Synthesis of New 3-Aryl-1-methylbenzo[f]quinolines

Article abstract of DOI:10.1023/A:1026077716902

Three-component condensation of 2-aminonaphthalene, acetone, and substituted benzaldehydes in alcoholic solution in the presence of concentrated hydrochloric acid gave 3-aryl-1-methylbenzo[f]quinolines. 1-Methyl-3- (nitrophenyl)benzo[f]quinolines were reduced to the corresponding amines which were converted into amides having a sulfonyl or chloroacetyl group in the aryl substituent.

Full text of DOI:10.1023/A:1026077716902

Russian Journal of Organic Chemistry, Vol. 39, No. 5, 2003, pp. 718 722. Translated from Zhurnal Organicheskoi Khimii, Vol. 39, No. 5, 2003,
pp. 765 769.
Original Russian Text Copyright
2003 by Kozlov, Basalaeva.
Synthesis of New 3-Aryl-1-methylbenzo[f]quinolines
N. G. Kozlov and L. I. Basalaeva
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
ul. Surganova 13, Minsk, 220072 Belarus
Received July 1, 2002
Abstract Three-component condensation of 2-aminonaphthalene, acetone, and substituted benzaldehydes in
alcoholic solution in the presence of concentrated hydrochloric acid gave 3-aryl-1-methylbenzo[f]quinolines.
1-Methyl-3-(nitrophenyl)benzo[f]quinolines were reduced to the corresponding amines which were converted
into amides having a sulfonyl or chloroacetyl group in the aryl substituent.
Synthesis of compounds of the benzoquinoline
series has been well documented [1 4]. They are
formed as final products of heterocyclization of Schiff
bases with various CH acids. Owing to their very poor
solubility in most organic solvents, benzoquinoline
derivatives are low reactive, and they cannot be used
in the synthesis of more complex molecules. Among
these compounds, methyl-substituted benzoquinolines
occupy a specific place: they are starting materials
in the synthesis of difficultly accessible and hence
poorly studied styrylquinolines. Despite a limited
number of known styryl derivatives, they have found
application in photochemistry. The conjugated system
including the quinoline ring and styryl group gives
rise to photosensitizing properties, so that these com-
pounds may be used as components of light-sensitive
layer in photographic materials [5]. However, specific
interest in styryl derivatives of quinoline is explained
by antitumor [6] and immunoprotective properties [7]
of some compounds of this series.
The goal of the present work was to develop a pro-
cedure for the synthesis of methyl-substituted aryl-
benzo[f]quinolines with a view to extend the source
of raw materials for the preparation of new styryl-
quinoline derivatives. We previously succeeded in
obtaining 3-aryl-1-methylbenzo[f]quinolines in 35
55% yield by condensation of 2-arylmethyleneamino-
naphthalenes with acetone in the presence of amino-
naphthalene hydrochloride. In the present work we
synthesized such compounds by three-component
condensation of acetone (I), 2-aminonaphthalene (II),
and benzaldehyde (III) (or substituted benzaldehydes
IV XXV) on heating in boiling ethanol in the pres-
ence of concentrated hydrochloric acid (Scheme 1).
The reaction was selective; no intermediate arylamino
ketones (which are usually formed in reactions of
Schiff bases with ketones [9]) were isolated.
As previously [10, 11], the effect of substituent in
the aldehyde on the yield of the final product was
observed. Acceptor substituents in the para position
Scheme 1.
III, XXVI, R = H; IV, XXVII, R = 4-F; V, XXVIII, R = 4-Cl; VI, XXIX, R = 4-Br; VII, XXX, R = 4-NO2; VIII, XXXI,
R = 4-OH; IX, XXXII, R = 4-Me2N; X, XXXIII, R = 4-Et2N; XI, XXXIV, R = 4-Et; XII, XXXV, R = 4-MeO; XIII, XXXVI,
R = EtO; XIV, XXXVII, R = 4-PrO; XV, XXXVIII, R = 4-MeS; XVI, XXXIX, R = 3-HO; XVII, XL, R = 3-O2N; XVIII,
XLI, R = 3-PhO; XIX, XLII, R = 2-O2N; XX, XLIII, R = 2-Me; XXI, XLIV, R = 2,3-(MeO)2; XXII, XLV, R = 2,5-(MeO)2;
XXIII, XLVI, R = 3-EtO-4-HO; XXIV, XLVII, R = 3-MeO-4-PhCH2O; XXV, R = 2-HO-4-Et2N.
1070-4280/03/3905-0718$25.00 2003 MAIK Nauka/Interperiodica

SYNTHESIS OF NEW 3-ARYL-1-METHYLBENZO[f]QUINOLINES
719
Scheme 2.
XLVIII, 4-H2N; XLIX, 3-H2N; L, 2-H2N; LII, 4-PhSO2NH; LIII, 3-PhSO2NH; LIV, 2-PhSO2NH; LVI, 4-ClCH2CONH;
LVII, 3-ClCH2CONH; LVIII, 2-ClCH2CONH.
of the aromatic ring favor the reaction most strongly,
and the yield of 3-aryl-1-methylbenzo[f]quinolines
XXVII XXX reaches 55 74%; the yields of 3-aryl-
1-methylbenzo[f]quinolines from aldehydes having
electron-donor substituents are considerably lower.
Presumably, substituents in the ortho-position of
the aromatic ring in the aldehyde exert steric effect
on the heterocyclization process. The yield of o-nitro
derivative XLII is lower by 10% despite favorable
electronic effect of the nitro group. The steric effect
is more pronounced in the reaction with o-methyl-
benzaldehyde (XX). In this case, the yield of benzo-
quinoline XLIII decreases by 25%.
Aldehydes having two substituents require more
severe conditions for the condensation to occur. The
reactions with 4-benzyloxy-3-methoxybenzaldehyde
(XXIV) and 2,3-dimethoxybenzaldehyde (XXI) took
7 h in the presence of increased amount of hydro-
chloric acid, and the yield of products XLIV and
XLVII did not exceed 20%. In the reaction with
4-diethylamino-2-hydroxybenzaldehyde (XXV) no
heterocyclization occurred. In this case, both steric
and electronic factors are unfavorable.
Nitro-substituted compounds XXX, XL, and XLII
were converted into amides LII LVIII (Scheme 2).
We tried to reduce 1-methyl-3-(nitrophenyl)benzo[f]-
quinolines XXX, XL, and XLII in several ways:
with iron in hydrochloric and acetic acid, with zinc or
magnesium in acetic acid, and with sodium dithionite.
However, these reducing agents turned out to be low
efficient. Acceptable results were obtained using
tin(II) chloride in concentrated hydrochloric acid on
heating for 1 h. Phenylsulfonylamino derivatives LII
LIV were synthesized by condensation of 3-(amino-
phenyl)-1-methylbenzo[f]quinolines XLVIII L with
benzenesulfonyl chloride (LI) in pyridine at 90
100 C. Presumably, in this reaction pyridine acts not
only as solvent but also as catalyst; it reacts with
chloride LI to form pyridinium salt LIX [12]:
Amides LVI LVIII were prepared by reaction
of 3-(aminophenyl)-1-methylbenzo[f]quinolines
XLVIII L with chloroacetone (LV) in hexane in
the presence of boron trifluoride ether complex.
The structure of the products was confirmed by
the IR, NMR, UV, and mass spectra (GC MS). Their
melting points, yields, and analytical data are given
in Table 1. The IR spectra of compounds XXVI L,
LII LIV, and LVI LVIII contain a clearly defined
band in the region corresponding to out-of-plane
bending vibrations of aromatic C H bonds (840
1
820 cm ), which arises from the two adjacent C H
bonds at C5 and C6 of the quinoline ring [13]. The
1
bands at 695 690 and 770 760 cm correspond to
bending vibrations of C H bonds in the benzene ring.
Compound XXVII shows in the IR spectrum a strong
1
band at 1150 cm , which belongs to stretching vibra-
tions of the C F bond; compounds XXVIII and
LVI LVIII are characterized by C Cl absorption at
1
850 845 cm ; the C Br bond in XXIX gives rise
1
to absorption band at 569 cm . Strong bands in the
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 5 2003

720
KOZLOV, BASALAEVA
Table 1. Yields, melting points, and elemental analyses of 3-aryl-1-methylbenzo[f]quinolines XXVI XLVII and their
derivatives XLVIII L, LII LIV, and LVI LVIII
Found, %
Calculated
Compound
no.
Yield,
%
mp,
C
Formula
C
H
N (Hlg)
C
H
N (Hlg)
XXVI
XXVII
XXVIII
XXIX
XXX
XXXI
XXXII
XXXIII
XXXIV
XXXV
XXXVI
XXXVII
XXXVIII
XXXIX
XL
52
68
70
74
55
40
6
155 156a 89.20
130
5.59
5.21
4.87 (6.58)
4.63 (11.50)
4.01 (22.91)
8.94
C20H15N
C20H14FN
89.21
83.62
79.18
68.98
76.43
84.21
84.62
84.70
88.88
84.28
84.35
84.40
80.00
84.21
76.43
86.43
76.43
89.04
80.00
80.00
80.00
82.75
84.51
84.51
84.51
73.58
73.58
73.58
73.33
73.33
73.33
5.58
4.88
4.61
4.02
4.46
5.26
6.41
7.06
6.40
5.68
6.07
6.42
5.40
5.26
4.46
5.26
4.46
6.00
6.06
6.06
6.06
5.91
5.63
5.63
5.63
4.72
4.72
4.72
4.73
4.73
4.73
5.21
4.88 (6.62)
4.61 (11.66)
4.02 (22.98)
8.92
182
79.19
4.62
4.00
4.43
5.25
6.40
7.06
6.36
5.67
6.06
6.43
5.42
5.24
4.45
5.24
4.47
6.01
6.05
6.04
6.04
5.90
5.64
5.62
5.58
4.70
4.74
4.67
4.69
4.75
4.69
C20H14ClN
C20H14BrN
C20H14N2O2
C20H15NO
C22H20N2
177 178a 68.98
193 194a 76.44
243a
240
138
84.20
84.63
84.71
88.84
4.90
8.98
8.23
4.70
4.69
4.49
4.27
4.43
4.87
8.93
3.89
8.90
4.96
4.22
4.23
4.26
3.46
9.86
9.87
9.84
6.57
6.58
6.62
4.91
8.97
8.24
4.72
4.68
4.47
4.28
4.44
4.91
8.92
3.88
8.92
4.96
4.24
4.24
4.24
3.45
9.86
9.86
9.86
6.60
6.60
6.60
9
C24H24N2
C22H19N
29
44
40
38
42
18
26
25
45
28
20
18
17
15
54
52
50
47
49
50
42
37
30
263 264
124 125a 84.26
C21H17NO
C22H19NO
C23H21NO
C21H17NS
C20H15NO
C20H14N2O2
C26H19NO
C20H14N2O2
C21H17N
C22H20NO2
C22H20NO2
C22H20NO2
C28H24NO2
C20H16N2
205 206
338 339
199
84.35
84.38
80.01
84.20
76.41
86.43
76.41
89.03
80.01
80.02
79.97
82.73
84.50
84.47
84.49
73.54
73.56
73.59
73.38
73.29
73.35
217
186a
170
XLI
XLII
188
164
305
227
XLIII
XLIV
XLV
XLVI
XLVII
XLVIII
XLIX
L
LII
LIII
LIV
LVI
269 270
154
270
263
267
241
235
243
210
198
C20H16N2
C20H16N2
C26H20N2O2S
C26H20N2O2S
C26H20N2O2S
C22H17ClN2O
C22H17ClNO2
C22H17ClNO2
7.74 (9.70)
7.80 (9.74)
7.79 (9.74)
7.77 (9.72)
7.77 (9.72)
7.77 (9.72)
LVII
LVIII
218 219
a
The melting points correspond to those reported in [4].
1
region 2860 2840 cm arise from stretching vibra-
tions of C H bonds in the methoxy groups of com-
pounds XXXV, XLIV, XLV, and XLVII. The IR
spectra of XLVIII L are characterized by the pres-
ence of two N H stretching vibration bands at 3430
group. A strong carbonyl absorption band is observed
in the spectra of compounds LVI LVIII in the region
1
1650 1640 cm .
The mass spectra of benzoquinolines XXVI L and
their derivatives LII LIV and LVI LVIII indicate
that these compounds are unstable under electron
impact. The most abundant ion (100%) is [M 2]+;
also, [M 1]+ (40 46%), [M 2 CH3]+ (25 30%),
M+ (20 25%), [M R]+ (20 25%), and R+ (30 35%)
ion peaks are observed. Compounds LII LIV show
in the mass spectra peaks with m/z 268 (55 60%),
which correspond to the [M NHSO2Ph]+ ion.
1
3410 and 3550 3530 cm , N H bending vibration
bands at 1630 1625 cm , and C N stretching vibra-
tion bands at 1310 1300 cm , which correspond to
the primary amino group.
Compounds LII IV show in the IR spectra absorp-
tion bands at 1350 1340 and 1170 1160 cm due to
asymmetric and symmetric vibrations of the S O
1
1
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 5 2003

SYNTHESIS OF NEW 3-ARYL-1-METHYLBENZO[f]QUINOLINES
721
Table 2. 1H NMR spectra of 3-aryl-1-methylbenzo[f]quinolines XXVI XLVII and their derivatives XLVIII L, LII
LIV, and LVI LVIII (2 5% solutions in DMSO-d6)
Chemical shifts , ppm (J, Hz)
Compound
no.
Me, s
PhR
XXVI
XXVII
XXVIII
XXIX
XXX
3.10
3.20
3.20
3.20
3.25
3.15
3.10
7.20 7.45 m, 7.50 7.70 m, 7.90 8.10 m, 8.20 8.40 m, 8.50 8.70 m, 8.90 d (7.0)
7.30 7.50 m, 7.60 7.80 m, 8.00 8.20 m, 8.25 8.40, 8.70 d (7.6)
7.50 7.80 m, 7.90 8.10 m, 8.40 d (7.5), 8.90 d (7.0)
7.10 d (7.0), 7.30 d (7.8), 7.80 d (8.2), 8.10 8.30 m, 8.90 d (8.0)
7.40 7.60 m, 8.00 d (7.4), 8.10 8.20 m, 8.30 s, 8.40 d (7.6), 8.60 d (7.0) , 8.90 d (8.0)
6.90 d (8.2), 7.50 7.70 m , 7.90 d (7.2), 8.10 d (7.8), 8.90 d (8.0), 9.40 s (1H, OH)
3.18 s (6H, 2CH3), 6.80 d (7.9), 6.95 d (8.0), 7.00 d (8.4), 7.30 d (7.0), 7.40 7.50 m, 7.90
8.10 m, 8.90 d (7.6)
XXXI
XXXII
XXXIII
XXXIV
3.15
3.10
1.20 t (6H, 2CH2CH3), 2.50 q (4H, 2CH2CH3), 6.80 d (7.0), 7.60 7.80 m, 7.90 8.20 m,
8.90 d (7.0)
1.20 t (3H, CH2CH3), 2.60 q (2H, CH2CH3), 7.20 7.40 m, 7.60 7.70 m, 7.80 8.20 m,
8.90 d (7.0)
XXXV
XXXVI
3.32
3.25
3.90 s (3H, OCH3), 7.20 d (8.0), 7.82 q, 8.16 d (7.3), 8.20 d (7.5), 8.30 8.36 m, 9.00 d (7.0)
1.50 t (3H, OCH2CH3), 4.70 q (2H, OCH2CH3), 6.70 6.90 m, 7.10 d (7.0), 7.80 8.10 m,
8.90 d (7.0)
XXXVII
3.15
0.80 t (3H, OCH2CH2CH3), 1.50 q (2H, OCH2CH2CH3), 3.50 t (2H, OCH2CH2CH3), 6.60
6.90 m, 7.00 d (7.0), 7.90 8.10 m, 8.95 d (7.0)
XXXVIII
XXXIX
XL
XLI
XLII
3.20
3.18
3.25
3.20
3.30
3.30
3.10
2.00 s (3H, SCH3), 7.10 d (8.0), 7.80 q, 8.20 d (7.0), 8.30 8.45 m, 9.00 d (7.0)
6.70 d (7.3), 6.90 d (7.5), 7.40 t, 7.60 7.80 m, 8.00 8.20 m, 8.90 d (7.0), 9.70 s (1H, OH)
7.60 7.70 m, 7.75 t, 7.87 8.02 m, 8.10 s, 8.26 d (7.0), 8.65 d (7.0), 8.82 d (7.0), 9.2 s
7.00 7.20 m, 7.30 7.60 m, 7.70 7.90 m, 8.00 8.20 m, 8.90 d (7.2)
7.30 7.50 m, 8.00 d (7.0), 8.20 8.40 m, 8.60 d (7.0), 8.90 d (8.0)
2.90 s (3H, OCH3), 7.70 d (7.2), 7.75 7.90 m, 8.00 q, 8.94 d (7.0)
3.90 s (3H, OCH3), 4.10 s (3H, OCH3), 7.10 7.20 m, 7.40 7.50 m, 7.60 7.80 m, 7.90 8.10 m,
8.80 d (7.1)
XLIII
XLIV
XLV
3.40
3.40
3.19
3.90 s (3H, OCH3), 4.03 s (3H, OCH3), 7.05 q, 7.60 d (7.4), 7.80 t, 8.10 d (7.0), 8.20 d (6.5),
8.90 d (7.0), 9.60 d (8.0)
1.49 t (3H, OCH2CH3), 4.30 q (2H, OCH2CH3), 7.00 d (7.0), 7.70 7.90 m, 8.00 s, 8.10 d
(7.2), 8.30 d (7.0), 8.60 d (7.8), 8.90 d (7.6)
3.90 s (3H, OCH3), 5.20 s (2H, OCH2), 6.80 7.20, 7.30 7.60 m, 7.80 7.90 m, 8.00 8.20 m,
8.80 d (7.0)
XLVI
XLVII
XLVIII
XLIX
L
LII
LIII
LIV
LVI
LVII
LVIII
3.15
3.15
3.10
3.30
3.30
3.35
3.30
3.25
3.20
5.50 s (2H, NH2), 6.70 d (8.3), 7.60 7.80 m, 7.90 8.20 m, 8.80 d (8.2)
5.45 s (2H, NH2), 6.60 d (8.0), 7.50 7.80 m, 8.00 8.20 m, 8.60 d (8.0)
5.50 s (2H, NH2), 6.70 d (8.0), 7.40 7.60 m, 7.80 8.00 m, 8.50 d (8.0)
6.50 d (8.0), 7.00 s, 7.50 7.70 m, 7.90 8.10 m, 8.20 8.40 m, 8.70 d (7.8)
6.60 d (8.0), 7.10 s, 7.40 7.60 m, 7.80 8.00 m, 8.30 8.50 m, 8.60 d (7.6)
6.60 d (8.0), 7.00 s, 7.50 7.70 m, 7.90 8.20 m, 8.30 8.50 m, 8.80 d (7.5)
4.25 d (2H, CH2Cl), 6.40 d (7.8), 7.10 7.30 m, 7.80 8.10 m, 8.30 8.45 m, 8.60 d (7.5)
4.20 d (2H, CH2Cl), 6.30 d (7.6), 7.00 7.30 m, 7.80 8.10 m, 8.30 8.40 m, 8.70 d (7.6)
4.20 d (2H, CH2Cl), 6.35 d (7.6), 7.10 7.40 m, 7.90 8.30 m, 8.40 8.60 m, 8.80 d (7.5)
The electron absorption spectra of compounds
XXVI L, LII LIV, and LIV LVIII appear in the
ultraviolet region, and the positions of absorption
maxima therein are similar to those in the spectra of
naphthalene compounds [14]. The absorption curve
has two long-wave absorption maxima which are
displaced to longer wavelength relative to the corre-
sponding bands of benzo[f]quinoline. Obviously,
this is the result of extension of the conjugated bond
system due to addition of the aryl fragment. Introduc-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 5 2003

722
KOZLOV, BASALAEVA
tion of donor substituents into the para position of
the benzene ring (compounds XXXI XXXVII) leads
to a red shift of the absorption maximum. Acceptor
substituents in the para position of the benzene ring
(compounds XXVII XXX) induce a blue shift of the
absorption maximum [15].
Table 2 contains the H NMR spectral parameters
of compounds XXVI XLVII, LII LIV, and LVI
LVIII. All these characteristically show a singlet at
3.10 3.40 ppm from the methyl group on C1 and
a doublet at 8.80 9.10 from 5-H. These data support
the structure of 3-aryl-1-methylbenzo[f]quinolines,
specifically the position of the methyl group on the
C1 atom [16].
poured into 50 ml of water. The oily product separat-
ed and solidified on cooling. It was filtered off and
recrystallized thrice from alcohol toluene (1:3).
3-(Chloroacetylaminophenyl)-1-methylbenzo[f]-
quinolines LVI LVIII. Boron trifluoride ether com-
plex, 5 ml, and chloroacetone (LV), 4.6 g (0.05 mol),
were added to a solution of 1 g (0.03 mol) of
3-(aminophenyl)-1-methylbenzo[f]quinoline XLVIII
L in 20 ml of dioxane, and the mixture was heated
for 30 40 min on a boiling water bath. The solvent
was distilled off, and the crystals were treated with
aqueous ammonia and recrystallized from alcohol
toluene (1:3).
1
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The IR spectra were recorded on a Protege-460
(Nicolet) spectrometer. The H NMR spectra were
1
2. Kozlov, N.S., Serzhanina, V.A., and Shmanai, G.S.,
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BS-567A (100 MHz) spectrometers. The chemical
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MAT Incos 50 instrument (electron impact, 70 eV).
The UV spectra were measured on a Specord UV-Vis
spectrophotometer in ethanol (c = 1 10 4 M).
3-Aryl-1-methylbenzo[f]quinolines XXVI
XLVII. A solution of 0.58 g (0.01 mol) of acetone
(I), 0.01 mol of benzaldehyde III XXV, 1.43 g
(0.01 mol) of 2-aminonaphthalene (II), and 3 7 drops
of concentrated hydrochloric acid in 20 30 ml of
ethanol was refluxed for 1 7 h. The mixture was
cooled, and the precipitate was filtered off, treated
with aqueous ammonia (for neutralization), and re-
crystallized from ethanol benzene (2:1).
3-(Aminophenyl)-1-methylbenzo[f]quinolines
XLVIII L. A solution of 3 g (0.015 mol) of SnCl2
in 3 ml of concentrated hydrochloric acid was added
to a mixture of 1 g (0.03 mol) of 1-methyl-3-(nitro-
phenyl)benzo[f]quinoline XXX, XL, or XLII and
10 ml of isopropyl alcohol. The mixture was heated
for 1 h on a water bath, cooled, and treated with
a 40% solution of sodium hydroxide with addition
of ice. The product was filtered off, washed with
water until neutral washings, and recrystallized from
toluene.
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[f]quinolines LII LIV. Benzenesulfonyl chloride
(LI), 0.5 g (0.003 mol), was added to a solution of
1 g (0.003 mol) of 3-(aminophenyl)-1-methylbenzo-
[f]quinoline XLVIII L in 5 ml of freshly distilled
pyridine, and the mixture was heated for 2 h on
a boiling water bath. The mixture was cooled and
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