Palladium-catalyzed three-component reaction of 2-alkynylbromobenzene, 2-alkynylaniline, and electrophile: An efficient pathway for the synthesis of diverse 11H-indeno[1,2-c]quinolines

Article abstract of DOI:10.1039/c2ob06764a

Diverse 11H-indeno[1,2-c]quinolines are produced via a palladium-catalyzed three-component reaction of 2-alkynylbromobenzene, 2-alkynylaniline, and electrophile. This conversion tolerates a wide variety of functionality and substitution patterns on the 11

Full text of DOI:10.1039/c2ob06764a

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PAPER
Palladium-catalyzed three-component reaction of 2-alkynylbromobenzene,
2-alkynylaniline, and electrophile: an efficient pathway for the synthesis of
diverse 11H-indeno[1,2-c]quinolines†
Xiaolin Pan,a Yong Luoa and Jie Wu*a,b
Received 20th October 2011, Accepted 13th December 2011
DOI: 10.1039/c2ob06764a
Diverse 11H-indeno[1,2-c]quinolines are produced via a palladium-catalyzed three-component reaction of
2-alkynylbromobenzene, 2-alkynylaniline, and electrophile. This conversion tolerates a wide variety of
functionality and substitution patterns on the 11H-indeno[1,2-c]quinoline ring.
preparation of nano and mesostructures with enhanced electronic
1. Introduction
and photonic properties.7 Additionally, applications of indene
compounds in drug discovery programs8 and materials science9
Since the completion of the Human Genome Project in 2003,
small molecules are in great demand in biomedical research
communities for the elucidation of gene functions and the
associated control of gene products.1 Among the molecules,
natural products or natural product-like compounds have been
identified as therapeutic agents or functional modulators of
specific biological processes. Therefore, continuous efforts are
given towards the generation of natural product-like compounds
with privileged substructures via diversity-oriented synthesis.2
The widespread use of 2-alkynylhalobenzenes in organic
syntheses is attributable to their versatility in carbon–carbon
bond forming reactions, which have been successfully applied in
the synthesis of diverse heterocyclic systems.3,4 We have pre-
viously reported4 the discovery of a novel route for the prep-
aration of functionalized polycyclic structures starting from 2-
alkynylhalobenzenes via tandem reactions.5 During the reaction
process, molecular diversity and complexity could be introduced
easily in an efficient pathway. For instance, 11H-indeno[1,2-c]
quinolin-11-ols could be generated through a palladium-cata-
lyzed three-component reaction of 2-alkynylhalobenzene and 2-
alkynylaniline.4c A subsequent insertion of two triple bonds was
involved in this transformation. 11H-Indeno[1,2-c]quinoline,
which incorporates both quinoline and indene skeletons in one
molecule, could be recognized as a privileged scaffold as well. It
is well known that quinoline can be found in many natural pro-
ducts and pharmaceuticals with remarkable biological activities.6
Moreover, quinoline compounds are valuable synthons for the
have been demonstrated. As part of our efforts towards the gener-
ation of natural product-like compounds10 and with an expec-
tation for the application of the 11H-indeno[1,2-c]quinoline
library in different biological evaluations, efficient pathways for
the preparation of diverse 11H-indeno[1,2-c]quinolines are
needed. Herein, we wish to report our recent efforts for the con-
struction of functionalized 11H-indeno[1,2-c]quinolines via a
palladium-catalyzed three-component reaction of 2-alkynylbro-
mobenzenes, 2-alkynylanilines, and electrophiles (such as allylic
bromide, NBS, and NCS).
2. Results and discussion
We began our investigation by reacting 2-alkynylbromobenzene
1a, 2-alkynylaniline 2a, with allylic bromide 3 under palladium-
catalyzed reaction conditions (Table 1). As mentioned in our pre-
vious report,4c 6,11-diphenyl-5H-indeno[1,2-c]quinoline
A
would be the key intermediate during the reaction process. In the
presence of a base and allylic bromide, an intermolecular nucleo-
philic attack would occur to afford the corresponding product
4a. After screening the effects of ligands, bases, and solvents in
a combinatorial format, we rapidly noticed that the reaction
worked efficiently catalyzed by palladium acetate (5 mol%) and
tricyclohexylphosphine (10 mol%) in the presence of NaOtBu
as the base in 1,4-dioxane at 100 °C. The desired 11H-indeno
[1,2-c]quinoline 4a was isolated in 88% yield.
With the optimized reaction conditions in hand, the scope of
the palladium-catalyzed three-component reaction of 2-alkynyl-
bromobenzenes, 2-alkynylanilines, and allylic bromide was sub-
sequently studied (Table 2). In general, these reactions worked
well, giving rise to the corresponding 11H-indeno[1,2-c]quino-
lines 4 in moderate to good yields. 2-Alkynylanilines 2 bearing
either electron-rich or electron-poor substituents in the aromatic
aDepartment of Chemistry, Fudan University, 220 Handan Road,
Shanghai 200433, China. E-mail: jie_wu@fudan.edu.cn;
Fax: +86 21 6564 1740; Tel: +86 21 6510 2412
bJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science &
Technology Normal University, Nanchang 330013, China
†Electronic supplementary information (ESI) available. See DOI:
10.1039/c2ob06764a
This journal is © The Royal Society of Chemistry 2012
Org. Biomol. Chem., 2012, 10, 1969–1975 | 1969

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Table 1 Initial studies of the palladium-catalyzed reaction of 2-
alkynylbromobenzene 1a and 2-alkynylaniline 2a with allylic bromide 3
Table 2 Palladium-catalyzed three-component reaction of 2-
alkynylbromobenzene 1, 2-alkynylaniline 2, with allylic bromide 3a
Entry
1
Product
Entry
8
Product
Entry
Ligand
Base
Solvent
Yield (%)a
2
3
4
5
6
9
1
2
3
4
5
6
7
8
PCy3
PCy3
PCy3
PCy3
PCy3
PCy3
DPE Phos
Xant Phos
X-Phos
PPh3
K3PO4
Cs2CO3
KOH
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
DMF
nr
nr
nr
nr
trace
88
50
70
trace
nr
K2CO3
NaOMe
t-BuONa
t-BuONa
t-BuONa
t-BuONa
t-BuONa
t-BuONa
t-BuONa
10
11
12
13
9
10
11
12
PCy3
PCy3
nr
nr
toluene
a Isolated yield based on 2-alkynylaniline 2.
ring were converted to the desired products with good reactivity.
For instance, 2-alkynyl-4-methylaniline reacted with 2-alkynyl-
bromobenzene 1a and allylic bromide 3, leading to compound
4b in 83% yield (Table 2, entry 2). When 2-alkynyl-4-chloroani-
line was used as a replacement in the above reaction, the
expected 11H-indeno[1,2-c]quinolines 4c was produced in 72%
yield (Table 2, entry 3). For the reactions of 2-alkynylaniline 2
with other substituents at the R4 position, good yields were
observed (Table 2, entries 4–7). For example, reaction of 2-alky-
nylbromobenzene 1a, allylic bromide, and 2-alkynyl-4-methyl-
aniline with a 4-methylphenyl group at the R4 position afforded
the desired product 4f in 78% yield (Table 2, entry 6). However,
the reaction employing chloro-substituted 2-alkynylaniline in the
above conversion furnished product 4h in 50% yield (Table 2,
entry 8). A lower yield was obtained when methyl-substituted 2-
alkynylbromobenzene was utilized in the palladium-catalyzed
three-component reaction (Table 2, entry 9). We noticed that an
excellent result was generated for the reaction of 2-alkynylbro-
mobenzene with a 4-chlorophenyl group at the R2 position (93%
yield, Table 2, entry 12). The reactivity was diminished when
the R2 position was replaced by a 4-methyl- or 4-methoxyphenyl
group (Table 2, entries 10 and 11). A low yield (36%) was
obtained when 2-alkynylbromobenzene with a n-butyl group
attached on the R2 position was used (Table 2, entry 13).
7
a Isolated yield based on 2-alkynylaniline 2.
(Table 3, entry 1). Moderate yields were obtained when other
2-alkynylbromobenzenes were employed in the transformation
(Table 3, entries 2–4). NCS was a suitable reactant as well, and
the corresponding products 6 were prepared in moderate to good
yields (Table 3, entries 5–14). However, only a trace amount of
product was detected for the 2-alkynylbromobenzene or 2-alky-
nylaniline with an alkyl group attached at the R2 or R4 position
(Table 3, entries 15 and 16).
In conclusion, we have developed an efficient route for the
synthesis of diverse 11H-indeno[1,2-c]quinolines through a pal-
ladium-catalyzed three-component reaction of 2-alkynylbromo-
benzene, 2-alkynylaniline, and electrophile (such as allylic
bromide, NBS and NCS). This conversion tolerates a wide
variety of functionality and substitution patterns on the 11H-
In an effort to further expand the scope of this reaction, we
next explored the palladium-catalyzed three-component reaction
of 2-alkynylbromobenzene and 2-alkynylaniline with NBS
or NCS (Table 3). The reactions proceeded under the standard
conditions shown in Table 1. Reaction of 2-alkynylbromoben-
zene 1a, 2-alkynylaniline 2a, with NBS afforded the bromo-
substituted 11H-indeno[1,2-c]quinoline 5a in 82% yield
1970 | Org. Biomol. Chem., 2012, 10, 1969–1975
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Table 3 Palladium-catalyzed three-component reaction of 2-
alkynylbromobenzene 1 and 2-alkynylaniline 2 with NBS or NCSa
coated with 0.25 mm 230–400 mesh silica gel impregnated with
a fluorescent indicator (254 nm). Thin layer chromatography
plates were visualized by exposure to ultraviolet light. Organic
solutions were concentrated at ∼20 Torr (house vacuum) at
25–35 °C. Solvents were re-distilled prior to use in the reactions.
1
Other commercial reagents were used as received. H and 13C
NMR spectra were recorded in CDCl3 on a Bruker DRX-400
spectrometer operating at 400 MHz and 100 MHz, respectively.
All chemical shift values are quoted in ppm and coupling con-
stants quoted in Hz. High resolution mass spectrometry (HRMS)
spectra were obtained on a micrOTOF II Instrument. IR spectra
were run on a FTIR-360 spectrophotometer.
Entry
1
Product
Entry
9
Product
2
3
4
5
6
7
10
11
12
13
14
15
General experimental procedure for palladium-catalyzed
three-component reaction of 2-alkynylbromobenzene,
2-alkynylaniline, and electrophile
2-Alkynylbromobenzene (0.24 mmol) was added to a mixture of
Pd(OAc)2 (5 mol%), tricyclohexylphosphine (10 mol%),
t-BuONa (0.8 mmol), and 2-alkynylaniline (0.20 mmol) in 1,4-
dioxane (2.0 mL). The mixture was heated at 100 °C. After
2-alkynylaniline was consumed completely, an electrophile
(allylic bromide, NBS or NCS, 0.3 mmol) was added to the
mixture. After completion of the reaction as indicated by TLC,
the reaction was cooled and the solvent was diluted by EtOAc
(10 mL), washed with saturated brine (2 × 10 mL), and dried by
anhydrous Na2SO4. Evaporation of the solvent followed by
purification on silica gel provides the product (11H-indeno
[1,2-c]quinolines 4–6).
11-Allyl-6,11-diphenyl-11H-indeno[1,2-c]quinoline
(4a). IR
3058.3, 2922.9, 2845.6, 1637.9, 1599.9, 1496.0, 1456.7,
1442.5 cm−1. 1H NMR (400 MHz, CDCl3) δ 8.24–8.22 (m, 1H),
7.77–7.76 (m, 2H), 7.63–7.56 (m, 5H), 7.37–7.33 (m, 1H),
7.26–7.16 (m, 7H), 7.08–7.04 (m, 1H), 7.00–6.98 (m, 1H),
4.84–4.75 (m, 1H), 4.56–4.47 (m, 2H), 3.58 (d, J = 7.2 Hz, 2H).
13C NMR (100 MHz, CDCl3) δ 155.8, 155.7, 152.9, 147.2,
142.7, 140.5, 138.4, 132.7, 131.6, 130.4, 128.8, 128.7, 128.6,
127.6, 127.0, 126.9, 126.5, 126.3, 124.0, 123.9, 123.6, 122.8,
117.9, 59.4, 41.3. HRMS (ESI) calcd for C31H23N: 410.1909
(M + H+), found: 410.1880.
8
16
11-Allyl-2-methyl-6,11-diphenyl-11H-indeno[1,2-c]quinoline
(4b). IR 3058.7, 2922.9, 2854.0, 1634.6, 1594.9, 1561.3,
1495.0, 1467.1, 1443.0, 1364.9 cm−1 1H NMR (400 MHz,
.
a Isolated yield based on 2-alkynylaniline 2.
CDCl3) δ 8.12 (d, J = 8.8 Hz, 1H), 7.76–7.74 (m, 2H),
7.59–7.54 (m, 3H), 7.44 (d, J = 8.8 Hz, 1H), 7.36 (s, 1H),
7.26–7.15 (m, 7H), 7.05 (t, J = 7.6 Hz, 1H), 6.99–6.97 (m, 1H),
4.84–4.75 (m, 1H), 4.58–4.48 (m, 2H), 3.58 (dd, J = 6.8, 3.2
Hz, 2H), 2.37 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 154.9,
153.0, 147.3, 145.8, 142.8, 140.7, 138.6, 136.2, 132.6, 131.8,
131.1, 130.1, 128.9, 128.8, 128.7, 128.6, 127.5, 126.9, 126.8,
126.3, 124.0, 123.6, 122.8, 117.8, 59.3, 41.1, 22.0. HRMS (ESI)
calcd for C32H25N: 424.2065 (M + H+), found: 424.2066.
indeno[1,2-c]quinoline ring. Exploration of other transformations
of 2-alkynylhalobenzenes is in progress in our laboratory.
Experimental section
11-Allyl-2-chloro-6,11-diphenyl-11H-indeno[1,2-c]quinoline
All reactions were performed in test tubes under nitrogen atmos-
phere. Flash column chromatography was performed using silica
gel (60 Å pore size, 32–63 μm, standard grade). Analytical thin–
layer chromatography was performed using glass plates pre-
(4c). IR 3060.6, 2925.5, 2853.5, 1640.7, 1601.3, 1563.4,
1
1491.8, 1462.3, 1444.3 cm−1. H NMR (400 MHz, CDCl3)
δ
8.15 (d, J = 8.8 Hz, 1H), 7.76–7.74 (m, 2H), 7.61–7.53 (m, 5H),
7.29–7.17 (m, 7H), 7.10–7.06 (m, 1H), 7.02–7.00 (m, 1H),
This journal is © The Royal Society of Chemistry 2012
Org. Biomol. Chem., 2012, 10, 1969–1975 | 1971

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4.85–4.74 (m, 1H), 4.60–4.50 (m, 2H), 3.58–3.54 (m, 2H). 13C
NMR (100 MHz, CDCl3) δ 156.0, 154.9, 153.1, 145.5, 142.0,
140.2, 138.1, 133.5, 132.2, 132.1, 131.4, 129.0, 128.9, 128.8,
128.8, 128.7, 128.0, 127.3, 127.0, 126.3, 124.6, 123.7, 123.0,
122.6, 118.2, 59.4, 41.1. HRMS (ESI) calcd for C31H22ClN:
444.1519 (M + H+), found: 444.1503.
11-Allyl-2-chloro-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]qui-
noline (4h). IR 3051.6, 2925.3, 2855.1, 1643.7, 1608.8, 1563.1,
1491.5, 1462.3, 1444.6, 1362.8 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.14 (d, J = 8.8 Hz, 1H), 7.76–7.74 (m, 2H),
7.61–7.53 (m, 5H), 7.21–7.20 (m, 2H), 7.09–7.05 (m, 5H),
7.01–6.99 (m, 1H), 4.82–4.74 (m, 1H), 4.59–4.49 (m, 2H),
3.55–3.53 (m, 2H), 2.29 (s, 3H). 13C NMR (100 MHz, CDCl3) δ
156.0, 155.0, 153.3, 145.5, 140.3, 138.9, 138.0, 136.9, 133.5,
132.1, 132.0, 131.5, 129.7, 129.0, 128.8, 128.7, 128.0, 126.9,
126.1, 124.7, 123.6, 123.0, 122.7, 118.1, 59.2, 41.2, 21.0.
HRMS (ESI) calcd for C32H24ClN: 458.1676 (M + H+), found:
458.1670.
11-Allyl-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]quinoline
(4d). IR 3059.2, 2921.7, 2847.8, 1634.6, 1561.4, 1509.6,
1491.3, 1466.9, 1436.4, 1366.3 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.22 (d, J = 8.4 Hz, 1H), 7.77–7.75 (m, 2H),
7.65–7.63 (m, 1H), 7.61–7.55 (m, 3H), 7.35 (t, J = 8.0 Hz, 1H),
7.22–7.15 (m, 2H), 7.09–7.06 (m, 6H), 7.00–6.98 (m, 1H),
4.83–4.77 (m, 1H), 4.56–4.46 (m, 2H), 3.56 (d, J = 6.8 Hz, 2H),
2.27 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 155.8, 155.07,
153.1, 147.2, 140.6, 139.6, 138.4, 136.5, 132.6, 131.8, 130.4,
129.5, 128.8, 128.8, 128.7, 128.6, 127.6, 126.8, 126.4, 126.2,
124.0, 123.9, 123.5, 122.8, 117.8, 59.1, 41.3, 20.9. HRMS (ESI)
calcd for C32H25N: 424.2065 (M + H+), found: 424.2070.
11-Allyl-8-methyl-6,11-diphenyl-11H-indeno[1,2-c]quinoline
(4i). IR 3058.2, 2921.8, 2853.8, 1634.6, 1607.1, 1567.6,
1498.3, 1463.3, 1443.8, 1372.8 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.23–8.21 (m, 1H), 7.77–7.75 (m, 2H), 7.62–7.58 (m,
5H), 7.37–7.33 (m, 1H), 7.26–7.18 (m, 5H), 7.10 (d, J = 7.6 Hz,
1H), 7.00 (d, J = 8.0 Hz, 1H), 6.77 (s, 1H), 4.85–4.79 (m, 1H),
4.57–4.47 (m, 2H), 3.56 (d, J = 6.8 Hz, 2H), 2.17 (s, 3H). 13C
NMR (100 MHz, CDCl3) δ 156.0, 155.8, 150.2, 147.2, 143.0,
140.6, 138.6, 136.5, 132.8, 131.9, 130.5, 128.9, 128.8, 128.8,
128.7, 128.6, 128.5, 126.9, 126.4, 126.3, 125.2, 124.0, 123.6,
123.3, 117.8, 59.1, 41.3, 21.6. HRMS (ESI) calcd for C32H25N:
424.2065 (M + H+), found: 424.2057.
11-Allyl-11-(4-chlorophenyl)-6-phenyl-11H-indeno[1,2-c]qui-
noline (4e). IR 3061.1, 2923.6, 2852.1, 1640.2, 1565.4, 1491.6,
1
1463.7, 1444.0 cm−1. H NMR (400 MHz, CDCl3) δ 8.24 (d, J
= 8.8 Hz, 1H), 7.76–7.75 (m, 2H), 7.65–7.57 (m, 5H),
7.40–7.36 (m, 1H), 7.23–7.18 (m, 4H), 7.13–7.11 (m, 2H),
7.09–7.05 (m, 1H), 7.00 (d, J = 7.6 Hz, 1H), 4.82–4.74 (m, 1H),
4.56–4.48 (m, 2H), 3.54 (d, J = 7.2 Hz, 2H). 13C NMR
(100 MHz, CDCl3) δ 155.8, 155.1, 152.4, 147.2, 141.4, 140.4,
138.4, 132.8, 132.7, 131.3, 130.6, 129.0, 128.9, 128.9, 128.8,
128.7, 127.8, 127.7, 127.1, 126.6, 123.7, 123.5, 122.9, 118.2,
58.9, 41.2. HRMS (ESI) calcd for C31H22ClN: 444.1519
(M + H+), found: 444.1508.
11-Allyl-11-phenyl-6-(p-tolyl)-11H-indeno[1,2-c]quinoline
(4j). IR 3060.4, 2922.5, 2853.2, 1640.4, 1608.8, 1582.5,
1500.1, 1464.1, 1445.1, 1414.0 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.22–8.20 (m, 1H), 7.66 (d, J = 7.6 Hz, 2H),
7.61–7.59 (m, 2H), 7.39 (d, J = 8.0 Hz, 2H), 7.34 (t, J = 7.6 Hz,
1H), 7.26–7.18 (m, 7H), 7.09 (s, 2H), 4.83–4.77 (m, 1H),
4.56–4.46 (m, 2H), 3.58 (d, J = 7.2 Hz, 2H), 2.50 (s, 3H). 13C
NMR (100 MHz, CDCl3) δ 155.9, 155.6, 152.9, 147.3, 142.8,
138.6, 137.7, 132.7, 131.7, 130.4, 129.3, 128.8, 128.7, 127.5,
127.0, 126.8, 126.4, 126.3, 124.0, 123.9, 123.6, 122.9, 117.9,
59.4, 41.3, 21.5. HRMS (ESI) calcd for C32H25N: 424.2065
(M + H+), found: 424.2062.
11-Allyl-2-methyl-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]qui-
noline (4f). IR 3057.4, 2921.0, 2855.6, 1640.6, 1622.4, 1561.4,
1
1497.7.7, 1467.0, 1442.8, 1366.3 cm−1. H NMR (400 MHz,
CDCl3) δ 8.11 (d, J = 8.4 Hz, 1H), 7.75 (d, J = 6.8 Hz, 2H),
7.58–7.56 (m, 3H), 7.46–7.40 (m, 2H), 7.20–7.14 (m, 2H),
7.09–7.03 (m, 5H), 6.98–6.96 (m, 1H), 4.83–4.75 (m, 1H),
4.57–4.47 (m, 2H), 3.58–3.55 (m, 2H), 2.38 (s, 3H), 2.27 (s,
3H). 13C NMR (100 MHz, CDCl3) δ 155.0, 154.8, 153.1, 145.8,
140.7, 139.7, 138.6, 136.4, 136.2, 132.6, 131.9, 131.1, 130.1,
129.4, 128.9, 128.7, 128.6, 127.5, 126.7, 126.1, 124.0, 123.5,
122.8, 122.7, 117.7, 59.1, 41.1, 22.0, 21.0. HRMS (ESI) calcd
for C33H27N: 438.2222 (M + H+), found: 438.2208.
11-Allyl-6-(4-methoxyphenyl)-11-phenyl-11H-indeno[1,2-c]
quinoline (4k). IR 3053.7, 2928.3, 2853.7, 1641.5, 1608.9,
1573.1, 1501.7, 1465.1, 1444.3, 1377.8, 1265.1, 1032.4 cm−1
.
1H NMR (400 MHz, CDCl3) δ 8.21 (d, J = 8.8 Hz, 1H), 7.72 (d,
J = 8.8 Hz, 2H), 7.60 (d, J = 7.6 Hz, 2H), 7.36–7.32 (m, 1H),
7.26–7.19 (m, 7H), 7.13–7.09 (m, 4H), 4.83–4.75 (m, 1H),
4.57–4.47 (m, 2H), 3.94 (s, 3H), 3.58 (d, J = 6.8 Hz, 2H). 13C
NMR (100 MHz, CDCl3) δ 160.1, 155.7, 155.6, 152.9, 147.3,
142.8, 138.7, 133.1, 132.8, 131.7, 130.4, 130.3, 128.8, 128.7,
127.6, 127.0, 126.9, 126.4, 126.3, 124.0, 123.8, 123.6, 122.9,
117.9, 114.0, 59.4, 41.3, 29.7. HRMS (ESI) calcd for
C32H25NO: 440.2014 (M + H+), found: 440.2000.
11-Allyl-11-(4-chlorophenyl)-2-methyl-6-phenyl-11H-indeno
[1,2-c]quinoline (4g). IR 3060.3, 2921.7, 2854.4, 1643.7,
1
1622.4, 1561.4, 1492.0, 1467.6, 1442.2, 1364.8 cm−1. H NMR
(400 MHz, CDCl3) δ 8.12 (d, J = 8.8 Hz, 1H), 7.74 (d, J = 6.4
Hz, 2H), 7.59–7.54 (m, 3H), 7.48–7.45 (m, 1H), 7.32 (s, 1H),
7.24–7.21 (m, 2H), 7.18–7.11 (m, 4H), 7.08–7.04 (m, 1H),
6.99–6.97 (m, 1H), 4.82–4.74 (m, 1H), 4.58–4.48 (m, 2H),
3.56–3.52 (m, 2H), 2.40 (s, 3H). 13C NMR (100 MHz, CDCl3) δ
154.9, 154.2, 152.4, 145.9, 141.5, 140.5, 138.5, 136.5, 132.7,
132.6, 131.4, 131.3, 130.3, 128.9, 128.8, 128.7, 128.6, 127.7,
127.6, 127.0, 123.8, 123.4, 122.9, 122.5, 118.1, 58.8, 41.1, 22.0.
HRMS (ESI) calcd for C32H24ClN: 458.1676 (M + H+), found:
458.1678.
11-Allyl-6-(4-chlorophenyl)-11-phenyl-11H-indeno[1,2-c]qui-
noline (4l). IR 3060.8, 2924.4, 2853.6, 1646.7, 1596.6, 1565.3,
1
1491.4, 1464.8, 1445.0 cm−1. H NMR (400 MHz, CDCl3)
δ
8.21–8.19 (m, 1H), 7.73 (d, J = 8.4 Hz, 2H), 7.63–7.56 (m, 4H),
7.37–7.34 (m, 1H), 7.26–7.18 (m, 7H), 7.13–7.06 (m, 2H),
4.84–4.74 (m, 1H), 4.55–4.46 (m, 2H), 3.58 (d, J = 7.2 Hz, 2H).
13C NMR (100 MHz, CDCl3) δ 156.0, 154.4, 152.9, 147.2,
142.6, 139.0, 138.2, 134.9, 132.5, 131.6, 130.4, 129.0, 128.9,
1972 | Org. Biomol. Chem., 2012, 10, 1969–1975
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128.8, 127.8, 127.0, 126.9, 126.7, 126.3, 124.0, 123.7, 122.6,
118.0, 59.4, 41.3. HRMS (ESI) calcd for C31H22ClN: 444.1519
(M + H+), found: 444.1516.
125.2, 125.1, 124.1, 122.8, 67.0, 21.6. HRMS (ESI) calcd for
C29H20BrN: 462.0857 (M + H+), found: 462.0849.
11-Chloro-6,11-diphenyl-11H-indeno[1,2-c]quinoline (6a). IR
3059.7, 2927.0, 2852.6, 1599.4, 1584.3, 1493.3, 1445.4 cm−1
.
11-Allyl-6-butyl-11-phenyl-11H-indeno[1,2-c]quinoline
(4m). IR 3055.7, 2926.1, 2857.6, 1646.7, 1598.6, 1573.6,
1H NMR (400 MHz, CDCl3) δ 8.26 (d, J = 8.4 Hz, 1H),
7.79–7.77 (m, 3H), 7.68–7.65 (m, 1H), 7.60–7.59 (m, 3H),
7.49–7.40 (m, 4H), 7.30–7.28 (m, 3H), 7.24–7.19 (m, 1H), 7.10
(t, J = 7.6 Hz, 1H), 7.00–6.98 (d, J = 7.6 Hz, 1H). 13C NMR
(100 MHz, CDCl3) δ 155.7, 152.9, 150.8, 147.9, 139.7, 139.2,
136.3, 130.6, 130.2, 129.6, 129.2, 128.8, 128.7, 128.6, 128.5,
128.3, 127.1, 126.0, 125.0, 124.7, 123.3, 122.7, 67.0. HRMS
(ESI) calcd for C28H18ClN: 404.1206 (M + H+), found:
404.1182.
1494.3, 1466.9, 1442.5, 1405.9 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.13 (d, J = 8.2 Hz, 1H), 7.92 (d, J = 7.8 Hz, 1H),
7.62–7.54 (m, 2H), 7. 44–7.38 (m, 1H), 7.29–7.21 (m, 6H),
7.14–7.12 (m, 2H), 4.69–4.65 (m, 1H), 4.51–4.47 (m, 1H),
4.41–4.39 (m, 1H), 3.55–3.45 (m, 2H), 1.96–1.94 (m, 2H),
1.69–1.61 (m, 3H), 1.26 (s, 1H), 1.07–1.04 (m, 3H).13C NMR
(100 MHz, CDCl3) δ 158.2, 155.1, 153.2, 147.2, 142.8, 138.8,
128.8, 128.5, 127.5, 127.4, 126.3, 124.0, 123.8, 122.7, 117.8,
59.3, 41.2, 37.9, 30.6, 23.1. HRMS (ESI) calcd for C29H27N:
390.2222 (M + H+), found: 390.2200.
2,11-Dichloro-6,11-diphenyl-11H-indeno[1,2-c]quinoline
(6b). IR 3056.5, 2925.3, 2855.3, 1607.1, 1573.6, 1491.3,
11-Bromo-6,11-diphenyl-11H-indeno[1,2-c]quinoline (5a). IR
1
1462.5 cm−1. H NMR (400 MHz, CDCl3) δ 8.16 (d, J = 9.2
3058.8, 2926.0, 2854.5, 1596.5, 1583.2, 1499.3, 1444.7 cm−1
.
Hz, 1H), 7.77–7.73 (m, 3H), 7.61–7.58 (m, 4H), 7.47–7.41 (m,
3H), 7.34–7.31 (m, 3H), 7.26–7.22 (m, 1H), 7.12 (t, J = 8.0 Hz,
1H NMR (400 MHz, CDCl3) δ 8.26 (d, J = 8.4 Hz, 1H),
7.78–7.75 (m, 3H), 7.68–7.64 (m, 1H), 7.61–7.57 (m, 3H),
7.52–7.42 (m, 4H), 7.28–7.27 (m, 3H), 7.24–7.19 (m, 1H),
7.10–7.06 (m, 1H), 6.99–6.97 (m, 1H). 13C NMR (100 MHz,
CDCl3) δ 156.0, 153.0, 151.3, 148.1, 140.0, 139.1, 135.7, 130.3,
129.6, 129.1, 128.9, 128.8, 128.7, 128.6, 128.5, 128.4, 128.3,
127.1, 126.7, 125.5, 125.1, 122.8, 123.4, 65.5. HRMS (ESI)
calcd for C28H18BrN: 448.0701 (M + H+), found: 448.0696.
1H), 7.01 (d, J = 7.6 Hz, 1H). 13C NMR (100 MHz, CDCl3)
δ
156.0, 151.2, 150.9, 146.4, 139.6, 138.6, 136.0, 132.9, 131.9,
131.4, 130.5, 129.3, 129.0, 128.9, 128.8, 128.7, 128.5, 125.9,
125.0, 123.5, 123.4, 67.0. HRMS (ESI) calcd for C28H17Cl2N:
438.0816 (M + H+), found: 438.0820.
11-Chloro-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]quinoline
(6c). IR 3058.1, 2926.4, 2853.3, 1608.2, 1570.8, 1509.1,
11-Bromo-6-(4-methoxyphenyl)-11-phenyl-11H-indeno[1,2-c]
quinoline (5b). IR 3054.4, 2986.1, 2932.0, 1609.0, 1563.1,
1
1467.8, 1446.0, 1360.2 cm−1. H NMR (400 MHz, CDCl3)
δ
8.20 (d, J = 8.4 Hz, 1H), 7.81–7.75 (m, 3H), 7.68–7.65 (m, 1H),
7.60–7.58 (m, 3H), 7.43–7.41 (m, 2H), 7.36–7.34 (m, 2H),
7.24–7.19 (m, 1H), 7.10–7.09 (m, 3H), 7.98–7.97 (m, 1H), 2.30
(s, 3H). 13C NMR (100 MHz, CDCl3) δ 155.8, 152.7, 151.0,
148.1, 140.1, 138.1, 136.3, 136.2, 130.3, 129.5, 129.4, 129.1,
128.9, 128.8, 128.7, 128.6, 127.0, 125.90, 124.9, 124.8, 123.3,
122.8, 73.5, 21.0. HRMS (ESI) calcd for C29H20ClN: 418.1363
(M + H+), found: 418.1384.
1501.9, 1465.4, 1442.4, 1265.2, 1034.0 cm−1
.
1H NMR
(400 MHz, CDCl3) δ 8.25 (d, J = 8.4 Hz, 1H), 7.77–7.71 (m,
3H), 7.67–7.63 (m, 1H), 7.51–7.49 (m, 3H), 7.44–7.41 (m, 1H),
7.28–7.27 (m, 3H), 7.25–7.20 (m, 1H), 7.13–7.11 (m, 4H), 3.93
(s, 3H). 13C NMR (100 MHz, CDCl3) δ 160.3, 155.7, 153.1,
151.3, 148.1, 139.1, 135.9, 132.4, 130. 3, 130.2, 129.8, 129.5,
128.7, 128.6, 128.5, 128.3, 127.1, 126.6, 125.5, 123.4, 122.6,
114.1, 65.6, 55.4. HRMS (ESI) calcd for C29H20BrNO:
478.0807 (M + H+), found: 478.0784.
11-Chloro-11-(4-chlorophenyl)-6-phenyl-11H-indeno[1,2-c]
quinoline (6d). IR 3058.1, 2924.4, 2847.8, 1582.7, 1579.7,
11-Bromo-8-chloro-6,11-diphenyl-11H-indeno[1,2-c]quinoline
(5c). IR 3059.6, 2924.7, 2851.9, 1597.2, 1576.5, 1492.1,
1
1491.3, 1451.7 cm−1. H NMR (400 MHz, CDCl3) δ 8.24 (d, J
1
1460.4 cm−1. H NMR (400 MHz, CDCl3) δ 8.27 (d, J = 8.8
= 9.2 Hz, 1H), 7.77–7.67 (m, 4H), 7.61–7.59 (m, 3H),
7.48–7.38 (m, 4H), 7.29–7.21 (m, 3H), 7.15–7.11 (m, 1H), 7.00
(d, J = 8.0 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 155.8,
152.1, 150.4, 148.1, 139.9, 138.0, 136.4, 134.3, 130.5, 129.7,
129.2, 129.0, 128.9, 128.8, 128.7, 127.5, 127.2, 124.9, 124.5,
123.4, 122.5, 72.9. HRMS (ESI) calcd for C28H17Cl2N:
438.0816 (M + H+), found: 438.0817.
Hz, 1H), 7.77–7.75 (m, 3H), 7.72–7.67 (m, 1H), 7.63–7.61 (m,
3H), 7.49–7.44 (m, 1H), 7.38 (d, J = 8.4 Hz, 3H), 7.30–7.28 (m,
3H), 7.18 (dd, J = 8.4, 2.0 Hz, 1H), 6.94 (m, 1H). 13C NMR
(100 MHz, CDCl3) δ 155.9, 153.7, 149.5, 148.4, 139.5, 138.5,
137.5, 134.6, 130.4 130.0, 129.4, 128.9, 128.8, 128.7, 128.6,
128.5, 127.0, 126.9, 126.5, 125.1, 123.6, 122.6, 67.0. HRMS
(ESI) calcd for C28H17BrClN: 482.0311 (M + H+), found:
482.0305.
11-Chloro-6-(4-methoxyphenyl)-11-phenyl-11H-indeno[1,2-c]
quinoline (6e). IR 3061.4, 2927.4, 2852.7, 1608.0, 1572.2,
11-Bromo-8-methyl-6,11-diphenyl-11H-indeno[1,2-c]quinoline
1501.3, 1445.1, 1366.0, 1249.3, 1030.9 cm−1 1H NMR
.
(5d). IR 3058.5, 2924.1, 2852.2, 1610.2, 1567.5, 1492.8,
(400 MHz, CDCl3) δ 8.22 (d, J = 8.4 Hz, 1H), 7.77–7.71 (m,
3H), 7.67–7.63 (m, 1H), 7.49–7.46 (m, 2H), 7.42–7.38 (m, 2H),
7.30–7.28 (m, 3H), 7.25–7.20 (m, 1H), 7.14–7.11 (m, 4H), 3.94
(s, 3H). 13C NMR (100 MHz, CDCl3) δ 160.3, 155.6, 152.6,
150.8, 148.2, 139.3, 136.6, 132.5, 130.7, 130.3, 129.5, 128.8,
128.7, 128.5, 128.2, 126.9, 126.0, 125.0, 124.7, 123.4, 122.5,
114.1, 73.5, 55.4. HRMS (ESI) calcd for C29H20ClNO:
434.1312 (M + H+), found: 434.1340.
1
1469.9, 1444.2, 1369.7 cm−1. H NMR (400 MHz, CDCl3)
δ
8.25 (d, J = 8.4 Hz, 1H), 7.78–7.75 (m, 3H), 7.68–7.64 (m, 1H),
7.61–7.58 (m, 3H), 7.51–7.49 (m, 2H), 7.46–7.42 (m, 1H), 7.36
(d, J = 8.0 Hz, 1H) 7.28–7.26 (m, 3H), 7.03 (d, J = 7.6 Hz, 1H),
6.77 (s, 1H), 2.16 (s, 3H). 13C NMR (100 MHz, CDCl3)
δ
156.0, 153.4, 148.6, 148.1, 140.1, 139.3, 138.6, 135.9, 130.3,
129.7, 129.5, 129.4, 129.1, 128.8, 128.7, 128.2, 127.0, 126.7,
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Org. Biomol. Chem., 2012, 10, 1969–1975 | 1973

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11-Chloro-8-methyl-6,11-diphenyl-11H-indeno[1,2-c]quinoline
Acknowledgements
(6f). IR 3058.3, 2925.5, 2853.2, 1604.1, 1573.6, 1488.2,
1
1466.9, 1445.2, 1369.4 cm−1. H NMR (400 MHz, CDCl3)
δ
Financial support from the National Natural Science Foundation
of China (Nos. 21032007, 21172038) and Jiangxi Key Labora-
tory of Organic Chemistry, Jiangxi Science & Technology
Normal University is gratefully acknowledged.
8.23 (d, J = 8.4 Hz, 1H), 7.77–7.76 (m, 3H), 7.69–7.64 (m, 1H),
7.61–7.59 (m, 3H), 7.48–7.42 (m, 3H), 7.30–7.25 (m, 4H), 7.04
(d, J = 7.6 Hz, 1H), 2.17 (s, 3H). 13C NMR (100 MHz, CDCl3)
δ 155.8, 153.1, 148.1, 148.0, 140.0, 139.5, 138.8, 136.6, 130.7,
130.3, 129.5, 129.4, 129.1, 128.9, 128.7, 128.6, 128.2, 127.0,
126.0, 124.7, 124.6, 124.1, 122.7, 73.5, 21.6. HRMS (ESI)
calcd for C29H20ClN: 418.1363 (M + H+), found: 418.1367.
Notes and references
1 (a) A. L. Hopkins and C. R. Groom, Nat. Rev. Drug Discovery, 2002, 1,
727; (b) R. L. Strausberg and S. L. Schreiber, Science, 2003, 300, 294;
(c) S. L. Schreiber, Nat. Chem. Biol., 2005, 1, 64; (d) B. S. Sekhon, Curr.
Chem. Biol., 2008, 2, 278; (e) D. P. Walsh and Y.-T. Chang, Chem. Rev.,
2006, 106, 2476; (f) P. Arya, D. T. H. Chou and M.-G. Baek, Angew.
Chem., Int. Ed., 2001, 40, 339.
11-Chloro-11-phenyl-6-(p-tolyl)-11H-indeno[1,2-c]quinoline
(6g). IR 3059.4, 2923.3, 2854.1, 1610.2, 1570.6, 1500.9,
1
1467.9, 1445.7, 1366.0 cm−1. H NMR (400 MHz, CDCl3) δ
2 S. L. Schreiber, Science, 2000, 287, 1964.
8.22 (d, J = 8.4 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.67–7.63
(m, 3H), 7.49–7.46 (m, 2H), 7.42–7.39 (m, 4H), 7.31–7.28 (m,
3H), 7.24–7.19 (m, 1H), 7.14–7.07 (m, 2H), 2.51 (s, 3H). 13C
NMR (100 MHz, CDCl3) δ 156.0, 152.6, 150.8, 148.2, 139.3,
139.0, 137.1, 136.6, 130.6, 130.3, 129.5, 129.4, 128.8, 128.7,
128.5, 128.2, 126.9, 126.0, 125.0, 124.7, 123.4, 122.6, 73.5,
21.5. HRMS (ESI) calcd for C29H20ClN: 418.1363 (M + H+),
found: 418.1365.
3 For selected examples, see: (a) Z.-Y. Tang and Q.-S. Hu, Adv. Synth.
Catal., 2006, 348, 846; (b) J. Takaya, S. Udagawa, H. Kusama and
N. Iwasawa, Angew. Chem., Int. Ed., 2008, 47, 4906; (c) H. Cao,
L. McNamee and H. Alper, Org. Lett., 2008, 10, 5281;
(d) L. Ackermann, S. Barfüßer and H. K. Potukuchi, Adv. Synth. Catal.,
2009, 351, 1064; (e) N. Halland, M. Nazaré, O. Rkyek, J. Alonso,
M. Urmann and A. Lindenschmidt, Angew. Chem., Int. Ed., 2009, 48,
6879; (f) H. Siebeneicher, I. Bytschkov and S. Doye, Angew. Chem., Int.
Ed., 2003, 42, 3042; (g) L. Ackermann, Org. Lett., 2005, 7, 439;
(h) R. Sanz, M. P. Castroviejo, V. Guilarte, A. Pérez and F. J. Fañanás,
J. Org. Chem., 2007, 72, 5113; (i) P.-Y. Yao, Y. Zhang, R. P. Hsung and
K. Zhao, Org. Lett., 2008, 10, 4275; ( j) L. Ackermann, R. Sandmann
and M. V. Kondrashov, Synlett, 2009, 1219; (k) L. T. Kaspar and
L. Ackermann, Tetrahedron, 2005, 61, 11311; (l) L. Ackermann,
R. Sandmann, M. Schinkel and M. V. Kondrashov, Tetrahedron, 2009,
65, 8930; (m) A. K. Verma, T. Kesharwani, J. Singh, V. Tandon and R.
C. Larock, Angew. Chem., Int. Ed., 2009, 48, 1138; (n) A. K. Verma,
M. Joshi and V. P. Singh, Org. Lett., 2011, 13, 1630.
11-Chloro-2-methyl-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]
quinoline (6h). IR 3056.4, 2924.5, 2854.6, 1628.5, 1570.5,
1494.3, 1466.9, 1442.5, 1366.3 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.12 (d, J = 8.8 Hz, 1H), 7.76–7.74 (m, 2H),
7.58–7.55 (m, 4H), 7.49 (d, J = 8.8 Hz, 1H), 7.41 (d, J = 7.6
Hz, 1H), 7.35 (d, J = 8.0 Hz, 2H), 7.19 (t, J = 7.6 Hz, 1H),
7.10–7.06 (m, 3H), 6.96 (d, J = 7.6 Hz, 1H), 2.40 (s, 3H), 2.30
(s, 3H). 13C NMR (100 MHz, CDCl3) δ 154.8, 151.8, 151.0,
146.8, 140.2, 138.0, 137.0, 136.4, 136.3, 131.9, 130.4, 130.0,
129.4, 128.9, 128.8, 128.7, 128.6, 128.4, 125.9, 124.9, 123.5,
123.2, 122.8, 73.6, 22.1, 21.0. HRMS (ESI) calcd for
C30H22ClN: 432.1519 (M + H+), found: 432.1508.
4 (a) Y. Luo, L. Hong and J. Wu, Chem. Commun., 2011, 47, 5298;
(b) Y. Luo, X. Pan and J. Wu, Org. Lett., 2011, 13, 1150; (c) X. Pan,
Y. Luo and J. Wu, Chem. Commun., 2011, 47, 8967; (d) Y. Luo and
J. Wu, Chem. Commun., 2011, 47, 11137; (e) X. Pan, Y. Luo, G. Liu,
S. Pu and J. Wu, Adv. Synth. Catal., 2012, 354, 171.
5 For selected reviews, see: (a) L. F. Tietze, G. Brasche and K. Gericke,
Domino Reactions in Organic SynthesisWiley-VCH, Weinheim,
Germany, 2006; (b) A. Meijere, P. V. Zezschwitz and S. Bräse, Acc.
Chem. Res., 2005, 38, 413; (c) P. Lu and Y.-G. Wang, Synlett, 2010, 165;
(d) E. J. Yoo and S. Chang, Curr. Org. Chem., 2009, 13, 1766;
(e) Multicomponent Reactions (ed.: J. Zhu and H. Bienaymé), Wiley-
VCH, Weinheim, 2005; (f) K. C. Nicolaou, E. W. Yue and T. Oshima, in
The New Chemistry (ed.: N. Hall), Cambridge University Press, Cam-
bridge, 2001, p. 168; (g) L. F. Tietze and F. Hautner, in Stimulating Con-
cepts in Chemistry (ed.: F. Vögtle, J. F. Stoddart and M. Shibasaki),
Wiley-VCH, Weinheim, 2000, p. 38; (h) A. Dömling and I. Ugi, Angew.
Chem., Int. Ed., 2000, 39, 3168; (i) L. F. Tietze, Chem. Rev., 1996, 96,
115; ( j) L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993,
32, 131.
6 For selected examples, see: (a) R. D. Larsen, E. G. Corley, A. O. King, J.
D. Carrol, P. Davis, T. R. Verhoeven, P. J. Reider, M. Labelle,
J. Y. Gauthier, Y. B. Xiang and R. Zamboni, J. Org. Chem., 1996, 61,
3398; (b) Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu and C. C. Tzeng,
J. Med. Chem., 2001, 44, 2374; (c) G. Roma, M. D. Braccio, G. Grossi
and M. Chia, Eur. J. Med. Chem., 2000, 35, 1021; (d) D. Doube,
M. Bloun, C. Brideau, C. Chan, S. Desmarais, D. Eithier,
J. P. Falgueyeret, R. W. Friesen, M. Girad, Y. Girad, J. Guay, P. Tagari
and R. N. Yong, Bioorg. Med. Chem. Lett., 1998, 8, 1255;
(e) M. P. Maguire, K. R. Sheets, K. Mcvety, A. P. Spada and
A. Zilberstein, J. Med. Chem., 1994, 37, 2129; (f) O. Bilker, V. Lindo,
M. Panico, A. E. Etiene, T. Paxton, A. Dell, M. Rogers, R. E. Sinden and
H. R. Morris, Nature, 1998, 289.
11-Chloro-11-(4-chlorophenyl)-2-methyl-6-phenyl-11H-indeno
[1,2-c]quinoline (6i). IR 3058.5, 2924.9, 2853.6, 1588.0, 1569.1,
1490.0, 1468.3, 1444.7, 1366.1 cm−1 1H NMR (400 MHz,
.
CDCl3) δ 8.14 (d, J = 8.8 Hz, 1H), 7.76–7.74 (m, 2H),
7.60–7.58 (m, 3H), 7.53–7.48 (m, 2H), 7.42–7.37 (m, 3H),
7.29–7.20 (m, 3H), 7.13–7.09 (m, 1H), 6.98 (d, J = 7.6 Hz, 1H),
2.43 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 154.8, 150.4,
147.3, 146.8, 139.9, 138.1, 137.4, 136.5, 134.2, 132.1, 130.1,
129.1, 129.0, 128.9, 128.8, 128.7, 128.6, 127.5, 124.8, 123.4,
123.1, 122.6, 67.0, 22.1. HRMS (ESI) calcd for C29H19Cl2N:
452.0973 (M + H+), found: 452.0971.
2,11-Dichloro-6-phenyl-11-(p-tolyl)-11H-indeno[1,2-c]quino-
line (6j). IR 3056.1, 2925.8, 2852.8, 1613.2, 1566.4, 1491.7,
1
1462.2, 1445.3, 1364.6 cm−1. H NMR (400 MHz, CDCl3) δ
8.15 (d, J = 9.2 Hz, 1H), 7.78–7.75 (m, 3H), 7.60–7.58 (m, 4H),
7.41 (d, J = 7.6 Hz, 1H), 7.33 (d, J = 8.0 Hz, 2H), 7.24–7.21
(m, 1H), 7.12–7.08 (m, 3H), 7.00 (d, J = 8.0 Hz, 1H), 2.31 (s,
3H). 13C NMR (100 MHz, CDCl3) δ 156.0, 151.9, 151.1, 146.4,
139.7, 138.3, 135.9, 135.7, 132.8, 131.9, 131.3, 130.5, 129.6,
129.2, 128.9, 128.8, 128.7, 125.8, 125.0, 123.4, 67.0, 21.0.
HRMS (ESI) calcd for C29H19Cl2N: 452.0973 (M + H+), found:
452.0983.
7 (a) A. K. Aggarwal and S. A. Jenekhe, Macromolecules, 1991, 24, 6806;
(b) X. Zhang, A. S. Shetty and S. A. Jenekhe, Macromolecules, 1999, 32,
7422; (c) S. A. Jenekhe, L. Lu and M. M. Alam, Macromolecules, 2001,
34, 7315.
8 For selected examples, see: (a) N. J. Clegg, S. Paruthiyil, D. C. Leitman
and T. S. Scanlan, J. Med. Chem., 2005, 48, 5989; (b) M. Lautens and
T. Marquardt, J. Org. Chem., 2004, 69, 4607; (c) H. Gao,
1974 | Org. Biomol. Chem., 2012, 10, 1969–1975
This journal is © The Royal Society of Chemistry 2012

View Online
J. A. Katzenellenbogen, R. Garg and C. Hansch, Chem. Rev., 1999, 99,
723.
(d) Y. Luo, X. Pan and J. Wu, Org. Lett., 2011, 13, 1150; (d) H. Ren,
Y. Luo, S. Ye and J. Wu, Org. Lett., 2011, 13, 2552; (e) S. Li, Y. Luo and
J. Wu, Org. Lett., 2011, 13, 3190; (f) Z. Chen, C. Ye, L. Gao and J. Wu,
Chem. Commun., 2011, 47, 5623; (g) Z. Chen and J. Wu, Org. Lett.,
2010, 12, 4856; (h) G. Qiu, Q. Ding, H. Ren, Y. Peng and J. Wu, Org.
Lett., 2010, 12, 3975; (i) Z. Chen, X. Yu and J. Wu, Chem. Commun.,
2010, 46, 6356; ( j) S. Ye, X. Yang and J. Wu, Chem. Commun., 2010,
46, 5238; (k) S. Ye, X. Yang and J. Wu, Chem. Commun., 2010, 46,
2950.
9 For selected examples, see: (a) J. Yang, M. V. Lakshmikantham and M.
P. Cava, J. Org. Chem., 2000, 65, 6739; (b) J. Barbera, O. A. Rakitin, M.
B. Ros and T. Torroba, Angew. Chem., Int. Ed., 1998, 37, 296;
(c) U. Akbulut, A. Khurshid, B. Hacioglu and L. Toppare, Polymer,
1990, 31, 1343.
10 For recent selected examples, see: (a) S. Li and J. Wu, Org. Lett., 2011,
13, 712; (b) Z. Chen, D. Zheng and J. Wu, Org. Lett., 2011, 13, 848;
This journal is © The Royal Society of Chemistry 2012
Org. Biomol. Chem., 2012, 10, 1969–1975 | 1975