Synthesis of benzo[f]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene

Article abstract of DOI:10.1007/s11176-005-0094-4

N-Arylmethylene-2-naphthylamines react with acetylcyclohexane and 1-acetylcyclohexene under mild conditions to afford 2-aryl-2-(2-naphthylamino) ethyl cyclohexyl and 1-cyclohexenyl ketones, respectively. Under more severe conditions (110°C), the reaction

Full text of DOI:10.1007/s11176-005-0094-4

Russian Journal of General Chemistry, Vol. 74, No. 11, 2004, pp. 1748 1753. Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 11, 2004,
pp. 1878 1883.
Original Russian Text Copyright
2004 by Grachek.
Synthesis of Benzo[f]quinoline Derivatives by Condensation
of N-Arylmethylene-2-naphthylamines with Acetylcyclohexane
and 1-Acetylcyclohexene
V. I. Grachek
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus
Received November 18, 2002
Abstract N-Arylmethylene-2-naphthylamines react with acetylcyclohexane and 1-acetylcyclohexene under
mild conditions to afford 2-aryl-2-(2-naphthylamino)ethyl cyclohexyl and 1-cyclohexenyl ketones, respec-
tively. Under more severe conditions (110 C), the reaction is accompanied by cyclization with formation of
3-aryl-1-cyclohexyl(or 1-cyclohexenyl)benzo[f ]quinolines. Proper choice of the amount of catalyst, tempera-
ture, and reaction time allows isolation of intermediate 3-aryl-1-cyclohexyl(or 1-cyclohexenyl)-3,4-dihydro-
benzo[f ]quinolines.
Quinoline derivatives are structural analogs of al-
kaloids [1], enzyme inhibitors [2], and antibiotics [3];
therefore, they should exhibit versatile biological
activity. In addition, these compounds are good anti-
oxidants [4] and antirads [5] for polymeric materials.
Interest in quinoline derivatives and analogs con-
tinuously increases. Some benzoquinolines were
found to possess good complexing [6] and fluorescent
properties [7].
and carbon atoms. Therefore, such cations readily take
up even weakly nucleophilic ketones. The reaction
mechanism is analogous to the acid-catalyzed aldol
addition pattern. The reaction involves the methyl
group in methyl ketone, so that the latter acts as CH
acid. Amino ketones IVa IVf and Va Vg thus
formed are the first intermediate products in the syn-
thesis of benzo[f]quinolines (see scheme). The double
bond in 1-acetylcyclohexene is conjugated with the
carbonyl group; as a result, polarization of the C=O
bond increases, and protons in the acetyl group be-
come more labile. Therefore, the yields of amino
ketones from 1-acetylcyclohexene are greater, and the
condensation occurs at a lower temperature, as com-
pared to acetylcyclohexane (Table 1). Amino ketones
IVa IVf and Va Vg were obtained by heating the
reactants in ethanol at 40 60 C in the presence of a
catalytic amount of hydrochloric acid.
A known procedure for the synthesis of benzo[f]-
quinolines is based on the condensation of Schiff
bases derived from 2-naphthylamine with various
aliphatic, aromatic, and heterocyclic methyl ketones
[8 12]. It was found that the formation of benzo[f]-
quinolines is a multistep process [12]. The reaction of
N-arylmethylene-2-naphthylamines with methyl ke-
tones of the cycloaliphatic series has been studied
poorly. We previously synthesized benzo[f]quinoline
derivatives by condensation of N-arylmethylene-2-
naphthylamines with acetylcyclohexane and 1-acetyl-
cyclohexene [13, 14]. In doing so, either no inter-
mediate products were isolated at all or they were
isolated in very small amounts. In the present work
we performed condensations of acetylcyclohexane (I)
and 1-acetylcyclohexene (II) with Schiff bases IIIa
IIIh of the 2-naphthylamine series using larger
amounts of the initial reactants and tried to isolate and
examine intermediate products by varying the reaction
conditions.
When the condensation was carried out under more
severe conditions, i.e., by heating equimolar amounts
of the reactants in toluene at 110 C in the presence of
hydrochloric acid as catalyst, the products were the
corresponding benzo[f]quinolines VIa VIh and
VIIa VIIh. The cyclization was accompanied by
formation of tarry products. Benzo[f]quinolines VI
and VII can also be obtained from amino ketones IV
and V under the same conditions; in this case, tarring
occurred to a lesser extent. The cyclization of amino
ketones IV and V to benzo[f]quinoline derivatives VI
and VII involves electrophilic attack by the carbonyl
carbon atom on the naphthalene -carbon atom,
followed by dehydration and dehydrogenation. It
should be noted that the condensation of Schiff bases
Condensations of Schiff bases with ketones are
catalyzed by acids. Proton addition to a Schiff base
yields the corresponding cation in which the positive
charge is delocalized over the azomethine nitrogen
1070-3632/04/7411-1748 2004 MAIK Nauka/Interperiodica

SYNTHESIS OF BENZO[f ]QUINOLINE DERIVATIVES BY CONDENSATION
1749
R
O
R
R
H
N
N
R
CH3
+
O
I, II
IIIa IIIh
IVa IVf, Va Vg
R
R
5
6
4
2
R
1
3
R
3
2
N4
10
7
NH
9
8
5
6
VIa VIh, VIIa VIIh
VIIIb, VIIIc, VIIIe, VIIIf, IXc, IXe, IXf
I, IV, VI, VIII, R = cyclohexyl; II, V, VII, IX, R = 1-cyclohexenyl; III IX, R = H (a), 4-F (b), 4-Cl (c), 4-Br (d),
4-NO2 (e), 3-NO2 (f), 4-OH (g), 4-NH2 (h).
with acetophenone requires milder conditions (heating
on a water bath for 10 15 min) and is not accom-
panied by tarring. Presumably, the cyclohexane and
cyclohexene rings in methyl ketones I and II create
stronger steric hindrances to cyclization, as compared
to the benzene ring in acetophenone.
strong absorption bands in the spectra of VIII and IX
originates from out-of-plane bending vibrations of the
1
aromatic C H bonds. The region 1500 900 cm
contains a number of closely located bands due to
vibrations of aromatic C H bonds and stretching
vibrations of the C N bond. In the IR spectra of
benzo[f]quinolines VI and VII we observed no ab-
By varying the reaction conditions in the condensa-
tion of ketones I and II with N-arylmethylene-2-
naphthylamines, namely the amount of the catalyst,
temperature, and reaction time, we succeeded in
isolating dihydro derivatives VIIIb, VIIIc, VIIIe,
VIIIf, IXc, IXe, and IXf which are also intermediate
products in the synthesis of benzo[f]quinolines VI and
VII. Compounds VIII and IX were obtained by
heating a mixture of the corresponding Schiff base
and ketone in boiling ethanol over a period of 3 6 h
or amino ketone over a period of 2 3 h.
1
sorption bands at 1680 and 3400 cm , which are
typical of C=O and N H bonds, respectively. In the
region corresponding to C=C stretching vibrations,
1
strong triplet bands at 1580 1550 cm and a strong
1
band at 1490 1480 cm were present. Absorption
1
bands at 2880 2830 cm belong to stretching vibra-
tions of aliphatic C H bonds in the cyclohexane
1
(cyclohexene) rings. A weak band at 1630 cm in the
spectra of VIIa VIIh was assigned to vibrations of
the C=C bond in the cyclohexene ring.
The IR spectra of amino ketones IVa IVf and
Va Vg contain absorption bands in the region 1680
The UV spectra of amino ketones IV and V
(Table 2) consist of three bands and resemble the
spectrum of 2-naphthylamine [ max, nm (log ): 246
(4.38), 280 (3.66), 342 (3.28)]. Taking into account
the above similarity and high absorption intensity, all
1
1660 cm due to carbonyl stretching vibrations;
1
absorption in the region 3400 3390 cm corresponds
to stretching vibrations of the N H group; stretching
vibrations of the aromatic C H bonds give rise to
these bands may be attributed to
the benzene rings. Weak bands due to n
tion involving lone electron pair on the nitrogen atom
are overlapped by the strong *-transition bands.
* transitions in
1
absorption bands at 3090 3000 cm ; and strong
* transi-
absorption bands from aromatic C=C bonds appear at
1
1630 1500 cm . The IR spectra of dihydro deriva-
tives VIIIb, VIIIc, VIIIe, VIIIf, IXc, IXe, and
IXf lack absorption in the region 1680 1660 cm , in
keeping with their cyclic structure. A set of very
Substituents in the benzene ring almost do not affect
the shape of the spectral curve: only a slight shift of
the absorption maxima is observed. The UV spectra
1
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 11 2004

1750
GRACHEK
Table 1. Yields, melting points, and elemental analyses of compounds IV IX
Found, %
Calculated, %
H
Comp. no. Yield, % mp,
C
Formula
C
H
N
C
N
IVa
IVb
IVc
IVd
IVe
IVf
Va
Vb
Vc
Vd
Ve
Vf
Vg
VIa
VIb
VIc
VId
VIe
VIf
VIg
VIh
VIIa
VIIb
VIIc
VIId
VIIe
VIIf
VIIg
VIIh
VIIIb
VIIIc
VIIId
VIIIe
IXc
IXe
IXf
67
59
60
58
49
43
72
65
67
63
60
49
61
72
68
64
54
49
46
60
63
64
59
61
63
38
42
60
63
28
22
36
33
29
23
25
165 166
176 177
181 182
187 188
170 171
175 176
164 165
173 174
182 183
192 193
168 169
171 172
162 163
140 141
166 167
169 170
181 182
174 175
172 173
169 170
175 176
138 139
169 170
173 174
182 183
178 179
175 176
168 169
172 173
217 218
211 212
215 216
203 204
210 211
218 219
205 206
84.02
79.98
76.51
68.80
74.70
74.58
84.60
80.50
77.08
69.11
74.99
74.97
80.82
88.94
84.54
80.80
72.11
78.57
78.57
84.92
85.14
89.63
84.93
81.15
72.51
78.89
78.87
85.51
85.74
84.08
80.29
78.17
78.14
80.80
78.47
78.58
7.48
7.00
6.89
6.04
6.58
6.52
7.02
6.50
6.18
5,63
6.21
6.07
6.75
6.90
6.18
5.95
5.27
5.83
5.74
6.59
6.91
6.29
5.70
5.45
4.85
5.33
5.28
6.06
6.32
6.78
6.45
6.31
6.31
5.99
5.86
5.84
4.08
3.72
3.50
3.16
6.91
6.99
3.97
3.71
3.62
3.25
7.05
6.98
3.72
4.02
3.99
3.79
3.92
7.38
7.38
3.99
7.97
4.05
4.01
3.83
3.32
7.36
7.39
3.98
8.02
3.89
3.80
7.30
7.33
3.75
7.28
7.27
C25H27NO2
C25H26FNO
C25H26ClNO
C25H26BrNO
C25H26N2O3
C25H26N2O3
C25H25NO
C25H24FNO
C25H24ClNO
C25H24BrNO
C25H24N2O3
C25H24N2O3
C25H25NO2
C25H23N
84.00
80.01
76.50
68.79
74.61
74.61
84.52
80.44
77.00
69.13
75.01
75.01
80.87
88.98
84.52
80.73
72.10
78.51
78.51
84.96
85.10
89.55
84.99
81.17
72.47
78.93
78.93
85.48
85.72
84.04
80.33
78.10
78.10
80.77
78.52
78.52
7.60
6.93
6.68
5.99
6.50
6.50
7.04
6.43
6.19
5.56
5.99
5.99
6.73
6.86
6.20
5.96
5.32
5.79
5.79
6.66
6.86
6.27
5.66
5.44
4.86
5.29
5.29
5.98
6.28
6.72
6.42
6.29
6.29
5.92
5.79
5.79
3.91
3.73
3.58
3.21
6.96
6.96
3.94
3.75
3.59
3.22
7.00
7.00
3.77
4.10
3.94
3.76
3.96
7.32
7.32
3.96
7.95
4.18
3.96
3.79
3.38
7.36
7.36
3.99
8.00
3.92
3.75
7.29
7.29
3.77
7.32
7.32
C25H22FN
C25H22ClN
C25H22BrN
C25H22N2O2
C25H22N2O2
C25H23NO
C25H24N2
C25H21N
C25H20FN
C25H20ClN
C25H20BrN
C25H20N2O2
C25H20N2O2
C25H21NO
C25H22N2
C25H24FN
C25H24ClN
C25H24N2O2
C25H24N2O2
C25H22ClN
C25H22N2O2
C25H22N2O2
of dihydro derivatives VIII and IX are also charac-
terized by the presence of three strong absorption
VII contain bands typical of isoelectronic phenan-
threne [16]. Replacement of the CH group in phenan-
threne by nitrogen atom leads to increase in the
intensity and red shift of the absorption maxima due
to inductive effect of the nitrogen atom and reduction
in the molecular symmetry. The absorption curves of
benzo[f]quinoline derivatives VI and VII are systems
bands belonging to
*-electronic transitions in the
naphthalene core, but their maxima are appreciably
displaced to longer wavelength relative to the cor-
responding maxima of amino ketones IV and V.
Presumably, the
* transitions in molecules VIII
and IX are contributed by lone electron pair on the
nitrogen atom [15]. Substituents in the benzene ring
weakly affect the position of the main absorption
bands. The UV spectra of benzo[f]quinolines VI and
including three bands:
,
p, and
;
the
-band is the most intense, and the -band is charac-
terized by a distinct vibronic structure. The absorp-
tion maxima in the UV spectra of cyclohexenyl-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 11 2004

SYNTHESIS OF BENZO[f ]QUINOLINE DERIVATIVES BY CONDENSATION
1751
Table 2. UV spectra of compounds IVa IVd, Va, Vc Vf, VIa, VIc VIf, VIIa, VIIc VIIf, VIIIb, VIIIc, IXc, and IXd
Comp. no.
max, nm (log )
Comp. no.
max, nm (log )
IVa
IVb
IVc
IVd
Va
Vc
Vd
Ve
Vf
242 (4.53), 280 (3.87), 344 (3.46)
244 (4.41), 282 (3.94), 346 (3.31)
243 (4.62), 282 (3.96), 346 (3.43)
244 (4.59), 284 (3.66), 345 (3.38)
243 (4.61), 284 (3.97), 348 (3.42)
240 (4.65), 284 (3.89), 349 (3.40)
247 (4.58), 286 (3.92), 350 (3.39)
248 (4.70), 288 (3.79), 352 (3.34)
246 (4.65), 283 (3.85), 347 (3.38)
278 (4.63), 330 (3.65), 359 (3.61)
280 (4.62), 334 (3.59), 360 (3.67)
281 (4.42), 334 (3.63), 361 (3.60)
VIe
VIf
285 (4.58), 336 (3.79), 367 (3.64)
280 (4.46), 332 (3.53), 360 (3.59)
281 (4.70), 336 (3.70), 362 (3.72)
282 (4.62), 346 (3.61), 364 (3.64)
283 (4.57), 348 (3.62), 365 (3.58)
292 (4.48), 345 (4.26), 370 (4.03)
284 (4.60), 347 (3.86), 363 (3.78)
258 (4.68), 309 (3.78), 373 (3.48)
259 (4.63), 308 (3.69), 376 (3.52)
266 (4.67), 316 (3.79), 380 (3.60)
268 (4.62), 318 (3.61), 372 (3.58)
VIIa
VIIc
VIId
VIIe
VIIf
VIIIb
VIIIc
IXc
VIa
VIc
VId
IXd
Table 3. 1H NMR spectra of benzo[f ]quinoline derivatives VIa VIf and VIIa VIIh, , ppm (J, Hz)
Benzoquinoline system
H5 7, m
H8,9, d
R C6H4
H2 , H3 ,
R
Comp.
no.
2H3 ,
2H4 ,
H1 ,
H2, s
H10, d
H2 , s
H6 , m H5 , s
2H6 , s 2H5 , s 10H2
, m
6
VIa
VIb
VIc
VId
VIe
VIf
VIIa
VIIb
VIIc
VIId
VIIe
VIIf
VIIg
VIIh
7.54
7.45
7.46
7.46
7.47
7.46
7.56
7.49
7.48
7.48
7.46
7.48
7.48
7.46
7.86 7.92 7.60 (3J 9.2) 9.12 (3J 7.4) 7.98
7.79 7.82 7.58 (3J 9.0) 9.10 (3J 7.4) 7.95
7.40
7.36
7.32
7.36
7.92
7.30
7.30
7.22
7.20
7.37
7.96
7.28
7.24
7.88
1.18
1.20
1.21
1.22
1.20
1.18
7.78 7.81 7.57 (3J 9.2) 9.10
7.96
7.78 7.81 7.57 (3J 9.2) 9.10 (3J 7.4) 7.94
7.80 7.84 7.59 (3J 9.2) 9.14 (3J 7.3) 7.92
7.81 7.85 7.58 (3J 9.0) 9.10 (3J 7.3) 7.94
7.88 7.92 7.60 (3J 9.2) 9.18 (3J 7.2) 7.98
7.79 7.84 7.58 (3J 9.0) 9.00 (3J 7.2) 8.00
7.78 7.82 7.58 (3J 9.0) 9.00 (3J 7.3) 8.00
7.79 7.83 7.58 (3J 9.2) 9.00 (3J 7.3) 7.94
7.80 7.83 7.64 (3J 9.2) 9.14 (3J 7.2) 7.96
7.80 7.84 7.60 (3J 9.2) 9.02 (3J 7.3) 7.93
7.78 7.82 7.57 (3J 9.2) 9.12 (3J 7.3) 7.98
7.76 7.81 7.60 (3J 9.0) 9.12 (3J 7.2) 7.94
5.86
5.80
5.80
5.80
5.72
5.75
5.84
5.82
2.03
2.04
2.04
2.00
2.06
2.02
2.06
2.04
1.58
1.56
1.60
1.60
1.58
1.54
1.56
1.59
substituted benzo[f]quinolines VIIa VIIh are dis-
placed to the red region, and their intensity is larger,
as compared to cyclohexane derivatives VIa VIh; this
is the result of conjugation between the cyclohexene
C=C bond and the other part of the molecule.
ring equivalent: they give a signal at 7.92 ppm in
the spectrum of VIe and at 7.96 ppm in spectrum of
VIIe. The signal at
1.18 1.21 ppm belongs to
protons in the cyclohexane ring, and signals from
methylene protons in the cyclohexene ring appear at
2.00 2.06 and 1.54 1.60 ppm. Unlike compounds
VI and VII, dihydro derivatives VIII and IX display
in the 1H NMR spectra signals at 4.81 and 6.22 ppm,
which belong to the NH and 3-H protons, respectively.
1
The H NMR spectra of benzo[f]quinolines VI and
VII (Table 3) contain a signal at 7.45 7.56 ppm,
which belongs to 2-H in the pyridine ring. Protons in
the phenyl ring give a multiplet at 7.92 7.98 ppm
and a signal at 7.20 7.40 ppm. Substituents in the
phenyl ring (except for the nitro group) weakly affect
the proton chemical shifts. The presence of a nitro
group in the para position makes protons in the phenyl
Benzo[f]quinoline derivatives are promising from
the viewpoint of stabilization of polymeric materials
against simultaneous action of temperature and radia-
tion. Intermediate -amino ketones of the naphthalene
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 11 2004

1752
GRACHEK
series attract interest as potential biologically active
substances and initial compounds for the synthesis of
various oxygen- and nitrogen-containing organic
compounds.
3-Aryl-1-cyclohexyl-3,4-dihydrobenzo[f]quino-
lines VIIIb, VIIIc, VIIIe, and VIIIf (general proce-
dure). A solution of 15 mmol of acetylcyclohexane
(I), 10 mmol of Schiff base IIIb, IIIc, IIIe, or IIIf,
and 0.15 ml of concentrated hydrochloric acid in
50 ml of ethanol was heated for 4 h under reflux. The
mixture was cooled, neutralized with aqueous
ammonia, and evaporated by 1/4 of the initial volume.
The precipitate was filtered off, washed with water
and ethanol, and recrystallized from ethanol nitro-
methane (1:1).
EXPERIMENTAL
1
The H NMR spectra were recorded on a Tesla BS-
567 spectrometer (100 MHz) from solutions in ben-
zene-d6 containing HMDS as internal reference. The
IR spectra were obtained on a UR-20 instrument from
samples prepared as KBr pellets. The UV spectra were
measured on a Specord UV-Vis spectrophotometer.
The melting points were determined on a Kofler
device. Acetylcyclohexane (I) was synthesized by the
procedure described in [13]. 1-Acetylcyclohexene (II)
was obtained from cyclohexene and acetyl chloride
according to [14].
3-Aryl-1-(1-cyclohexenyl)-3,4-dihydrobenzo[f]-
quinolines IXc, IXe, and IXf (general procedure).
1-Acetylcyclohexene (II), 12 mmol, was added to a
solution of 10 mmol of Schiff base IIIc, IIIe, or IIIf
and 0.13 ml of concentrated hydrochloric acid in
50 ml of ethanol. The mixture was heated for 2.5 h
under reflux and cooled, and the precipitate was
filtered off, treated with aqueous ammonia, washed
with ethanol, and recrystallized from ethanol nitro-
methane (1:1).
N-Arylmethylene-2-naphthylamines IIIa IIIh
were synthesized by heating equimolar amounts of the
corresponding aldehyde and 2-naphthylamine in
ethanol [17].
Cyclization of amino ketones IVa IVf and Va
Vg (general procedure). a. A solution of 5 mmol of
amino ketone IVa IVf or Va Vg and 0.20 0.25 ml of
concentrated hydrochloric acid in 25 ml of toluene
was heated for 2.5 3 h at 110 C. The precipitate of
benzo[f]quinoline VIa VIf or VIIa VIIg was filtered
off, treated with aqueous ammonia, and recrystallized.
Yield 56 72%.
2-Aryl-2-(2-naphthylamino)ethyl
cyclohexyl
ketones IVa IVf (general procedure). A solution of
10 mmol of Schiff base IIIa IIIf and 10 mmol of
acetylcyclohexane (I) in 40 ml of ethanol was heated
to 60 C, and 0.06 0.07 ml of concentrated hydro-
chloric acid was added. After cooling, crystals pre-
cipitated from the solution. The product was neutra-
lized with aqueous ammonia, filtered off, and purified
by repeated crystallization from ethanol.
b. A solution of 5 mmol of amino ketone IVb, IVc,
IVe, IVf, Vc, Ve, or Vf and 0.20 ml of concentrated
hydrochloric acid in 25 ml of ethanol was heated for
2 3 h under reflux. The products were isolated as
described above for the synthesis of dihydrobenzo[f]-
quinolines VIII and IX. Yield 29 40%.
2-Aryl-2-(2-naphthylamino)ethyl 1-cyclohexenyl
ketones Va Vg were synthesized in a similar way
using 1-acetylcyclohexene (II) and the corresponding
Schiff base IIIa IIIg on heating to 40 C.
Dehydrogenation of 3,4-dihydrobenzo[f]quino-
lines VIIIb, VIIIc, VIIIe, VIIIf, IXc, IXe, and IXf
(general procedure). A solution of 5 mmol of dihydro-
benzoquinoline VIIIb, VIIIc, VIIIe, VIIIf, IXc, IXe,
or IXf and 0.15 0.20 ml of concentrated hydrochloric
acid in 25 ml of ethanol was heated for 2 2.5 h under
reflux. The products were isolated as described above
for the synthesis of benzo[f]quinolines VI and VII.
Yield 56 74%.
3-Aryl-1-cyclohexylbenzo[f]quinolines VIa VIh.
A mixture of 10 mmol of acetylcyclohexane (I),
10 mmol of Schiff base IIIa IIIh, 0.3 0.35 ml of
concentrated hydrochloric acid, and 40 ml of toluene
was heated for 4 5 h at 110 C. After cooling, the
precipitate was filtered off, treated with aqueous
ammonia, washed with ethanol, and recrystallized
from ethanol toluene (3:1).
REFERENCES
3-Aryl-1-(1-cyclohexenyl)benzo[ f ]quinolines
VIIa VIIh were synthesized as described above for
compounds VIa VIh from methyl ketone II and
Schiff bases IIIa IIIh as initial compounds. After
cooling, the precipitate (somewhat contaminated with
tars) was filtered off, washed with ethanol, treated
with aqueous ammonia, and purified by repeated
crystallization from ethanol toluene (4:1).
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