3330, 2912, 1585, 1504,
1482, 1469, 1462, 1255, 1011, 911, 778; 1H NMR (400MHz,
DMSO-d6, 25oC): ꢀ = 10.56 (s, 1H, NH), 8.69 (s, 1H, ArH),
8.56 (s, 1H, ArH), 8.49 (d, J = 8.0 Hz, 1H, ArH), 8.16-8.12
(m, 2H, ArH), 8.05-8.01 (m, 2H, ArH), 7.94 (t, J = 7.2 Hz,
1H, ArH), 7.88 (d, J = 8.8 Hz, 1H, ArH), 7.71 (t, J = 7.2 Hz,
1H, ArH), 7.50-7.49 (m, 2H, ArH), 7.42 (d, J = 8.4 Hz, 2H,
ArH), 7.36 (d, J = 8.4 Hz, 2H, ArH), 6.20 (s, 1H, CH).
HRMS (ESI): m/z calcd for C31H19BrNO2: 516.0594
[M+H]+, found: 516.0611.
14-(3,4-Dimethoxyphenyl)benzo[h]naphtho[2,3-a]acridine- 15,
16(5H,14H)-dione (4w)
m.p.: 274-276oC; IR (KBr, ꢁ, cm-1): 3327, 3062, 2930,
1692, 1587, 1504, 1481, 1470, 1462, 1264, 1238, 1140,
1
1029, 871, 737; H NMR (400MHz, DMSO-d6, 25oC): ꢀ =
10.50 (s, 1H, NH), 8.76 (s, 1H, ArH), 8.54 (s, 1H, ArH),
8.47 (d, J = 7.6 Hz, 1H, ArH), 8.16 (d, J = 7.2 Hz, 1H, ArH),
8.10 (d, J = 8.8 Hz, 1H, ArH), 8.04-8.01 (m, 2H, ArH), 7.94-
7.91 (m, 1H, ArH), 7.87 (d, J = 8.8 Hz, 1H, ArH), 7.72-7.68
(m, 1H, ArH), 7.50-7.47 (m, 2H, ArH), 7.29 (d, J = 2.0 Hz,
1H, ArH), 6.74-6.67 (m, 2H, ArH), 6.53 (s, 1H, CH), 3.72 (s,
3H, CH3), 3.55 (s, 3H, CH3). HRMS (ESI): m/z calcd for
C33H24NO4: 498.1700 [M+H]+, found: 498.1721.
14-(4-Nitrophenyl)benzo[h]naphtho[2,3-a]acridine-15,16
(5H,14H)-dione (4s)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3313, 3044, 1698, 1608,
1588, 1557, 1504, 1479, 1469, 1460, 1257, 877, 738, 631; 1H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.62 (s, 1H, NH),
8.70 (s, 1H, ArH), 8.56 (s, 1H, ArH), 8.51 (d, J = 7.6 Hz,
1H, ArH), 8.16-8.14 (m, 2H, ArH), 8.06-8.02 (m, 4H, ArH),
7.97-7.90 (m, 2H, ArH), 7.76 (d, J = 8.8 Hz, 2H, ArH), 7.72
(t, J = 7.6 Hz, 1H, ArH), 7.52-7.46 (m, 2H, ArH), 6.37 (s,
1H, CH). HRMS (ESI): m/z calcd for C31H19N2O4: 483.1340
[M+H]+, found: 483.1364.
14-(3,4,5-Trimethoxyphenyl)benzo[h]naphtho[2,3-a]acri-
dine-15,16(5H,14H)-dione (4x)
m.p.: 290-293oC; IR (KBr, ꢁ, cm-1): 3321, 3047, 1692,
1
1587, 1503, 1481, 1469, 1461, 1417, 1251, 1124, 871; H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.55 (s, 1H, NH),
8.82 (s, 1H, ArH), 8.55 (s, 1H, ArH), 8.48 (d, J = 8.0 Hz,
1H, ArH), 8.21 (d, J = 8.4 Hz, 1H, ArH), 8.11 (d, J = 9.2 Hz,
1H, ArH), 8.03 (m, 2H, ArH), 7.94-7.86 (m, 2H, ArH), 7.70
(t, J = 7.6 Hz, 1H, ArH), 7.53-7.46 (m, 2H, ArH), 6.77 (s,
2H, ArH), 6.18 (s, 1H, CH), 3.64 (s, 6H, CH3), 3.48 (s, 3H,
CH3). HRMS (ESI): m/z calcd for C34H26NO5: 528.1806
[M+H]+, found: 528.1819.
14-p-Tolylbenzo[h]naphtho[2,3-a]acridine-15,16(5H,14H)-
dione (4t)
m.p.: 292-294oC; IR (KBr, ꢁ, cm-1): 3335, 3048, 1585,
1
1504, 1481, 1470, 1461, 1424, 1255, 870, 737; H NMR
(400MHz, DMSO-d6, 25oC): ꢀ = 10.50 (s, 1H, NH), 8.68 (s,
1H, ArH), 8.54 (s, 1H, ArH), 8.47 (d, J = 8.0 Hz, 1H, ArH),
8.14-8.09 (m, 2H, ArH), 7.95-7.91 (m, 1H, ArH), 7.87 (d, J
= 8.8 Hz, 1H, ArH), 7.70 (t, J = 7.2 Hz, 1H, ArH), 7.50-7.47
(m, 2H, ArH), 7.33 (d, J = 8.0 Hz, 2H, ArH), 6.95 (d, J = 8.0
Hz, 2H, ArH), 6.17 (s, 1H, CH), 2.09 (s, 3H, CH3). HRMS
(ESI): m/z calcd for C32H22NO2: 452.1646 [M+H]+, found:
452.1671.
14-(Benzo[d][1,3]dioxol-5-yl)benzo[h]naphtho[2,3-a]acri-
dine-15,16(5H,14H)-dione (4y)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3320, 3006, 2920, 1684,
1580, 1524, 1477, 1465, 1455, 1259, 1235, 1144, 1010, 872,
739; 1H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.50 (s, 1H,
NH), 8.72 (s, 1H, ArH), 8.54 (s, 1H, ArH), 8.47 (d, J = 7.6
Hz, 1H, ArH), 8.17-8.15 (m, 1H, ArH), 8.12 (d, J = 9.2 Hz,
1H, ArH), 8.05-8.01 (m, 2H, ArH), 7.94-7.90 (m, 1H, ArH),
7.87 (d, J = 9.2 Hz, 1H, ArH), 7.70 (t, J = 7.6 Hz, 1H, ArH),
7.51-7.48 (m, 2H, ArH), 7.04 (d, J = 1.6 Hz, 1H, ArH), 6.86-
6.84 (m, 1H, ArH), 6.68 (d, J = 8.0 Hz, 1H, ArH), 6.15 (s,
14-(4-Methoxyphenyl)benzo[h]naphtho[2,3-a]acridine-15,
16(5H,14H)-dione (4u)
m.p.: 289-291oC; IR (KBr, ꢁ, cm-1): 3324, 1586, 1504,
1480, 1469, 1460, 1417, 1256, 1177, 1029, 870, 707; H
1
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.49 (s, 1H, NH),

408 Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5
Wang et al.
1H, CH), 5.83 (d, J = 10.0 Hz, 1H, CH2). HRMS (ESI): m/z
calcd for C32H20NO4: 482.1387 [M+H]+, found: 482.1398.
8.29-8.18 (m, 3H, ArH), 8.07 (d, J =7.6 Hz,1H, ArH), 8.00-
7.82 (m, 4H, ArH),7.66 (d, J = 8.4 Hz, 1H, ArH), 7.60 (t, J =
7.6 Hz, 1H, ArH), 7.28-7.21 (m, 2H, ArH), 7.22 (d, J = 8.0
Hz, 1H, ArH), 7.08 (d, J = 1.6 Hz, 1H, ArH), 6.86 (dd, J1 =
8.0 Hz, J2 = 1.2 Hz, 1H, ArH), 4.00 (s, 3H, CH3), 3.56 (s,
3H, CH3); HRMS (ESI): m/z calcd for C35H23N3O2:
518.1863 [M+H]+, found: 518.1891.
18-(4-Chlorophenyl)benzo[f](benzo[c]phenazine)[2,1-b] qui-
noline (7a)
m.p.: 279-281oC; IR (KBr, ꢁ, cm-1): 3051.8, 1603.4,
1523.9, 1508.0, 1345.5, 1052.4, 826.0, 839.6, 762.7, 676.7,
1
556.8; H NMR (400MHz, CDCl3, 25oC): ꢀ = 9.38 (d, J =
18-(3,4,5-Trimethoxyphenyl)benzo[f](benzo[c]phenazine)
[2,1-b]quinoline (7f)
8.0 Hz, 1H, ArH), 9.19 (d, J = 8.0 Hz,1H, ArH), 8.33-8.21
(m, 3H, ArH)ꢀ8.11 (d, J = 8.0 Hz, 1H, ArH), 8.01-7.87 (m,
4H, ArH), 7.73 (d, J = 8.0 Hz, 2H, ArH), 7.62 (t, J = 7.6 Hz,
1H, ArH), 7.55 (d, J = 9.2 Hz, 1H, ArH), 7.48 (d, J = 8.0Hz,
2H, ArH), 7.30-7.22 (m, 2H, ArH); HRMS (ESI): m/z calcd
for C33H18ClN3: 492.1262 [M+H]+, found: 492.1296.
m.p.: 290-292oC; IR (KBr, ꢁ, cm-1): 2990.9, 1581.3,
1517.8, 1503.5, 1352.4, 1234.0, 1126.9, 1011.5, 873.2,
767.6, 739.3; 1H NMR (400MHz, CDCl3, 25oC): ꢀ = 9.40 (d,
J = 8.0 Hz, 1H, ArH), 9.22 (d, J = 7.6 Hz, 1H, ArH), 8.32-
8.21 (m, 3H, ArH), 8.09 (dd, J1 = 8.0Hz, J2 =0.8 Hz, 1H,
ArH), 8.01-7.85 (m, 4H, ArH), 7.68 (d, J = 9.2 Hz, 1H,
ArH), 7.62 (t, J = 7.2 Hz, 1H, ArH), 7.39 (d, J = 8.4 Hz, 1H,
ArH), 7.33-7.29 (m, 1H, ArH), 6.78 (s, 2H, ArH), 3.99 (s,
3H, CH3), 3.56 (s, 6H, CH3); HRMS (ESI): m/z calcd for
C36H25N3O3: 548.1969 [M+H]+, found: 548.1989.
18-(2-Chlorophenyl)benzo[f](benzo[c]phenazine)[2,1-b]quino-
line (7b)
m.p.: 278-280oC; IR (KBr, ꢁ, cm-1): 3047.3, 2887.3,
1522.5, 1489.3, 1446.9, 1346.7, 1242.6, 1228.6, 1041.1,
1
941.1, 764.4, 676.4; H NMR (400MHz, CDCl3, 25oC): ꢀ =
9.54 (d, J = 8.0 Hz, 1H, ArH), 9.31 (d, J = 7.6 Hz, 1H, ArH),
8.31 (d, J = 8.8 Hz, 1H, ArH), 8.22 (d, J = 8.4 Hz, 1H, ArH),
8.11 ( d, J = 8.8 Hz, 1H, ArH), 7.94-7.85 (m, 3H, ArH),
7.79-7.71 (m, 3H, ArH), 7.65 (t, J = 7.2 HZ, 1H, ArH), 7.57-
7.53 (m, 2H, ArH), 7.51-7.47 (m, 1H, ArH), 7.30-7.27 (m,
2H, ArH), 7.23-7.21 (m, 1H, ArH); HRMS (ESI): m/z calcd
for C33H18ClN3: 492.1262 [M+H]+, found: 492.1351.
18-(4-Hydroxy-3-nitrophenyl)benzo[f](benzo[c]phenazine)[2,
1-b]quinoline (7g)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3257, 3021, 1589, 1516,
1
1501, 1351, 1238, H NMR (400MHz, CDCl3, 25oC): ꢀ =
9.45 (d, J = 7.2 Hz, 1H, ArH), 9.28 (d, J = 7.6 Hz, 1H, ArH),
8.25-8.22 (m, 2H, ArH), 8.09 (d, J = 9.2Hz, 1H, ArH), 8.04
(d, J = 2.0 Hz, 1H, ArH), 7.93-7.85 (m, 3H, ArH), 7.81-7.74
(m, 2H, ArH), 7.68 (t, J = 6.8 Hz, 1H, ArH), 7.62 (d, J = 7.6
Hz, 1H, ArH), 7.57-7.51 (m, 2H, ArH), 7.32 (d, J = 8.0 Hz,
1H, ArH), 7.62 (s, 1H, ArH); HRMS (ESI): m/z calcd for
C33H18N4O3: 519.1452 [M+H]+, found: 519.1473.
18-p-Tolyl benzo[f](benzo[c]phenazine)[2,1-b]quinoline (7c)
m.p.: 296-298oC; IR (KBr, ꢁ, cm-1): 3051.6, 2867.8,
1681.3, 1561.0, 1524.4, 1460.9, 1416.5, 1259.8, 1038.1,
739.8; 1H NMR (400MHz, CDCl3, 25oC): ꢀ = (d, J = 7.6 Hz,
1H, ArH), 9.28 (d, J = 7.2 Hz, 1H, ArH), 8.20 (d, J = 8.4 Hz,
1H, ArH), 8.09 (d, J = 8.8 Hz, 1H, ArH), 7.93-7.84 (m, 3H,
ArH), 7.77-7.73 (m, 1H, ArH), 7.67-7.62 (m, 2H, ArH),
7.51(t, J = 7.2 Hz, 1H, ArH), 7.44 (d, J = 8.0 Hz, 2H, ArH ),
7.29-7.24 (m, 3H, ArH), 7.20-7.16 (m, 1H, ArH), 2.69 (s,
3H, CH3); HRMS (ESI): m/z calcd for C34H21N3: 472.1808
[M+H]+, found: 472.1849.
18-(Benzo[d][1,3]dioxol-6-yl)benzo[f](benzo[c]phenazine)
[2,1-b]quinoline (7h)
m.p.: 168-171oC; IR (KBr, ꢁ, cm-1): 3051.8, 1513.6,
1400.2, 1355.7, 1323.6, 1248.9, 1024.9, 861.2, 799.5, 740.1;
1H NMR (400MHz, CDCl3, 25oC): ꢀ = 9.44 (d, J = 8.0 Hz,
1H, ArH), 9.26 (d, J = 8.0 Hz, 1H, ArH), 8.23-8.20 (m, 2H,
ArH), 8.07 (d, J = 8.8 Hz, 1H, ArH), 7.92-7.75 (m, 5H,
ArH), 7.71-7.67 (m, 1H, ArH), 7.54 (t, J = 7.6 Hz, 1H, ArH),
7.45 (d, J = 8.4 Hz, 1H, ArH), 7.29-7.25 (m, 1H, ArH), 7.09
(d, J = 8.0 Hz, 1H, ArH), 6.88 (s, 1H, ArH), 6.85 (dd, J1 =
8.0Hz, J2 = 1.2 Hz, 1H, ArH), 6.19 (s, 2H, CH2); HRMS
(ESI): m/z calcd for C34H19N3O2: 502.1550 [M+H]+, found:
502.1589.
18-(4-Methoxyphenyl)benzo[f](benzo[c]phenazine)[2,1-b]
quinoline (7d)
m.p.: 288-290oC; IR (KBr, ꢁ, cm-1): 3050.9, 1603.5,
1522.9, 1543.0, 1343.3, 1240.4, 1032.5, 841.5, 768.7, 753.2,
1
676.8; H NMR (400MHz, CDCl3, 25oC): ꢀ = 9.36 (d, J =
8.0 Hz, 1H, ArH), 9.18 (d, J = 7.6 Hz, 1H, ArH), 8.29-8.18
(m, 3H, ArH ), 8.08 (d, J = 7.2 Hz, 1H, ArH), 8.01-7.85 (m,
3H, ArH), 7.83 (t, J = 7.2 Hz, 1H, ArH), 7.61-7.57 (m, 2H,
ArH), 7.31-7.21 (m, 6H, ArH), 3.99 (s, 3H, CH3); HRMS
(ESI): m/z calcd for C34H21N3O: 488.1757 [M+H]+, found:
488.1792.
19-(4-Fluorophenyl)naphtho[2,3-f](benzo[c]phenazine)[2,
1-b]quinoline (7i)
m.p.: 289-291oC; IR (KBr, ꢁ, cm-1): 3054, 1517, 1346,
1318, 1054, 1011. 1H NMR (400MHz, DMSO-d6, 25oC): ꢀ =
9.51 (d, J = 8.0 Hz, 1H, ArH), 9.32 (d, J = 7.6 Hz, 1H, ArH),
8.35 (s, 1H, ArH ), 8.23 (d, J = 7.6 Hz, 1H, ArH), 8.14 (s,
1H, ArH ), 7.99 (d, J = 8.0 Hz, 1H, ArH), 7.84-7.77 (m, 3H,
ArH), 7.71-7.68 (m, 2H, ArH), 7.59-7.49 (m, 1H, ArH),
7.47-7.42 (m, 6H, ArH), 7.37 (d, J = 7.6 Hz, 1H, ArH);
HRMS (ESI): m/z calcd for C37H20FN3: 526.1715 [M+H]+,
found: 526.1699.
18-(3,4-Dimethoxyphenyl)benzo[f](benzo[c]phenazine)[2,
1-b]quinoline (7e)
m.p.: 295-297oC; IR (KBr, ꢁ, cm-1): 3051.5, 2901.7,
1600.7, 1510.3, 1529.9, 1341.4, 1238.6, 1033.5, 838.8,
1
764.2, 752.6, 677.7; H NMR (400MHz, CDCl3, 25oC): ꢀ =
9.36 (d, J = 7.6 Hz, 1H, ArH), 9.18(d, J = 7.6 Hz, 1H, ArH),

Microwave-Assisted Multicomponent Reactions
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5 409
8.36 (s, 1H, ArH), 8.21 (s, 1H, ArH), 8.15-8.13 (m, 2H,
ArH), 8.10-8.08 (m, 2H, ArH), 8.03-7.99 (m, 2H, ArH),
7.93-7.83 (m, 2H, ArH), 7.57-7.54 (m, 4H, ArH), 7.47-7.44
(m, 1H, ArH), 6.78 (s, 2H, ArH ), 4.34 (s, 3H, CH3), 3.69 (s,
6H, CH3); HRMS (ESI): m/z calcd for C44H29N3O3:
648.2282 [M+H]+, found: 648.2354.
19-(4-Bromophenyl)naphtho[2,3-f](benzo[c]phenazine)[2,
1-b]quinoline (7j)
m.p.: 280-282oC; IR (KBr, ꢀ, cm-1): 3053.2, 1519.3,
1485.4, 1343.8, 1316.1, 1089.5, 1011.8, 955.7, 891.7, 769.0,
1
742.7; H NMR (400MHz, CDCl3, 25oC): ꢁ = 9.49 (d, J =
7.6 Hz, 1H, ArH), 9.30 (d, J = 7.6 Hz, 1H, ArH), 8.34 (s, 1H,
ArH ), 8.23 (d, J = 8.4 Hz, 1H, ArH), 8.12 (s, 2H, ArH ),
8.00-7.97 (m, 2H, ArH), 7.94-7.88 (m, 1H, ArH), 7.87-7.84
(m, 3H, ArH), 7.82-7.77 (m, 1H, ArH), 7.75-7.71 (m, 1H,
ArH), 7.58-7.48 (m, 2H, ArH), 7.43 (d, J = 8.0 Hz, 1H,
ArH), 7.38-7.34 (m, 3H, ArH); HRMS (ESI): m/z calcd for
C37H20BrN3: 586.0913 [M+H]+, found: 586.0912.
Crystal data for 7g: C33H18N4O3, yellow, crystal
dimension 0.34 x 0.09 x 0.07 mm, Triclinic, space group P-
1, a = 10.2377(9) Å, b = 10.8522(12) Å, c = 11.8273(13) Å, ꢀ
= 98.8780(10)o, ꢁ = 110.247(2)o, ꢂ = 100.8140(10)o, V =
1176.2(2) Å3, Mr = 518.51, Z = 2, Dc = 1.464 Mg/m3, ꢃ =
0.71073 Å, μ(Mo Kꢀ) = 0.096 mm-1, F(000) = 536, R =
0.0878, wR2 = 0.1452, S = 1.053, largest diff. Peak and hole:
0.316 and -0.210 e/Å3.
19-(2,4-Dichlorophenyl)naphtho[2,3-f](benzo[c]phenazine)
[2,1-b]quinoline (7k)
ACKNOWLEDGEMENTS
m.p.: 221-222oC; IR (KBr, ꢀ, cm-1): 3054.6, 1516.4,
1470.8, 1352.3, 1090.6, 1018.2, 890.0, 768.1, 748.9; 1H
NMR (400MHz, DCCl3, 25oC): ꢁ = 9.51 (dd, J1 = 8.0 Hz, J2
= 1.2 Hz, 1H, ArH), 9.32 (d, J = 7.6 Hz, 1H, ArH), 8.38 (s,
1H, ArH ), 8.26 (d, J = 8.4 Hz, 1H, ArH), 8.16-8.13 (m, 2H,
ArH), 8.04-8.007.95-7.80 (m, 4H, ArH), 7.77-7.73 (m, 1H,
ArH), 7.60-7.48 (m, 4H, ArH), 7.40-7.38 (m, 1H, ArH), 7.30
(d, J = 8.0 Hz, 1H, ArH); HRMS (ESI): m/z calcd for
C37H19Cl2N3: 576.1029 [M+H]+, found: 576.1017.
We are grateful for financial support from the National
Science Foundation of China (21072163 and 21102124),
PAPD of Jiangsu Higher Education Institutions, Science
Foundation in Interdisciplinary Major Research Project of
Xuzhou Normal University (No. 09XKXK01), Doctoral
Research Foundation of Xuzhou Normal Univ. (XZNU, No.
10XLR20) and the NSF of Jiangsu Education Committee
(11KJB150016).
CONFLICT OF INTEREST
19-(3,4-Dimethoxyphenyl)naphtho[2,3-f](benzo[c]phena-
zine)[2,1-b]quinoline (7l)
Declared none.
m.p.: >300oC; IR (KBr, ꢀ, cm-1): 3053.6, 1510.9, 1463.5,
1346.7, 1313.1, 1248.1, 1142.3, 1025.8, 893.1, 766.8, 743.6;
1H NMR (400MHz, DCCl3, 25oC): ꢁ = 9.54 (d, J = 7.2 Hz,
1H, ArH), 9.32 (d, J = 7.2 Hz, 1H, ArH), 8.35 (s, 1H, ArH),
8.23 (d, J = 7.6 Hz, 1H, ArH), 8.15-8.11 (m, 2H, ArH), 7.99
(d, J = 8.4 Hz, 1H, ArH), 7.95-7.85 (m, 2H, ArH), 7.80-7.77
(m, 1H, ArH), 7.69-7.65 (m, 1H, ArH), 7.56-7.52 (m, 1H,
ArH), 7.45-7.44 (m, 2H, ArH), 7.41 (d, J = 7.6 Hz, 1H,
ArH), 7.20 (d, J = 8.0 Hz, 1H, ArH), 7.11 (d, J = 2.0 Hz, 1H,
ArH), 9.92 (dd, J1 = 8.0 Hz, J2 = 2.0 Hz, 1H, ArH), 4.19 (s,
3H, CH3), 3.74 (s, 3H, CH3); HRMS (ESI): m/z calcd for
C37H22ClN3: 568.2020 [M+H]+, found: 568.2020.
SUPPLEMENTARY MATERIAL
Supplementary material is available on the publisher’s
web site along with the published article.
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Received: July 3, 2011
Revised: November 8, 2011
Accepted: November 14, 2011