One-pot three-component regioselective synthesis of C1-functionalised 3-arylbenzo[f]quinoline

Article abstract of DOI:10.1039/c5ra23413a

An efficient method for regioselective synthesis of C1-functionalised 3-arylbenzo[f]quinoline has been demonstrated via γ-selective aromatization using β-ketoester, 2-naphthylamine and aromatic aldehyde by employing 10 mol% camphorsulfonic acid as the cat

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One-pot three component regioselective synthesis of
C1-functionalised 3-arylbenzo[f]quinoline
Radhakrishna Gattu,a R. Sidick Basha,a Prasanta Ray Bagdia and Abu T. Khan*a,b
Received 00th January 20xx,
Accepted 00th January 20xx
An efficient method for C1-functionalised regioselective synthesis of 3-arylbenzo[f]quinoline has been demonstrated via δ-
selective inferred aromatization using β-ketoester, 2-naphthylamine and aromatic aldehyde by employing 10 mol%
camphorsulfonic acid as catalyst in acetonitrile at 70 °C. In this approach, two C-C bond formation will attain functionalised
benzo[f]quinoline in one-pot three component reaction. In addition, the present protocol access a diverse substrate scope
tolerance with good yields. Furthermore, the protocol was directly utilised for the synthesis of alkyl 2-(3-(naphthalen-2-
yl)benzo[f]quinolin-1-yl)acetate, allyl 2-(3-(heteroaromatic)benzo[f]quinolin-1-yl)acetate and functionalised 1,2,3-tri
substituted benzo[f]quinoline.
DOI: 10.1039/x0xx00000x
www.rsc.org/
applications demand the future bioactive scaffold of
functionalised benzoquinoline on development of facile
Introduction
A C4-functionalized quinoline are recognized as one of the
forefront of heterocycles1a that found in many alkaloid natural
products, bioactive scaffolds and in potent marketed drugs
(Figure 1).1b-e Around the active quinoline equip skeleton,2,1e
its integral core derive unit of benzoquinoline feature as
eminent biological probe in pharmaceuticals which viewed as
selective 5-HT3 receptor ligands,3 CFTR activators,4 D3
dopamine agonists,5 vesicular glutamate transporter
inhibitors,6 dopaminergic activity in nerve assay,7 α1-receptors
agonistic activity8 and in vitro human type 1 & 2 steroid 5α-
reductase inhibitors.9 Certainly, few of them are found to
possess antibacterial,10 antimicrobial,11 antipsychotic,12 and
antimalarial13 activities. These emerging wide avenue of
synthetic method. The design and synthesize of functionalised
benzoquinoline using -ketoester , 2-naphthylamine and an
aldehyde favours the possible reaction site-pathways as
shown in Scheme 1.
β
1
2
3
R2
O
O
O
O
O
O
Pathway A
Pathway B
OR1
Me
OR1
RHN
Me
OR1
R2CHO
3
R2C NR
R = 2-napthyl
R2
1
(imine)
A
E
n
C3 Aromatization
o
i
RNH2
2
t
Me
4
O
a
z
C3
i
t
R1O
a
O
3
O
O
m
C3 Ar omatization
o
R2
N
OR1
r
Me
OR1
2
A
C3
4
1
C
O
C
R2
NHR
2
OR1
R2
Me
1
O
R2
R = 2-napthyl
N
5
C1
1
C1
OR1
R2
B
C1 Aromatization
2
3
N
N
D
3
4
H
H
N
N
N
HO
HO
HO
Scheme 1. Possible reaction site-pathways.
-ketoester with aldehyde prefer to attain
H
O
O
In pathway
A, β
N
species
to and it may aromatize either at C3 or C1 position of the
napthylamine to form alkyl 4-methyl-2-arylbenzo[g]quinoline-
3-carboxylate and alkyl 1-methyl-3-arylbenzo[f]quinoline-2-
carboxylate . On the other hand in pathway , alkyl-5-
A which react with amine via Michael addition desires
N
N
Quinidine
Quinine
B
Cinchonidine
HO
N
HN
C
H
HO
H
D
B
N
HO
(naphthalen-2-ylamino)-3-oxo-5-arylpentanoate
E
prefer to
N
CF3
form alkyl 2-(3-arylbenzo[f] quinolin-1-yl)acetate
4
and alkyl 2-
I125
N3
HN
N
CF3
(2-arylbenzo[g]quinolin-4-yl)acetate
reaction site-pathways, the regioselective synthesis of alkyl 2-
(3-arylbenzo[f]quinolin-1-yl)acetate are highly desirable,
5. Among the possible
N
CF3
O
HO
Cinchonine
Mefloquine
IAAQ
4
which may act as a scaffold in drug discovery unit. Since the
reported methods in literature14 are limited, we were
interested to find out an elegant method for the synthesis of
Figure 1. Biologically active molecules containing C4-
functionalized quinoline skeleton.
functionalised benzo[f]quinoline
leading to the synthesis of alkyl 2-(3-arylbenzo[f]quinolin-1-
yl)acetate is shown in Scheme 2.
4. The insight schematic route
4
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Journal Name
O
yield. Subsequent reaction with tert-butyl acetoacetate (1c), 4-
fluorobenzaldehyde (3g)/furfural (3h) delivered the required
product 4g and 4h in 88% and 76% yield.
O
OR1
α
β
O
O
OR1
1
2 C-C
δ
Me
+
OR1
δ
3
R2
β
HO
α
N
R2
N
δ
β
-
selectivity
G
-ketoester
Table 1. Optimization of the reaction conditionsa
4
F
O
Scheme 2. Synthetic route and its pre-centre of alkyl 2-(3-
arylbenzo[f]quinolin-1-yl)acetate.
OEt
NH2
O
O
Catalyst
+
C6H5CHO
+
The role of δ-selectivity in synthetic precursor plays a vital key
transformation to obtain complex heterocycles15 in
pharmaceuticals.16 In particular, the δ-selective of
Me
OEt
Solvent, 70 °
C
N
3a
1a
2
4a
β-
Entry
Catalyst (mol%)
Solvent
Time (h)
Yield (%)b
ketoester17a,b through multicomponent reactions17c-f remains a
challenge puzzle to synthetic chemists. Multicomponent
reactions are often considered as sheer growing molecular
diversity18 to assemble complex molecules having diverse
range of biomedical applications.19 The existing demand in
these reactions is to achieve the significant biomolecular
scaffolds which widely access through intermolecular C-C bond
01
02
03
04
05
06
07
08
09
10
AcOH (10)
p-TSA (10)
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
DCE
8.0
12
55
NR
60
NR
92
80
89
35
65
25
Iodine (10)
L-Proline (10)
(±)-CSA (10)
(±)-CSA (05)
(±)-CSA (15)
(±)-CSA (10)
(±)-CSA (10)
(±)-CSA (10)
2.5
12
2.0
3.0
2.5
12
formation.20
We
envisaged
that
functionalised
benzo[f]quinoline may pursuit through progressive MCRs
intermolecular C-C bond formation.
THFc
06
The expedient cheap and readily available camphorsulfonic
acid has well-defined versatile application in organic
tranformations21 and it is used extensively in cyclisation
reactions,22 alkylation of anilines,23 asymmetric24 and in
natural product synthesis.25,22 We believed that driven
camphorsulfonic acid might be suitable for demanded δ-
selectivity in the regioselective synthesis of functionalised
benzo[f]quinoline.
n-BuOH
12
aAll the reactions were carried out using ethyl acetoacetate (1a, 0.5
equiv), 2-naphthylamine (2, 0.5 equiv) and benzaldehyde (3a, 0.5
equiv). bIsolated yield. cReaction temperature at 55°C. NR
reaction.
= no
Further, the reaction was examined with 2/3-
halobenzaldehyde (3i/3j)/2,4-dimethoxy benzaldehyde (3k), 2-
naphthylamine and methyl acetoacetate (1b) and the resultant
product 4i-k were obtained in 78-88% yield. In addition, 2/3-
Over all, herein we wish to report the efficient synthesis of C1-
(allyloxy) benzaldehyde (3l
acetoacetate 1d and 2-naphthylamine which gave the
corresponding product 4l and 4m in 74% and 76% yield
respectively. Reactions with different substituted
/3m) underwent reactions with allyl
functionalised 3-arylbenzo[f]quinoline from
β-ketoester, 2-
(
)
naphthylamine and aromatic aldehyde using 10 mol%
camphorsulfonic acid as catalyst in acetonitrile at 70 °C as
shown in Scheme 3.
O
benzaldehyde, ethyl acetoacetate (1a) and 2-naphthylamine
resulted in 4n-r in 72-90% yield.
SO3H
OR1
NH2
+
O
10 mol%
O
O
(±)
+
R2CHO
Me
OR1
CH3CN, 70 °
C
N
R2
1
3
2
4
Scheme 3. Synthesis of alkyl 2-(3-arylbenzo[f]quinolin-1-
yl)acetate.
Results and discussion
In attempt to optimise the reaction conditions, we had tested
a
series of reactions with ethyl acetoacetate 1a
, 2-
napthylamine 2 and benzaldehyde 3a as depicted in Table 1. It
is to be noted that the 10 mol% camphorsulfonic acid catalyst
in acetonitrile at 70 °C which gave best yield (Table 1, entry 5).
However, different solvents such as DCE, THF and n-BuOH
affords lower yield. (Table 1, entries 8-10). It is also
noteworthy that in our present protocol we have not observed
Figure 2. X-ray crystal of 4g
.
Inspired by these results, we performed reactions of allyl
acetoacetate (1d), 2-naphthylamine and with a variety of para-
substituted benzaldehyde such as 4-methyl (3b), 4-fluoro (3g
)
any other byproducts such as
medium. After optimisation, we conducted reactions with 2-
naphthylamine ( ), methyl acetoacetate (1b) and with a
diverse para-substituted benzaldehyde such as 4-methyl (3b),
4-chloro (3c), 4-bromo (3d), 4-methoxy (3e) and 4-hydroxy (3f
C, D and 5 in the reaction
and 4-methoxy (3e) under the optimized reaction condition
which afford the required benzo[f]quinolines 4s-u in 78-86%
yield as shown in Table 2. The crystal structure of 4g was
determined through single XRD analysis which is shown in
Figure 2.
2
)
moiety which afforded the desired product 4b-f in 86-96%
2 | J. Name., 2012, 00, 1-3
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Table
yl)acetate using (
2
.
Synthesis of alkyl 2-(3-arylbenzo[f]quinolin-1-
)-camphorsulfonic acid as catalysta,b
±
The protocol in hand was further investigated with
heteroaromatic aldehyde such as 1-benzyl-1,2,3-triazole-4-
carbaldehyde
(
8)/2-thiophenecarboxaldehyde
(9) with 2-
napthylamine (
2) and allyl acetoacetate (1d) using catalytic
amount of camphorsulfonic acid and the expected product
allyl 2-(3-(heteroaromatic)benzo[f]quinolin-1-yl)acetate 10 and
11 were obtained in 60% and 76% yield as shown in Scheme 5.
Scheme 5. Synthesis of allyl 2-(3-(heteroaromatic)benzo[f]quin
olin-1-yl)acetate.
Furthermore, we have synthesized the functionalised 1,2,3-
trisubstituted benzo[f]quinoline from ethyl 3-oxopentanoate
(
1e), 2-napthylamine (2) and 4-methoxybenzaldehyde (3e)
using 10 mol% camphorsulfonic acid in acetonitrile at 70 °C
which afford the resultant product 12 in 72% yield as shown in
Scheme 6.
Scheme 6. Synthesis of 1,2,3-trisubstituted benzo[f]quinoline.
A plausible mechanism is described as follows: The
β
most likely to react with camphorsulfonic acid to form an
-ketoester
1
intermediate I, which subsequently undergoes rearrangement
and reacts with the generated imine to form a Michael type
addition product from δ-selective of -ketoester with imine via
II17a to attain III. Further, III favors to prefer aromatization to
form the desired product as shown in Scheme 7. It is to be
aAll the reactions were carried out using β-ketoester (0.5 equiv), 2-
naphthylamine (0.5 equiv), and aromatic aldehyde (0.5 equiv). bIsolated
yield.
β
4
We have also performed reaction with fused aromatic
aldehyde such as 2-napthaldehyde (
with different -ketoesters in the presence of 10 mol%
camphorsulfonic acid as catalyst in acetonitrile at 70 °C and
the desired product alkyl 2-(3-(naphthalen-2-
was obtained in good yield
6), 2-napthylamine (2) and
β
yl)benzo[f]quinolin-1-yl)acetate
7
as shown in Scheme 4.
Scheme 7. Proposed mechanism for the formation of alkyl 2-
(3-arylbenzo[f]quinolin-1-yl)acetate
.
Scheme 4. Synthesis of alkyl 2-(3-(naphthalen-2-yl)benzo[f]
quinolin-1-yl)acetate.
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highlighted here, that we have observed the HRMS of the Methyl
Journal Name
2-(3-(4-chlorophenyl)benzo[f]quinolin-1-yl)acetate
intermediate III of 4p after 10 min under reflux condition (4c):14a Yield 94%, white solid, mp 138-139 ˚C,1H NMR (400
which indirectly support the proposed mechanism (see MHz, CDCl3): δ 8.49 (d, J = 7.2 Hz, 1H), 8.17 (d, J = 8.8 Hz, 2H),
supporting information).
8.12 (d, J = 8.8 Hz, 1H), 8.00-7.96 (m, 2H), 7.83 (s, 1H), 7.69-
7.66 (m, 2H), 7.51 (d, J = 8.8 Hz, 2H), 4.51 (s, 2H), 3.78 (s, 3H);
13C NMR (100 MHz, CDCl3): δ 171.1, 154.3, 149.9, 141.4, 137.0,
135.9, 133.2, 131.9, 129.7, 129.5, 129.2, 128.9, 127.2, 127.0,
126.8, 124.7, 122.9, 52.8, 43.7; IR (KBr)νmax 3056, 2942, 2924,
2852, 1741, 1585, 1550, 1481, 1435, 1390, 1328, 1257, 1198,
1157, 1091, 1012 cm-1; HRMS (ESI) Calcd For C22H17ClNO2
362.0943 (M + H+); Found 362.0942.
Conclusions
In summary, the regioselective synthesis of alkyl 2-(3-
arylbenzo[f]quinolin-1-yl)acetate has been achieved using
camphorsulfonic acid through δ-selective of β-ketoester. It is a
straight forward methodology which provide flexible access to
diverse range of substrates. The prominent aspect of this
present method was that two new C-C bonds were formed in a
one-pot fashion under mild reaction conditions. In addition,
the protocol enables the synthesis of naphthalen-2-yl, hetero
aromatic and trisubstituted benzo[f]quinoline analogues in
good yields.
Methyl
2-(3-(4-bromophenyl)benzo[f]quinolin-1-yl)acetate
(4d):14a Yield 92%, light yellow solid, mp 143-144 ˚C,1H NMR
(400 MHz, CDCl3): δ 8.51 (d, J = 9.0 Hz, 1H), 8.11 (d, J = 8.4 Hz,
2H), 8.06 (d, J = 9.0 Hz, 1H), 7.99- 7.96 (m, 2H), 7.83 (s, 1H),
7.68-7.66 (m, 4H), 4.51 (s, 2H), 3.78 (s, 3H); 13C NMR (100 MHz,
CDCl3): δ 171.2, 154.5, 150.3, 141.1, 137.9, 133.2, 132.2, 131.7,
129.8, 129.6, 129.5, 129.1, 127.1, 126.9, 126.8, 124.7, 124.1,
122.7, 52.8, 43.6; IR (KBr)νmax 3051, 2951, 2915, 2854, 1736,
1584, 1549, 1481, 1455, 1434, 1387, 1356, 1328, 1257, 1199,
1159, 1087, 1008 cm-1; HRMS (ESI) Calcd For C22H17BrNO2
406.0437 (M + H+); Found 406.0437.
General Procedure
Synthesis of alkyl 2-(3-arylbenzo[f]quinolin-1-yl)acetate (4)
A mixture of
β
0.5 mmol) and aromatic aldehyde (
-ketoester (
1
, 0.5 mmol), 2-naphthylamine (
2,
3, 0.5 mmol) was taken in 5
Methyl 2-(3-(4-methoxyphenyl)benzo[f]quinolin-1-yl)acetate
(4e): Yield 86%, light yellow solid, mp 149-150 ˚C, 1H NMR (600
MHz, CDCl3): δ 8.47 (d, J = 8.4 Hz, 1H), 8.18 (d, J = 8.4 Hz, 2H),
8.09 ( d, J = 9.0 Hz, 1H), 7.93 (t, J = 9.0 Hz, 2H), 7.78 (s, 1H),
7.65-7.56 (m, 2H), 7.04 (d, J = 8.4 Hz, 2H), 4.46 (s, 2H), 3.87 (s,
3H), 3.76 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 171.2, 161.1,
155.3, 149.9, 140.9, 132.9, 131.8, 131.5, 131.2, 129.9, 129.4,
128.9, 126.8, 126.7, 126.6, 124.1, 122.7, 114.4, 55.5, 52.7,
43.6; IR (KBr)νmax 3068, 2995, 2948, 2937, 2830, 1737, 1604,
1544, 1503, 1434, 1354, 1337, 1252, 1202, 1183, 1161, 1028
cm-1; HRMS (ESI) Calcd For C23H20NO3 358.1438 (M + H+);
Found 358.1430.
ml acetonitrile. To that camphorsulfonic acid (0.011g, 0.05
mmol) was added in to it and it allow to stir at 70 °C. After
completion of the reaction, the solvent was removed under
reduced pressure and it was extract with DCM, washed with
water, dried over sodium sulphate and concentrate under
reduced pressure. Then, the residue was purified through
column chromatography to obtain the pure product
Similarly, the compound and 10 12 were synthesized by
following the above reaction procedure.
4.
7
-
Ethyl 2-(3-phenylbenzo[f]quinolin-1-yl)acetate (4a): Yield
92%, white solid, mp 131-132 ˚C,1H NMR (400 MHz, CDCl3): δ
8.54 (d, J = 8.8 Hz, 1H), 8.22 (d, J = 8.8 Hz, 2H), 8.09 (d, J = 9.2
Hz, 1H), 7.99- 7.97 (m, 2H), 7.87 (s, 1H), 7.67-7.64 (m, 2H), 7.56
(t, J = 7.2 Hz, 2H), 7.49 (t, J = 6.8 Hz, 1H), 4.49 (s, 2H), 4.25 (q, J
= 7.2 Hz, 2H), 1.23 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz,
CDCl3): δ 170.8, 155.9, 150.3, 141.1, 139.2, 133.2, 131.5, 130.0,
129.8, 129.5, 129.4, 129.1, 127.6, 127.0, 126.9, 126.8, 124.6,
123.2, 61.7, 44.0, 14.4; IR (KBr)νmax 3056, 2980, 2902, 1735,
1584, 1552, 1484, 1455, 1391, 1367, 1322, 1255, 1194, 1156,
1029 cm-1; HRMS (ESI) Calcd For C23H20NO2 342.1489 (M + H+);
Found 342.1489.
Methyl 2-(3-(4-hydroxyphenyl)benzo[f]quinolin-1-yl)acetate
(4f): Yield 90%, white solid, mp 141-142 ˚C, 1H NMR (600 MHz,
CDCl3): δ 9.30 (s, 1H), 8.40 (d, J = 6.0 Hz, 1H), 8.02 (d, J = 6.6
Hz, 2H), 7.93 (d, J = 2.4, 1H), 7.92 (d, J = 1.8 Hz, 2H), 7.75 (s,
1H), 7.56-7.53 (m, 2H), 6.91 (d, J = 6.0 Hz, 2H), 4.44 (s, 2H),
3.69 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 170.4, 158.5, 154.8,
149.2, 140.1, 132.0, 129.1, 129.0, 128.6, 128.5, 128.1, 128.0,
126.1, 125.9, 125.7, 122.9, 121.8, 121.7, 115.4, 115.3, 51.8,
42.8; IR (KBr)νmax 3058, 2995, 2953, 2838, 1738, 1608, 1588,
1549, 1514, 1484, 1451, 1353, 1258, 1171, 1130, 1058 cm-1;
HRMS (ESI) Calcd For C22H18NO3 344.1281 (M + H+); Found
344.1286.
Methyl 2-(3-(p-tolyl)benzo[f]quinolin-1-yl)acetate (4b):14a
Yield 96%, light yellow, mp 168-169 ˚C,1H NMR (400 MHz,
CDCl3): δ 8.49 (d, J = 7.6 Hz, 1H), 8.12 (t, J = 8.0 Hz, 2H), 8.08 (s,
1H), 7.97-7.93 (m, 2H), 7.83 (s, 1H), 7.68-7.61 (m, 2H), 7.35 (d,
J = 8.0 Hz, 2H), 4.47 (s, 2H), 3.77 (s, 3H), 2.45 (s, 3H); 13C NMR
(100 MHz, CDCl3): δ 171.3, 155.8, 150.2, 140.8, 139.6, 136.2,
133.1, 131.4, 129.9, 129.7, 129.6, 129.4, 128.2, 127.5, 126.8,
126.7, 124.3, 122.9, 52.7, 43.7, 21.5; IR (KBr)νmax 3029, 2952,
2922, 2853, 1737, 1579, 1548, 1481, 1452, 1437, 1392, 1353,
1259, 1184, 1132, 1057 cm-1; HRMS (ESI) Calcd For C23H20NO2
342.1489 (M + H+); Found 342.1505.
Tert-butyl 2-(3-(4-fluorophenyl)benzo[f]quinolin-1-yl)acetate
(4g): Yield 88%, white solid, mp 140-141 ˚C,1H NMR (600 MHz,
CDCl3): δ 8.58 (d, J = 7.8 Hz, 1H), 8.23-8.21 (m, 2H), 8.06 (d, J =
8.4 Hz, 1H), 7.98-7.95 (m, 2H), 7.81 (s, 1H), 7.67-7.64 (m, 2H),
7.23-7.20 (m, 2H), 4.41 (s, 2H), 1.44 (s, 9H); 13C NMR (150 MHz,
CDCl3): δ 169.5, 165.2, 163.5, 154.1, 133.5, 133.1, 131.2, 131.1,
130.3, 130.1, 129.7, 129.6, 129.3, 128.3, 127.3, 127.2, 127.1,
127.0, 126.6, 124.8, 123.6, 116.3, 116.1, 115.6, 115.5, 82.6,
45.6, 28.2; IR (KBr)νmax 3057, 2976, 2927, 2850, 1727, 1602,
4 | J. Name., 2012, 00, 1-3
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1585, 1553, 1532, 1510, 1483, 1455, 1392, 1368, 1329, 1226, 17.2 Hz, 1H), 5.26 (d, J = 13.6 Hz, 2H), 5.22-5.18 (m 1H), 4.67-
1149, 1073, 1014 cm-1; HRMS (ESI) Calcd For C25H23FNO2 4.63 (m, 4H), 4.51 (s, 2H); 13C NMR (100 MHz, CDCl3): δ 170.5,
388.1708 (M + H+); Found 388.1707.
156.5, 155.1, 150.1, 139.3, 133.3, 133.1, 131.8, 131.7, 131.0,
130.5, 129.9, 129.7, 129.3, 129.2, 127.8, 126.8, 126.7, 126.6,
124.2, 121.7, 118.9, 117.2, 113.3, 69.5, 66.1, 43.8; IR (KBr)νmax
3055, 2969, 2948, 2930, 2835, 1741, 1687, 1624, 1577, 1544,
1480, 1451, 1352, 1316, 1257, 1224, 1182, 1148, 1059 cm-1;
HRMS (ESI) Calcd For C27H24NO3 410.1751 (M + H+); Found
410.1755.
Tert-butyl 2-(3-(furan-2-yl)benzo[f]quinolin-1-yl)acetate (4h):
Yield 76%, brown solid, mp 94-95 ˚C, 1H NMR (400 MHz,
CDCl3): δ 8.56 (d, J = 8.4 Hz, 1H), 8.04 (d, J = 9.2 Hz, 1H), 7.96-
7.95 (m, 3H), 7.84 (s, 1H), 7.66-7.64 (m, 2H), 7.27 (d, J = 3.2 Hz,
1H), 6.62-6.61 (m, 1H), 4.41 (s, 2H), 1.43 (s, 9H); 13C NMR (150
MHz, CDCl3): δ 169.8, 153.6, 150.2, 147.8, 144.1, 141.7, 133.1,
131.6, 129.4, 129.4, 126.9, 126.8, 126.7, 124.6, 121.6, 112.4, allyl
2-(3-(3-(allyloxy)phenyl)benzo[f]quinolin-1-yl)acetate
1
110.0, 82.2, 45.3, 28.2; IR (KBr)νmax 3029, 2974, 2926, 1728, (4m): Yield 76%, white solid, mp 81-82 ˚C, H NMR (600 MHz,
1601, 1551, 1491, 1454, 1393, 1368, 1325, 1254, 1224, 1072 CDCl3): δ 8.53 (d, J = 6.0 Hz, 1H), 8.08 (d, J = 6.0 Hz, 1H), 7.98-
cm-1; HRMS (ESI) Calcd For C23H22NO3 360.1594 (M + H+); 7.95 (m, 2H), 7.86-7.84 (m, 2H), 7.76 (d, J = 6.0 Hz, 1H), 7.66-
Found 360.1609.
7.63 (m, 2H), 7.44 (t, J = 6.0 Hz, 1H), 7.04 (d, J = 6.0 Hz, 1H),
6.17-6.10 (m, 1H), 5.92-5.85 (m, 1H), 5.49 (d, J = 18.0 Hz, 1H),
5.33 (d, J = 6.0 Hz, 1H), 5.28 (d, J = 18.0 Hz, 1H), 5.22 (d, J =
12.0 Hz, 1H), 4.68 (d, J = 6.0 Hz, 4H), 4.52 (s, 2H)); 13C NMR
(150 MHz, CDCl3): δ 170.4, 159.4, 155.6, 150.2, 140.8, 140.5,
133.5, 133.2, 131.8, 131.5, 130.0, 129.9, 129.7, 129.4, 126.9,
126.8, 126.8, 124.7, 123.3, 120.2, 119.1, 117.9, 116.3, 113.7,
69.2, 66.3, 43.8; IR (KBr)νmax 3056, 2924, 2896, 1733, 1647,
1583, 1552, 1488, 1455, 1423, 1358, 1319, 1281, 1231, 1195,
1154, 1024, 991 cm-1; HRMS (ESI) Calcd For C27H24NO3
410.1756 (M + H+); Found 410.1754.
Methyl
2-(3-(2-chlorophenyl)benzo[f]quinolin-1-yl)acetate
(4i): Yield 88%, brown solid, mp 79-80 ˚C,1H NMR (400 MHz,
CDCl3): δ 8.56 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 8.00 (t,
J = 8.4 Hz, 2H), 7.84 (s, 2H), 7.69 (s, 2H), 7.53 (d, J = 7.2 Hz, 1H),
7.42 (t, J = 8.4 Hz, 2H), 4.52 (s, 2H), 3.77 (s, 3H); 13C NMR (100
MHz, CDCl3): δ 170.9, 155.0, 149.4, 133.3, 132.7, 132.3, 132.2,
130.4, 129.6, 128.6, 127.5, 127.4, 127.2, 127.1, 126.9, 124.8,
52.8, 43.6; IR (KBr)νmax 3059, 2987, 2953, 2850, 1738, 1596,
1580, 1550, 1476, 1435, 1395, 1351, 1330, 1258, 1201, 1160,
1094, 1057 cm-1; HRMS (ESI) Calcd For C22H17ClNO2 362.0943
(M + H+); Found 362.0943.
Ethyl 2-(3-(p-tolyl)benzo[f]quinolin-1-yl)acetate (4n): Yield
1
90%, brown solid, mp 102-103 ˚C, H NMR (400 MHz, CDCl3): δ
Methyl
2-(3-(3-bromophenyl)benzo[f]quinolin-1-yl)acetate
8.53 (d, J = 8.0 Hz, 1H), 8.13 (d, J = 8.4 Hz, 2H), 8.08 (s, 1H),
7.96 (d, J = 9.6 Hz, 2H), 7.85 (s, 1H), 7.67-7.63 (m, 2H), 7.34 (d,
J = 7.6 Hz, 2H), 4.48 (s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 2.45 (s, 3H),
1.23 (t, J = 6.8 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 170.8,
155.8, 150.2, 141.1, 139.7, 136.2, 133.1, 131.4, 130.0, 129.8,
129.7, 129.4, 127.5, 126.9, 126.8, 126.7, 124.4, 123.0, 61.7,
43.9, 21.6, 14.4; IR (KBr)νmax 3053, 3025, 2980, 2923, 2855,
1734, 1606, 1585, 1550, 1512, 1482, 1455, 1391, 1366, 1322,
1248, 1217, 1184, 1156, 1094, 1054 cm-1; HRMS (ESI) Calcd
For C24H22NO2 356.1645 (M + H+); Found 356.1646.
1
(4j): Yield 84%, white solid, mp 130-131 ˚C, H NMR (400 MHz,
CDCl3): δ 8.50 (d, J = 12.0 Hz, 1H), 8.40 (s, 1H), 8.12 (d, J = 12.0
Hz, 1H), 8.06 (d, J = 12.0 Hz, 1H), 7.97 (d, J = 12.0 Hz, 2H),
7.81(s, 1H), 7.69-7.65 (m, 2H), 7.59 (d, J = 12.0 Hz, 1H), 7.39 (t,
J = 12.0 Hz, 1H), 4.49 (s, 2H), 3.78 (s, 3H); 13C NMR (100 MHz,
CDCl3): δ 171.4, 154.1, 150.3, 141.1, 141.0, 133.3, 132.4, 131.8,
130.6, 130.5, 129.8, 129.6, 129.5, 127.1, 126.9, 126.8, 126.1,
124.9, 123.3, 122.9, 52.8, 43.7; IR (KBr)νmax 3031, 2950, 2916,
2848, 1724, 1605, 1582, 1549, 1488, 1454, 1424, 1383, 1357,
1323, 1306, 1247, 1161, 1053 cm-1; HRMS (ESI) Calcd For
C22H17BrNO2 406.0437 (M + H+); Found 406.0435.
Ethyl
2-(3-(4-methoxyphenyl)benzo[f]quinolin-1-yl)acetate
(4o): Yield 80%, white solid, mp 120-121 ˚C, 1H NMR (600 MHz,
CDCl3): δ 8.53 (d, J = 6.0 Hz, 1H), 8.19 (d, J = 6.0 Hz, 2H), 8.06
(d, J = 12.0 Hz, 1H), 7.96 (d, J = 6.0 Hz, 1H), 7.95-7.94 (m, 1H),
7.81 (s, 1H), 7.66-7.63 (m, 2H), 7.07 (d, J = 6.0 Hz, 2H), 4.48 (s,
2H), 4.24 (q, J = 6.0 Hz, 2H), 3.90, (s, 3H), 1.23 (t, J = 6.0 Hz,
3H); 13C NMR (150 MHz, CDCl3): δ 170.8, 161.0, 155.5, 150.2,
140.9, 133.0, 131.7, 131.3, 130.1, 129.7, 129.4, 128.9, 126.8,
126.7, 126.7, 124.1, 122.6, 114.4, 61.7, 55.6, 44.0, 14.4; IR
(KBr)νmax 3027, 2957, 2924, 2852, 1732, 1631, 1606, 1583,
1550, 1531, 1512, 1482, 1455, 1392, 1364, 1324, 1248, 1224,
1175, 1145, 1030 cm-1; HRMS (ESI) Calcd For C24H22NO3
372.1594 (M + H+); Found 372.1594.
Methyl 2-(3-(2,4-dimethoxyphenyl)benzo[f]quinolin-1-yl)ace
tate (4k): Yield 78%, brown solid, mp 111-112 ˚C, 1H NMR (400
MHz, CDCl3): δ 8.52 (d, J = 7.6 Hz, 1H), 8.12 (d, J = 8.0 Hz, 1H),
8.02-7.94 (m, 4H), 7.64 (s, 2H), 6.69 (d, J = 6.8 Hz, 1H), 6.60 (s,
1H), 4.49 (s, 2H), 3.87 (s, 6H), 3.75 (s, 3H); 13C NMR (100 MHz,
CDCl3): δ 171.3, 162.1, 158.8, 154.6, 149.7, 139.8, 133.0, 132.7,
131.2, 129.9, 129.4, 129.2, 127.3, 126.7, 123.9, 105.7, 99.2,
55.9, 55.7, 52.6, 43.7; IR (KBr)νmax 3059, 3003, 2950, 2837,
1736, 1608, 1579, 1547, 1505, 1455, 1437, 1300, 1283, 1209,
1160, 1030 cm-1; HRMS (ESI) Calcd For C24H22NO4 388.1544 (M
+ H+); Found 388.1542.
allyl
2-(3-(2-(allyloxy)phenyl)benzo[f]quinolin-1-yl)acetate
Ethyl 2-(3-(2-fluorophenyl)benzo[f]quinolin-1-yl)acetate (4p):
1
Yield 72%, semisolid, H NMR (600 MHz, CDCl3): δ 8.57 (d, J =
(4l): Yield 74%, light yellow solid, mp 169-170 ˚C, 1H NMR (400
MHz, CDCl3): δ 8.55 (d, J = 8.0 Hz, 1H), 8.17 (s, 1H), 8.07 (s, 1H),
8.04 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.4 Hz, 2H), 7.66-7.64 (m,
2H), 7.42 (t, J = 7.6 Hz, 1H), 7.17 (t, J = 7.6 Hz, 1H), 7.04 (d, J =
8.4 Hz, 1H), 6.09-6.00 (m, 1H), 5.91-5.81 (m, 1H), 5.38 (d, J =
6.0 Hz, 1H), 8.24-8.21 (m, 1H), 8.08 (d, J = 6.0 Hz, 1H), 7.98 (d, J
= 6.0Hz, 2H), 7.97-7.95 (m, 1H), 7.68-7.66 (m, 2H), 7.43 (t, J =
6.0 Hz, 1H), 7.34 (t, J = 6.0 Hz, 1H), 7.23-7.20, (m, 1H), 4.50 (s,
2H), 4.24 (q, J = 6.0Hz, 2H), 1.23 (t, J = 6.0 Hz, 3H); 13C NMR
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J. Name., 2013, 00, 1-3 | 5

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DOI: 10.1039/C5RA23413A
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(150 MHz, CDCl3): δ 170.7, 161.9, 160.2, 152.2, 150.2, 140.7, 1585, 1552, 1508, 1483, 1454, 1390, 1358, 1322, 1228, 1191,
133.3, 131.6, 131.6, 131.5, 131.1, 131.0, 129.9, 129.6, 129.4, 1156, 1014 cm-1; HRMS (ESI) Calcd For C24H19FNO2 372.1395
127.1, 127.0, 126.8, 124.9, 124.9, 124.7, 116.6, 116.4, 61.7, (M + H+); Found 372.1384.
44.0, 14.3; IR (KBr)νmax 3028, 2956, 2923, 2852, 1733, 1586,
Allyl
2-(3-(4-methoxyphenyl)benzo[f]quinolin-1-yl)acetate
1582, 1550, 1484, 1452, 1371, 1364, 1320, 1249, 1215, 1155,
1080, 1030 cm-1; HRMS (ESI) Calcd For C23H19FNO2 360.1395
(M + H+); Found 360.1396.
1
(4u): Yield 78%, pale yellow solid, mp 92-95 ˚C, H NMR (400
MHz, CDCl3): δ 8.50 (d, J = 6.4 Hz, 1H) 8.18 (d, J = 8.0 Hz, 2H),
8.05 (d, J = 9.2 Hz, 1H), 7.95 (d, J = 7.6 Hz, 2H), 7.81 (s, 1H),
Ethyl 2-(3-(2-chlorophenyl)benzo[f]quinolin-1-yl)acetate (4q): 7.62 (d, J = 3.2 Hz, 2H), 7.05 (d, J = 8.0 Hz, 2H), 5.89-5.85 (m,
Yield 82%, white solid, mp 151-152 ˚C, 1H NMR (600 MHz, 1H), 5.31-5.21 (m, 2H), 4.68 (s, 2H), 4.49 (s, 2H), 3.89 (s, 3H);
CDCl3): δ 8.60 (d, J = 8.4 Hz, 1H), 8.12 (d, J = 7.2 Hz, 1H), 8.01- 13C NMR (150 MHz, CDCl3): δ 170.5, 161.0, 155.4, 150.2, 140.6,
7.97 (m, 2H), 7.83-7.81 (m, 2H), 7.70-7.67 (m, 2H), 7.53 (d, J = 133.0, 131.8, 131.6, 131.3, 129.9, 129.6, 129.3, 128.9, 126.7,
7.8 Hz, 1H), 7.45-7.31 (m, 1H), 7.43-7.38 (m, 1H), 4.49 (s, 2H), 126.6, 124.1, 122.6, 119.0, 114.4, 66.1, 55.5, 43.8; IR (KBr)νmax
4.24 (q, J = 7.2 Hz, 2H), 1.23 (t, J = 7.2 Hz, 3H); 13C NMR (100 3051, 2959, 2933, 2836, 1735, 1675, 1653, 1606, 1583, 1550,
MHz, CDCl3): δ 170.4, 155.9, 149.3, 133.2, 132.7, 132.3, 132.1, 1530, 1511, 1482, 1455, 4140, 1358, 1323, 1306, 1176, 1155,
130.5, 130.4, 129.7, 129.6, 129.5, 128.6, 127.5, 127.4, 127.3, 1111, 1030 cm-1; HRMS (ESI) Calcd For C25H22NO3 384.1594 (M
127.1, 124.9, 61.8, 43.9, 14.3; IR (KBr)νmax 3060, 2982, 2933, + H+); Found 384.1612.
2849, 1734, 1627, 1596, 1578, 1550, 1475, 1442, 1394, 1369,
Ethyl
2-(3-(naphthalen-2-yl)benzo[f]quinolin-1-yl)acetate
1350, 1330, 1244, 1210, 1160, 1133, 1094, 1055, 1038 cm-1;
HRMS (ESI) Calcd For C23H19ClNO2 376.1099 (M + H+); Found
376.1099.
1
(7a): Yield 74%, pale yellow solid, mp 76-77 ˚C, H NMR (400
MHz, CDCl3): δ 8.69 (s, 1H), 8.56 (d, J = 8.8 Hz, 1H), 8.41 (d, J =
8.4 Hz, 1H), 8.18 (d, J = 8.8 Hz, 1H), 8.03-8.02 (m, 3H), 8.00-
Ethyl 2-(3-(3-bromophenyl)benzo[f]quinolin-1-yl)acetate (4r): 7.96 (m, 2H), 7.92-7.89 (m, 1H), 7.69-7.64 (m, 2H), 7.55-7.53
Yield 82%, white solid, mp 125-126 ˚C, 1H NMR (600 MHz, (m, 2H), 4.54 (s, 2H), 4.27 (q, J = 7.2 Hz, 2H), 1.25 (t, J =7.2 Hz,
CDCl3): δ 8.54 (d, J = 12.0 Hz, 1H), 8.40 (s, 1H), 8.13 (d, J = 6.0 3H); 13C NMR (100 MHz, CDCl3): δ 170.8, 155.6, 150.2, 141.4,
Hz, 1H), 8.07 (d, J = 6.0 Hz, 1H), 8.00-7.97, (m, 2H), 7.84 (s, 1H), 136.2, 134.1, 133.7, 133.2, 131.7, 130.0, 129.5, 129.4, 129.1,
7.68-7.66 (m, 2H), 7.60 (d, J = 6.0 Hz, 1H), 7.41 (t, J = 12.0 Hz, 128.8, 127.9, 127.3, 127.0, 126.9, 126.9, 126.8, 126.5, 125.1,
1H), 4.50 (s, 2H), 4.25 (q, J = 6.0 Hz, 2H), 1.25 (t, J = 6.0 Hz, 3H); 124.7, 123.5, 61.7, 44.1, 14.4; IR (KBr)νmax 3056, 2978, 2923,
13C NMR (150 MHz, CDCl3): δ 170.7, 154.2, 150.2, 141.4, 141.1, 2851, 1734, 1583, 1552, 1509, 1482, 1452, 1389, 1367, 1321,
133.3, 132.5, 131.7, 130.7, 130.6, 129.9, 129.6, 129.4, 126.9, 1256, 1215, 1195, 1156, 1029; cm-1; HRMS (ESI) Calcd For
126.2, 126.1, 124.9, 123.4, 123.1, 123.0, 61.5, 43.9, 13.9; IR C27H22NO2 392.1645 (M + H+); Found 392.1648.
(KBr)νmax 3025, 2922, 2852, 1733, 1586, 1572, 1550, 1480,
Methyl 2-(3-(naphthalen-2-yl)benzo[f]quinolin-1-yl)acetate
1452, 1442, 1428, 1371, 1322, 1213, 1197, 1158, 1019 cm-1;
1
(7b): Yield 87%, white solid, mp 80-81 ˚C, H NMR (600 MHz,
HRMS (ESI) Calcd For C23H19BrNO2 420.0594 (M + H+); Found
CDCl3): δ 8.68 (s, 1H), 8.52 (d, J = 6.0 Hz, 1H), 8.41-8.39 (m,
420.0623.
1H), 8.14 (d, J = 6.0 Hz, 1H), 8.02-8.01 (m, 4H), 7.99-7.96 (m,
Allyl 2-(3-(p-tolyl)benzo[f]quinolin-1-yl)acetate (4s): Yield 1H), 7.90 (t, J = 6 Hz, 1H), 7.68-7.65 (m, 2H), 7.55-7.53 (m, 2H),
1
80%, brown solid, mp 83-84 ˚C, H NMR (400 MHz, CDCl3): δ 4.54 (s, 2H), 3.79 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 171.3,
8.52 (d, J = 8.8 Hz, 1H), 8.12 (d, J = 8.0 Hz, 2H), 8.08 (d, J = 9.2 155.6, 150.3, 141.0, 136.3, 134.1, 133.7, 133.2, 131.6, 129.9,
Hz, 1H), 7.99-7.95 (m, 2H), 7.86 (s, 1H), 7.69-7.63 (m, 2H), 7.35 129.6, 129.4, 129.0, 128.8, 127.9, 127.2, 127.0, 126.9, 126.8,
(d, J = 8.0 Hz, 2H), 5.92-5.83 (m, 1H), 5.30-5.17 (m, 2H), 4.68 126.8, 126.6, 125.1, 124.6, 123.4, 52.8, 43.7; IR (KBr)νmax 3057,
(d, J = 5.2 Hz, 2H), 4.52 (s, 2H), 2.45 (s, 3H); 13C NMR (100 MHz, 2986, 2952, 2848, 1736, 1595, 1549, 1472, 1432, 1391, 1347,
CDCl3): δ 170.4, 155.8, 150.2, 140.7, 139.6, 136.2, 133.1, 131.8, 1198, 1158, 1088, 1055 cm-1; HRMS (ESI) Calcd For C26H20NO2
131.4, 130.0, 129.8, 129.4, 128.7, 127.5, 126.8, 124.4, 122.9, 378.1489 (M + H+); Found 378.1486.
119.0, 66.2, 43.8, 21.5; IR (KBr)νmax 3062, 3035, 2923, 2853,
Allyl 2-(3-(1-benzyl-1H-1,2,3-triazol-4-yl)benzo[f]quinolin-1-
1735, 1653, 1605, 1582, 1548, 1479, 1451, 1352, 1330, 1274,
yl)acetate (10): Yield 60%, brown solid, mp 124-125 ˚C, 1H
1216, 1185, 1154, 1130, 1054 cm-1; HRMS (ESI) Calcd For
NMR (600 MHz, CDCl3): δ 8.53 (d, J = 8.1 Hz, 1H), 8.45 (s, 1H),
C25H22NO2 368.1645 (M + H+); Found 368.1649.
8.02-7.97 (m, 2H), 7.69 (s, 2H), 7.40-7.39 (m, 6H), 7.28 (s, 1H),
Allyl 2-(3-(4-fluorophenyl)benzo[f]quinolin-1-yl)acetate (4t): 5.86-5.83 (m, 1H), 5.65 (s, 2H), 5.26 (d, J = 17.4 Hz, 1H), 5.20
Yield 86%, white solid, mp 154-155 ˚C, 1H NMR (600 MHz, (d, J = 10.8 Hz, 1H), 4.66 (d, J = 5.6 Hz, 2H), 4.57 (s, 2H); 13C
CDCl3): δ 8.52-8.51 (m, 1H), 8.22-8.20 (m, 2H), 8.09 (d, J = 8.4 NMR (150 MHz, CDCl3): δ 170.3, 150.2, 148.9, 148.7, 141.3,
Hz, 1H), 7.98-7.95 (m, 2H), 7.83 (s, 1H), 7.67-7.63 (m, 2H), 7.22 134.7, 133.2, 131.8, 131.7, 130.1, 129.4, 129.1, 129.0, 128.5,
(t, J = 8.4 Hz , 2H), 5.92-5.85 (m, 1H), 5.29 (t, J = 8.4 Hz, 1H), 128.1, 127.0, 126.8, 125.3, 123.4, 123.1, 122.9, 119.1, 66.3,
5.23 (d, J = 11.4 Hz, 1H), 4.69 (d, J = 6.0 Hz, 2H), 4.52 (s, 2H); 54.7, 43.9; IR (KBr)νmax 3148, 3062, 2924, 2853, 1736, 1647,
13C NMR (150 MHz, CDCl3): δ 170.3, 164.9, 163.3, 154.6, 150.0, 1597, 1557, 1497, 1454, 1430, 1362, 1338, 1296, 1232, 1187,
141.2, 133.2, 131.8, 131.7, 129.8, 129.6, 129.5, 129.5, 129.3, 1156, 1092, 1043, 1017 cm-1; HRMS (ESI) Calcd For C27H23N4O2
127.0, 126.9, 126.8, 124.5, 122.9, 119.2, 116.1, 115.9, 66.3, 435.1821 (M + H+); Found 435.1813.
43.8; IR (KBr)νmax 3059, 2954, 2924, 2848, 1735, 1653, 1601,
6 | J. Name., 2012, 00, 1-3
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4
5
M. Murthy, N. Pedemonte, L. MacVinish, L. Galietta and A.
Cuthbert, Eur. J. Pharmacol., 2005, 516, 118.
Allyl 2-(3-(thiophen-2-yl)benzo[f]quinolin-1-yl)acetate (11):
Yield 76%, brown solid, mp 114-115 ˚C, 1H NMR (600 MHz,
CDCl3): δ 8.48 (d, J = 9.6 Hz, 1H), 8.01 (d, J = 9.0 Hz, 1H), 7.95-
7.93 (m, 2H), 7.78 (s, 1H), 7.76 (d, J = 3.4 Hz, 1H), 7.65-7.61 (m,
2H), 7.47 (d, J = 5.4 Hz, 1H), 7.18-7.16 (m, 1H), 5.91-5.84 (m,
1H), 5.29-5.26 (m, 1H), 5.22 (d, J = 9.6 Hz, 1H), 4.68 (d, J = 6.0
Hz, 2H), 4.48 (s, 2H); 13C NMR (150 MHz, CDCl3): δ 170.3,
151.1, 150.2, 144.7, 140.8, 133.1, 131.8, 131.7, 129.9, 129.5,
129.3, 128.6, 128.3, 126.9, 126.8, 126.7, 125.9, 124.9, 121.7,
119.1, 66.2, 43.7; IR (KBr)νmax 3071, 2958, 2930, 2857, 1739,
1584, 1552, 1523, 1482, 1455, 1423, 1365, 1326, 1259, 1155,
1071, 1015 cm-1; HRMS (ESI) Calcd For C22H18NO2S 360.1053
(M + H+); Found 360.1052.
A. H. Clark, J. D. McCorvy, J. M. Conley, W. K. Williams, M.
Bekkam, V. J. Watts and D. E. Nichols, Bioorg. Med. Chem.,
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C. N. Carrigan, S. A. Patel, H. D. Cox, E. S. Bolstad, J. M.
Gerdes, W. E. Smith, R. J. Bridges and C. M. Thompson,
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J. G. Cannon, K. A. Walker, A. Montanari, J. P. Long and J. R.
Flynn, J. Med. Chem., 1990, 33, 2000.
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Ethyl
2-(3-(4-methoxyphenyl)-2-methylbenzo[f]quinolin-1-
9
A. D. Abell, K. F. Erhard, H. K. Yen, D. S. Yamashita, M.
Brandt, H. Mohammed, M. A. Levy and D. A. Holt, Bioorg.
1
yl)acetate (12): Yield 72%, white solid, mp 76-77 ˚C, H NMR
(400 MHz, CDCl3): δ 8.37 (d, J = 6.8 Hz, 1H), 7.94 (d, J = 8.8 Hz,
2H), 7.88 (d, J = 8.8 Hz, 1H), 7.63-7.62 (m, 3H), 7.58 (s, 1H),
7.03 (d, J = 8.4 Hz, 2H), 4.42 (s, 2H), 4.38 (q, J = 7.6 Hz, 2H),
3.89 (s, 3H), 2.47 (s, 3H), 1.38 (t, J = 7.6 Hz, 3H); 13C NMR (100
MHz, CDCl3): δ 171.2, 159.9, 158.9, 147.1, 139.4, 133.9, 133.4,
130.9, 130.4, 129.8, 129.6, 129.2, 129.1, 128.9, 127.2, 126.9,
126.3, 125.0, 122.1, 114.0, 61.7, 55.6, 40.1, 17.7, 14.6; IR
(KBr)νmax 3055, 2957, 2932, 2836, 1738, 1607, 1577, 1516,
1549, 1510, 1477, 1451, 1427, 1368, 1301, 1178, 1109, 1019
cm-1; HRMS (ESI) Calcd For C25H24NO3 386.1751 (M + H+);
Found 386.1753.
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RSB acknowledge CSIR, New Delhi for Research Associate
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We thank the director of IIT Guwahati for creating general
laboratory facilities. We acknowledge gratefully for financial
support (grant no.: 02(0181)/14/EMR-II) from Council of
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Graphical Abstract
One-pot three component regioselective synthesis of C1-functionalised
3-arylbenzo[f]quinoline
Radhakrishna Gattu, R. Sidick Basha, Prasanta Ray Bagdi and Abu T. Khan*