Synthesis of 7-[4-alkoxy-3-methoxy(hydroxy)phenyl]-10,11-dihydro-benzo[c] acridin-8(7H,9H,12H)-ones and 4-(8-oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridin- 7-yl)-2-methoxy(ethoxy)phenyl esters of carboxylic acids

Article abstract of DOI:10.1134/S1070428010050234

Reactions of azomethines (Schiff bases) prepared from vanillin and vanillal ethers and 1-naphthylamine with cyclohexane-1,3-dione in butanol afforded in 40-64% yields 7-[4-alkoxy-3-methoxy(hydroxy)phenyl]-10,11-dihydrobenzo[c] acridin-8(7H,9H,12H)-ones an

Full text of DOI:10.1134/S1070428010050234

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2010, Vol. 46, No. 5, pp. 740−745. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © N.G. Kozlov, L.I. Basalaeva, B.A. Odnoburtsev, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 5,
pp. 751−757.
Synthesis
of 7-[4-Alkoxy-3-methoxy(hydroxy)phenyl]-10,11-dihydro-
benzo[c]acridin-8(7H,9H,12H)-ones
and 4-(8-Oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridin-7-yl)-
2-methoxy(ethoxy)phenyl Esters of Carboxylic Acids
N. G. Kozlov, L. I. Basalaeva, and B. A. Odnoburtsev
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
Minsk, 220072 Belarus
e-mail: loc@ifoch.bas-net.by
Received April 23, 2009
Abstract— Reactions of azomethines (Schiff bases) prepared from vanillin and vanillal ethers and 1-naphthylamine
with cyclohexane-1,3-dione in butanol afforded in 40–64% yields 7-[4-alkoxy-3-methoxy(hydroxy)phenyl]-10,11-
dihydrobenzo[c]acridin-8(7H,9H,12H)-ones and 4-(8-oxo-7,8,9,10,11,12-hexahydrobenzo[C]acridin-7-yl)-2-
methoxy(ethoxy)phenyl esters of carboxylic acids. The reaction products presumably formed by the rearrangement
of the azomethine adduct with the cyclohexane-1,3-dione proceeding by the type of Hofmann–Martius
rearrangement. The structure of compounds synthesized was confirmed by the elemental analysis, UV, IR, and 1H
NMR spectra.
DOI: 10.1134/S1070428010050234
The introduction of fragments of natural compounds,
like ethers of vegetable phenols, into molecules of
benzoacridines is a promising route to new biologically
active substances. In a series of publications [1–3] syn-
theses were described based on acridine derivatives giving
labeled conjugates with drugs, peptides, proteinc or nucleic
acids, of substances with an antitumor activity or DNA-
binding properties.An information reported in [4] showed
that the modified acridine molecules, in particular, the
tetrahydroderivatives possessing a carbonyl group
(alkaloid floxacrin analogs) exhibited higher antibacterial
action than the decarbonylated compounds of this series.
reactions of the condensation products of 1-naphthyl-
amine (I) and ethers IIa–IIh with cyclohexane-1,3-dione
(III). Azomethines IVa–IVh obtained from 3-alkoxy-4-
methoxy(hydroxy)benzaldehydes IIa–IIc and 4-formyl-
2-methoxy-(ethoxy)-phenyl esters of carboxylic acids
IId–IIh with 1-naphthylamine (I) were isolated as
individual E-isomers [6] in contrast to results published
in [7] stating that the synthesis of these compounds failed.
Our successful results made it possible to use the
compounds obtained in the reaction discussed below. This
reaction provided in 40–64% yield previously unknown
7-[4-alkoxy-3-methoxy(hydroxy)-phenyl]-10,11-
dihydrobenzo-[c]acridin-8(7H,9H,12H)-ones Va–Vc and
4-(8-oxo-7,8,9,10,11,12-hexahydro-benzo[c]acridin-7-yl)-
2-methoxy(ethoxy)phenyl esters Vd–Vh. The reaction
was performed by boiling the equimolar amounts of the
reagents in butanol. Owing to the high reactivity of the
β-dicarbonyl compound the process did not require acid
catalysts. The absence of acid favored the protection of
the labile ester group. The use in this reaction of the
Unlike the benzo[a]acridone derivatives obtained from
2-naphthylamine, the compounds of this class obtained
proceeding from 1-naphthylamine, benzo[c]acridones, are
less known. We formerly reported on the investigation of
reactions of Schiff bases obtained from vanillin or vanillal
ethers and 1-naphthylamine with dimedone (5,5-dimethyl-
cyclohexane-1,3-dione) [5]. In this study we explored the
740

SYNTHESIS OF7-[4-ALKOXY-3-METHOXY(HYDROXY)PHENYL]-...
741
previously reported data [7, 11, 12], applying the combined
analysis of all types of 2D NMR (COSY, NOESY, HSQC
and HMBC) and of the XRD data we established that
the only products of the reactions between compounds
IVa–IVh and cyclohexane-1,3-dione (III) regardless the
structure of the acid part of the ester group are 7-[4-
alkoxy-3-methoxy(hydroxy)-phenyl]-10,11-dihydro-
benzo[c]acridin-8-(7H,9H,12H)-ones or 4-(8-oxo-
7,8,9,10,11,12-hexahydrobenzo-[c]acridin-7-yl)-2-
methoxy(ethoxy)phenyl esters of carboxylic acids Va–
Vh. The structure of compounds synthesized is consistent
with the UV, IR, and 1H NMR spectra.
cyclic β-diketone provided a possibility to introduce a
carbonyl group into the structure of the fused heterocycle
simultaneously with the formation of the partially
hydrogenated benzo[h]quinoline fragment (see the
scheme).
Azomethine IVa–IVh in keeping with the reaction
mechanism that we assumed added a molecule of
cyclohexane-1,3-dione (III) forming intermediate A,
which further suffered protonation in reaction with the
solvent molecule (AlkOH) and converted into cation B.
Further the alkoxide anion formed in the previous stage
attacked cation B at the asymmetric carbon atom leading
to the hydramine cleavage of this structure into 1-naphthyl-
amine (I) and ether C. The latter reacted with 1-naph-
thylamine (I) adding either to the amino group or to the
carbon atom possessing the largest electron density and
situated in the β-position of the naphthalene framework.
Therewith formed respectively intermediate A or 2-{[3-
alkoxy-4-methoxy(hydroxy)phenyl](1-aminonaphth-2-
yl)methyl}-hexane-1,3-dione D. We believe that the latter
event is preferable since in the final stage formed
benzo[c]acridone derivatives Va–Vh that could be
obtained only by dehydrocyclization of intermediate D.
From the data reported in [7] it is presumable that the
water molecule liberated in the dehydrocyclization stage
takes part in the protonation of intermediate A as well as
the alcohol molecules.
The electron absorption spectra of esters Vd–Vh are
characterized by four maxima in the UV region: at 215–
227, 239–269, 279–286, and 368–378 nm. The complex
spectral pattern is due to the presence in the structure of
compounds synthesized of several chromophore frag-
ments: naphthalene framework, benzene rings, and also
a carbonyl and an ester groups.
It is known that in the case of incomplete association
of amines in the IR spectra alongside the absorption
bands of the associated amino groups apeear also the
bands of free group NH [13]. In compounds Va–Vh we
obtained the absorption band of the stretching vibtations
of the free secondary amino group appears in the region
3448–3425 cm–1, and of the associated group, at 3342–
3283 cm–1. It is also known that the stronger the
absorption band of the bound amino group is shifted to
lower frequencies and the higher its intensity, the more
molecules are associated [13]. Among the compounds
Va–Vh the most associated are Va–Vc, Vg, Vh, and
compounds Vd, Ve, Vf are virtually not associated. In
the IR spectra of the phenyl esters of the carboxylic acids
Vd–Vh the strong band νC=O is observed in the region
1767–1758 cm–1. The conjugation of the carbonyl group
with multiple bonds reduces the frequency of the νC=O
vibration for all types of carbonyl compounds by about
20 cm–1 [13]. Therefore in the IR spectrum of compound
Vh the strong vibration band of the ester carbonyl is shifted
to 1740 cm–1. The absorption band of the vinylog amide
fragment appears at 1602–1578 cm–1. The intensity of
this absorption is higher than that of the ester group
carbonyl absorption. These data are in agreement with
the results of [7, 14]. The very strong band in the region
1502–1490 cm–1 should be assigned to the skeleton
vibrations of aromatic carbon-carbon bonds. The
strongest bands in the region 1129–1013 cm–1 correspond
to the vibrations of the fragment C–O–C belonging to
ether and ester groups. Out-of-plane bending vibrations
of C–H bonds in the aromatic and heteroaromatic rings
The formation of compound D may be regarded as
resulting from the rearrangement of cation B by migration
of arylmethylenecyclohexanedione fragment into the
β-position of the naphthalene skeleton analogously to the
transformation of halides of alkyl-, dialkylanilines and
trialkylphenylammonium salts known under the name of
Hofmann–Martius rearrangement [8].
The mechanism described is analogous to that
suggested for the preparation of 7-(o- and p-R-phenyl)-
8,9,10,11-tetrahydrobenzo[c]acridin-8-ones [7] and cor-
responds to the mechanism of the synthesis of benzo-
[c]acridines from 2-(naphthylaminomethylene)cyclohexa-
nones [9].
A similar reaction of dimedone, 1-naphthylamine, and
some aromatic aldehydes in ethanol was investigated in
[10]. .Lielbriedis et al. believed that the reaction products
were hexahydrobenzo[c]phenanthridines, structures
isomeric to hexahydrobenzo[c]acridinones formed as
a result of the cyclocondensation of the reaction product
of dimedone and Schiff bases. However using in the
structure assignment of compounds all the spectral data
given further and taking into consideration all the
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 5 2010

KOZLOV et al.
742
Scheme.
O
O
NH2
N........H O
+
+
H
C
R3O
R1O
OR2
O
R4
O
I
R1O
III
O
OR2
IIa_IIc
IId_IIh
IVa_IVh
O
H
O
H
N
+
N
AlkOH
H
O
O
_
AlkO:
R1O
R1O
OR2
OR2
A
B
O H2N
O
..
H2N
H
O
O
OR2
AlkO
_AlkOH
OR1
R1O
C
OR2
D
_H2O
_H2O
8
8
12
HN
12
HN
O
O
1
4
3'
2'
OR3
1
4
OR1
2'
4'
1'
3'
2
3
7
2
3
7
1'
4'
6
6
OR2
O
5
5
O
R4
Vd_Vh
Va_Vc
R1 = H, R2 = Me (a); R1 = R2 = Me (b); R1 + R2 = OCH2O (c); R3 = R4 = Me (d); R3 = Me: R4 = Et (e), i-C3H7 (f), Ph (g);
R3 = Et, R4 = Me (h).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 5 2010

SYNTHESIS OF7-[4-ALKOXY-3-METHOXY(HYDROXY)PHENYL]-...
743
'
'
appear as a single band or a set of strong bands at 797–
694 cm–1.
spectrophotometer Nicolet Protege-460 frpm KBr pellets.
UV spectra were registered on a spectrophotometer
Specord UV Vis from (4–7) × 10–5 M solutions of
compounds in ethanol. 1H NMR spectra were registered
on spectrometers Bruker DRX-500 (500 MHz), Tesla
BS-567 (100 MHz), and Tesla BS-587 (80 MHz) from
5% solutions in DMSO-d6, internal reference TMS.
Melting points of the compounds were measured on the
Koeffler heating block.
In the 1H NMR spectra of benzo[c]acridone deriva-
tives Va–Vh the proton of the secondary amino group
gives rise to a singlet in the region 9.14–9.28 ppm. The
singlet at 4.94–5.30 ppm should be assigned to the methine
proton H7 of the dihydropyridine ring. The downfield shift
of this proton as compared to the common position of the
methine proton signals in cyclic compounds [15] is
caused by the anisotropic effect of the contiguous
aromatic rings. The protons of methylene groups linked
to C9, C10, and C11 give rise each to two broadened
doublets at 2.16–2.22 (2J 16.4–17.2 Hz), 2.30–2.40
(2J 16.2–16.9 Hz), and 2.80–2.90 ppm (2J 16.5–17.1 Hz)
respectively. The signal of proton H9 is located upfield
compared to the signals of protons H10 and H11 because
of the shielding effect of the adjacent carbonyl group. In
the region 2.15–2.30 ppm the signals of the methoxy-
carbonyl groups of the esters of the carboxylic acids
appear as singlets. The singlet of methoxy group protons
in compounds Va, Vb, Vd–Vg is observed in the region
3.70–3.78 ppm. The protons of the ethoxy group in the
ester Vh appear as a triplet at 1.35–1.39 ppm and
a broadened quartet at 3.83–3.88 ppm with a coupling
constant of 5.5–6.2 Hz. The protons of the naphthalene
framework are observed as two doublets and a multiplet.
The diffuse doublet at 8.40–8.48 ppm with the coupling
constant 7.0–7.8 Hz should be assigned to proton H1 in
agreement with the data of [16]. The multiplet in the region
7.16–7.67 ppm and a broadened doublet at 7.76–7.84
ppm with the coupling constant 7.8–8.4 Hz belongs to
the other five protons H2–6. The protons of H3', H5', and
H6’ of vanillin and vanillal framework appear as a singlet
and two doublets respectively (the singlet of proton H3'
in the region 6.90–7.15 ppm, and doublets of protons H6'
and H5', in the region 6.57–6.73 and 6.74–6.98 ppm with
a coupling constant 7.0–7.8 Hz). The slight upfield shift
of the signal of proton H3' in compound Vh compared
with the signal of this proton in compounds Va–Vg may
result from the stronger +M-effect of the ethoxy group
compared with the +M-effect of the methoxy group.
Besides the upfield shift of the signals of protons H3', H5',
and H6' may be due to the shielding effect of the bulky
substituent R’ [C9H19, CH2CH(Me)Ph]. The protons of
the phenyl substituent in the spectrum of benzoate IVg
appear as a multiplet in the region 7.25–8.15 ppm.
Azomethines IVa–IVh were synthesized by
procedure [9].
Compounds Va–Vc. A solution of 2 mmol of
cyclohexane-1,3-dione (III) and 2 mmol of azomethine
IVa–IVc in 30 ml of butanol was boiled for 3–10 h. The
separated precipitate was filtered off, washed with ether,
and recrystallized from ethanol. Yield of ethers Va–Vc:
50–57%.
7-(4-Hydroxy-3-methoxyphenyl)-10,11-
dihydrobenzo[c]acridin-8(7H,9H,12H)-one (Va).
Yield 50%, mp 241–243°C. IR spectrum, ν, cm–1: 3387,
3050, 3021, 2961, 2924, 2875, 1590, 1514, 1489, 1430,
1
1386, 1369, 1269, 1125, 1029, 770. H NMR spectrum,
δ, ppm: 2.05 m (2H, H9), 2.25 m (2H, H10), 2.78 m (2H,
H11), 3.73 s (3H, OMe), 5.13 s (1H, H7), 6.64 d, 6.77 d
(2H, H5', H6', 3J 7.5 Hz), 7.02 s (1H, H3'), 7.19–7.62 m,
7.76 m (5H, H2–6, 3J 7.9 Hz), 8.42 d (1H, H1, 3J 7.6 Hz),
9.14 s (1H, NH). Found, %: C 77.61; H 5.70; N 3.77.
C24H21NO3. Calculated, %: C 77.54; H 5.65; N 3.76.
7-(3,4-Dimethoxyphenyl)-10,11-dihydro-
benzo[c]-acridin-8(7H,9H,12H)-one (Vb). Yield 55%,
mp 236–238°C. IR spectrum, ν, cm–1: 3355, 3057, 3045,
2948, 2929, 2829, 1588, 1516, 1493, 1387, 1370, 1265,
1
1138, 1027, 752. H NMR spectrum, δ, ppm: 2.00 m
(2H, H9), 2.28 m (2H, H10), 2.81 m (2H, H11), 3.70 s
(6H, OMe), 5.19 s (1H, H7), 6.61 m (2H, H5', H6',
3J 7.5 Hz), 6.92 s (1H, H3'), 7.19–7.68 m, 7.76 m (5H,
H2–6, 3J 7.9 Hz), 8.45 d (1H, H1, 3J 7.6 Hz), 9.22 s (1H,
NH). Found, %: C 77.90; H 6.01; N 3.63. C25H23NO3.
Calculated, %: C 77.83; H 5.97; N 3.63.
7-(Benzo[d][1,3]dioxol-5-yl)-10,11-dihydro-
benzo[c]acridin-8(7H,9H,12H)-one (Vc). Yield 57%,
mp 262–264°C. IR spectrum, ν, cm–1: 3315, 3048, 3020,
2970, 2921, 2865, 1583, 1515, 1498, 1493, 1440, 1386,
1375, 1264, 1248, 1230, 1179, 1036, 752. 1H NMR
spectrum, δ, ppm: 1.98 m (2H, H9), 2.23 m (2H, H10),
2.82 m (2H, H11), 5.13 s (1H, H7), 5.83 s (2H, OCH2O)
6.65 s + d (3H, H3',H5', H6', 3J 7.5 Hz), 7.10–7.65 m (4H,
H2, H3, H5, H6, 3J 7.9 Hz), 7.76 d.d (1H, H4, 3J 7.9 Hz),
8.42 d.d (1H, H1, 3J 7.6 Hz), 9.20 C (1H, NH). Found,
EXPERIMENTAL
IR spectra were recorded on a IR Fourier
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 5 2010

KOZLOV et al.
744
OCOCH(CH3)2], 2.82 m (2H, H11), 3.73 s (3H, OMe),
5.28 s (1H, H7), 6.68 d, 6.85 d (2H, H5', H6', 3J 7.4 Hz),
7.10 s (1H, H3'), 7.40 d (1H, H6, 3J 7.6 Hz), 7.46–7.62 m
(3H, H2, H3, H5, 3J 7.4 Hz), 7.85 d (1H, H4, 3J 8.0 Hz),
8.50 d (1H, H1, 3J 7.4 Hz), 9.35 s (1H, NH). Found, %: C
76.17; H 6.16; N 3.17. C28H27NO4. Calculated, %: C
76.10; H 6.12; N 3.17.
%: C 78.03; H 5.18; N 3.79. C24H19NO3. Calculated, %:
C 77.96; H 5.14; N 3.79.
Compounds Vd–Vh. A solution of 2 mmol of
cyclohexane-1,3-dione (III) and 2 mmol of azomethine
IVd–IVh in 30 ml of butanol was boiled for 3–11 h. The
separated precipitate was filtered off and recrystallized
from benzene. If after boiling in butanol formed no
precipitate the solvent was evaporated, and the residue
was washed with acetone and recrystallized from
benzene.
4-(8-Oxo-7,8,9,10,11,12-hexahydrobenzo[c]-
acridin-7-yl)-2-methoxyphenyl benzoate (Vg). Yield
58%, mp 280–282°C. UV spectrum, λmax, nm (log ε):
223 (4.73), 258 (4.42), 281 (4.25), 372 (4.07). IR
spectrum, ν, cm–1: 3299, 3060, 3037, 2954, 2929, 2869,
1741, 1589, 1494, 1417, 1384, 1373, 1344, 1315, 1122,
1079, 1061, 1024, 710. 1H NMR spectrum, δ, ppm: 2.05
m (2H, H9, 2J 17.1 Hz), 2.30 m (2H, H10), 2.80 m (2H,
H11, 2J 16.8 Hz), 3.72 s (3H, OMe), 5.31 s (1H, H7), 6.72
d, 6.82 d (2H, H5', H6', 3J 7.0 Hz), 7.10 s (1H, H3'), 7.23–
7.92 m, 7.95–8.15 m (10H, H2–6, Harom, 3J 7.8 Hz), 8.46 d
(1H, H1, 3J 7.4 Hz), 9.26 C (1H, NH). Found, %: C 78.30;
H 5.30; N 2.95. C31H25NO4. Calculated, %: C 78.23;
H 5.26; N 2.94.
4-(8-Oxo-7,8,9,10,11,12-hexahydrobenzo[C]-
acridin-7-yl)-2-methoxyphenyl acetate (Vd). Yield
64%, mp 302–304°C. UV spectrum, λmax., nm (log ε):
218 (4.71), 258 (4.42), 281 (4.19), 368 (4.17). IR
spectrum, ν, cm–1: 3438, 3289, 3062, 3044, 2961, 2934,
2875, 1759, 1591, 1496, 1420, 1386, 1372, 1344, 1119,
1
1034, 791, 766, 742. H NMR spectrum, δ, ppm: 1.91–
2.35 m + s (4H, H9, H10 + 3H, OCOMe), 2.84 m (2H,
2
H11, J 16.9 Hz), 3.73 s (3H, OMe), 5.22 s (1H, H7),
6.64 d, 6.87 d (2H, H5’, H6’, 3J 7.5 Hz), 7.10 s (1H, H3’),
3
7.40–7.73 m, 7.85 br.d (5H, H2–6, J 7.9 Hz), 8.49 d.d
(1H, H1, 3J 7.6 Hz), 9.35 s (1H, NH). Found, %: C 75.53;
H 5.61; N 3.39 C26H23NO4. Calculated, %: C 75.46;
H 5.56; N 3.38.
4-(8-Oxo-7,8,9,10,11,12-hexahydrobenzo[c]-
acridin-7-yl)-2-ethoxyphenyl acetate (Vh). Yield 55%,
mp 313–315°C. UV spectrum, λmax, nm (log ε): 223
(4.34), 264 (4.12), 282 (3.92), 378 (3.74). IR spectrum,
ν, cm–1: 3311, 3073, 3038, 2956, 2928, 2872, 1767, 1578,
1514, 1493, 1430, 1386, 1369, 1269, 1125, 1029, 770.
1H NMR spectrum, δ, ppm: 1.34 t (3H, OCH2CH3),
4-(8-Oxo-7,8,9,10,11,12-hexahydrobenzo[C]-
acridin-7-yl)-2-methoxyphenyl propionate (Ve). Yield
50%, mp 291–293°C. UV spectrum, λmax, nm (log ε):
218 (4.41), 259 (4.09), 282 (3.75), 368 (3.83). IR
spectrum, ν, cm–1: 3440, 3283, 3062, 3042, 2961, 2933,
2872, 1761, 1591, 1497, 1417, 1384, 1373, 1343, 1122,
2
1.96 m (2H, H9, J 17.2), 2.18 m + s (2H, H10 + 3H,
OCOCH3), 2.70 m (2H, H11, 2J 16.9 Hz), 3.83 br.q (2H,
3
OCH2CH3, J 5.8 Hz), 5.26 C (1H, H7), 6.61 br.d,
1
1032, 792, 764, 740. H NMR spectrum, δ, ppm: 1.07 t
3
6.80 br.d (2H, H5', H6', J 7.7 Hz), 6.90 br.s (1H, H3'),
(3H, CH2CH3), 1.99 m (2H, H9, 2J 16.5 Hz), 2.30 m (2H,
H10), 2.50 q (2H, OCOCH2CH3, 3J 6.4 Hz), 2.85 m (2H,
7.17–7.70 m, 7.81 br.d (5H, H2–6, 3J 8.1 Hz), 8.50 br.d
(1H, H1, 3J 7.7 Hz), 9.23 s (1H, NH). Found, %: C 78.51,
H 5.56; N 2.86. C32H27NO4. Calculated, %: C 78.44;
H 5.52; N 2.86.
2
H11, J 16.2 Hz), 3.71 s (3H, OMe), 5.27 s (1H, H7),
6.68 d, 6.85 d (2H, H5', H6', 3J 7.4 Hz), 7.11 s (1H, H3'),
7.20 d (1H, H6, 3J 7.6 Hz), 7.46–7.62 m (3H, H2, H3, H5,
3J 7.4 Hz), 7.83 d (1H, H4, 3J 8.0 Hz), 8.47 d (1H, H1,
3J 7.4 Hz), 9.36 s (1H, NH). Found, %: C 75.86; H 5.89;
N 3.28. C27H25NO4. Calculated, %: C 75.79; H 5.85;
N 3.27.
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acridin-7-yl)-2-methoxyphenyl isobutyrate (Vf). Yield
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 5 2010

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