Synthesis of 2-Aryl-3H-naphtho[1,2-d]imidazoles containing an adamantane fragment

Article abstract of DOI:10.1134/S1070428013120075

N2-[1-(1-Adamantyl)alkyl]naphthalene-1,2-diamines reacted with benzoyl chlorides in chloroform in the presence of triethylamine to give N-{2-[1-(1-adamantyl)alkylamino]naphthalen-1-yl}benzamides which underwent intramolecular cyclization to 2-aryl-3H-naph

Full text of DOI:10.1134/S1070428013120075

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 12, pp. 1748–1752. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © T.A. Frolenko, E.S. Semichenko, A.A. Kondrasenko, N.A. Gavrilova, G.A. Suboch, 2013, published in Zhurnal Organicheskoi
Khimii, 2013, Vol. 49, No. 12, pp. 1768–1772.
Synthesis of 2-Aryl-3H-naphtho[1,2-d]imidazoles
Containing an Adamantane Fragment
T. A. Frolenkoa, E. S. Semichenkoa, A. A. Kondrasenkob, N. A. Gavrilovaa, and G. A. Subocha
a Siberian State Technological University, pr. Mira 82, Krasnoyarsk, 660049 Russia
e-mail: organic@sibgtu.ru
b Institute of Chemistry and Chemical Technology, Siberian Branch, Russian Academy of Sciences,
Akademgorodok 50/24, Krasnoyarsk, 660036 Russia
Received August 22, 2012
Abstract—N2-[1-(1-Adamantyl)alkyl]naphthalene-1,2-diamines reacted with benzoyl chlorides in chloroform
in the presence of triethylamine to give N-{2-[1-(1-adamantyl)alkylamino]naphthalen-1-yl}benzamides which
underwent intramolecular cyclization to 2-aryl-3H-naphtho[1,2-d]imidazoles on heating in toluene in the pres-
ence of p-toluenesulfonic acid. 3-[(1-Adamantyl)methyl]-2-(3-nitrophenyl)-3H-naphtho[1,2-d]imidazole was
synthesized from N2-[(1-adamantyl)methyl]naphthalene-1,2-diamine and 3-nitrobenzaldehyde.
DOI: 10.1134/S1070428013120075
Some 3H-naphtho[1,2-d]imidazoles were reported
as nonsteroidal antiinflammatory agents [1]; they also
exhibited antihypertensive activity [2]. It is known that
introduction of an aromatic substituent into the 2-posi-
tion of 3H-naphtho[1,2-d]imidazoles may enhance bio-
logical activity [2] and that the presence of a lipophilic
adamantyl fragment in their molecules facilitates pene-
tration through biological membranes [3]. We previ-
ously synthesized N2-[1-(1-adamantyl)alkyl]naphtha-
lene-1,2-diamines Ia and Ib by reduction of
N-[1-(1-adamantyl)alkyl]-1-nitrosonaphthalen-2-
amines, and compounds Ia and Ib were then used to
obtain 2-alkyl-3H-naphtho[1,2-d]imidazoles possess-
ing an adamantane fragment [4]. While continuing our
studies on heterocyclizations of naphthalene-1,2-di-
amines Ia and Ib, in the present work we examined
their reactions with benzoyl chlorides IIa and IIb
(Scheme 1).
By heating diamines Ia and Ib with benzoyl
chlorides IIa and IIb and triethylamine in chloroform
we obtained the corresponding benzamides IIIa–IIIc.
13
In the C NMR spectra of IIIb and IIIc (CDCl3), the
carbonyl carbon signal appeared at δC 165–167 ppm.
Benzamides IIIa–IIIc were subjected to intramolec-
ular cyclization to previously unknown 2-aryl-3H-
naphtho[1,2-d]imidazoles IVa–IVc by heating in
boiling toluene in the presence of p-toluenesulfonic
acid. The progress of the cyclization was monitored by
TLC. After removal of the solvent, the products were
isolated by column chromatography.
Diamines Ia and Ib readily undergo oxidation;
therefore, it is advisable to perform their benzoylation
in situ immediately after the reduction of N-[1-(1-ada-
mantyl)alkyl]-1-nitrosonaphthalen-2-amines Va and
Vb with hydrazine hydrate over Pd/C in chloroform
(Scheme 2). Following this procedure, we have synthe-
Scheme 1.
Ar
Ar
NH2
O
NH
N
R
H
H
O
N
Et3N
TsOH, PhMe, Δ
N
R
N
R
+
–Et3N·HCl
–H2O
Ad
Ar
Cl
Ad
Ad
Ia, Ib
IIa, IIb
IIIa–IIIc
IVa–IVc
I, R = H (a), Me (b); II, Ar = Ph (a), 4-ClC6H4 (b); III, IV, R = H, Ar = Ph (a); R = Me, Ar = Ph (b), 4-ClC6H4 (c).
1748

SYNTHESIS OF 2-ARYL-3H-NAPHTHO[1,2-d]IMIDAZOLES
1749
Scheme 2.
O
NO
Ar
NH
N2H4·H2O
Pd/C, CHCl3
ArCOCl (IIa–IId)
Et3N, CHCl3
H
H
PhMe, Δ
N
R
N
R
Ia, Ib
IVa–IVg
–N2, –H2O
–Et3N·HCl
–H2O
Ad
Ad
Va, Vb
A
V, R = H (a), Me (b); IV, R = H (a, d–f), Me (b, c, g); Ar = Ph (a, b), 4-ClC6H4 (c, d), 4-O2NC6H4 (e), 3-O2NC6H4 (f, g).
Scheme 3.
NO2
PhH, Δ
Pd/C, Δ
HN
Ia
+
IVf
–H2O
–H2
N
O2N
CHO
Ad
B
sized 2-aryl-3H-naphtho[1,2-d]imidazoles IVa–IVg.
3-Alkyl-2-aryl-3H-naphtho[1,2-d]imidazoles were
successfully obtained previously via condensation of
aromatic aldehydes with naphthalene-1,2-diamines and
subsequent dehydrogenation [1]. We examined the
reaction of compound Ia with 3-nitrobenzaldehyde
(Scheme 3) and thus isolated a compound which was
identical to 3H-naphtho[1,2-d]imidazole IVf synthe-
sized from diamine Ia and 3-nitrobenzoyl chloride.
signals in the spectra of IVf and IVg were assigned on
the basis of calculations of chemical shifts according to
the additivity scheme with the following increments
for the nitro group: Zortho = 0.93, Zpara = –0.39 [6].
EXPERIMENTAL
1
13
The H and C NMR spectra were recorded at the
Krasnoyarsk Regional Joint Center (Siberian Branch,
Russian Academy of Sciences) on a Bruker Avance III
spectrometer (600.13 and 125.86 MHz, respectively) at
223 K using the solvent signals as reference (for atom
numbering in the description of the NMR spectra, see
figure). The mass spectra were obtained on a Finnigan
MAT-8200 mass spectrometer. GC/MS analyses were
performed on an Agilent Technologies 6890N instru-
ment (HP-5MS quartz capillary column, 30 m×
0.25 mm, film thickness 0.33 μm; electron impact,
70 eV); the components were identified in the total ion
current mode.
The mass spectra of compounds IVa, IVb, and IVf
contained the molecular ion peaks with m/z values cor-
responding to the assumed structure. In addition, a ion
peak with m/z 135 due to adamantyl cation was ob-
served; its further fragmentation gave ions with m/z 93
and 79, which are typical of 1-alkyl-substituted ada-
mantanes regardless of the alkyl group nature [5]. The
elemental compositions of IVc–IVe and IVg were
consistent with the calculated values.
Compounds IVa and IVd–IVf displayed in the
1H and 13C NMR spectra signals from the AdCH2
methylene group at δ 4.19–4.25 ppm (s) and δC 56.1–
56.5 ppm. The corresponding fragment in the spectra
of IVc and IVg was represented by a doublet at
δ 1.9 ppm (CH3, δC 13 ppm) and a quartet at δ 4.4 ppm
(CH, δC 62 ppm). Signals from the adamantyl substit-
uent were also present. Signals from the benzene and
The products were isolated by column chromatog-
raphy on Silicagel L 100/400 (Chemapol). Analytical
thin-layer chromatography was performed on Sorbfil
PTSKh-AF-V plates with a UV indicator; eluent
heptane–ethyl acetate (9:1).
Naphthalene-1,2-diamines Ia and Ib were synthe-
sized according to the procedure described in [7].
1
naphthalene fragments were assigned using H–1H
COSY, HMBC, and HSQC homo- and heteronuclear
correlation techniques (see figure). The 4′-H and 6′-H
N-{2-[1-(1-Adamantyl)alkylamino]naphthalen-
1-yl}benzamides IIIa–IIIc (general procedure).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 12 2013

FROLENKO et al.
1750
H
R
O2N
H
H
H
3'
3'
3'
4'
4'
4'
2'
2'
2'
H
N
H
H
H
H
N
H
5'
5'
5'
1'
1'
1'
6'
6'
6'
H
H
H
N
R
N
N
N
Ad
Ad
Ad
R = H, Me
Ar
R = Cl, NO2
H
R1
N
4
N
H
H
1"
4"
6
9
5
13
12
*
7
8
7"
6"
10
3"
11
2"
5"
10"
H
8"
*
*
H
H
9"
IVc
1H–1H COSY, 1H–13C HSQC, and 1H–13C HMBC correlations in compounds IVa and IVc–IVg. Weak 1H–13C HMBC correlations in
IVc are marked with an asterisk.
A mixture of 1.6 mmol of naphthalene-1,2-diamine Ia
or Ib, 3 mmol of benzoyl chloride IIa or IIb, and
0.22 mL (1.5 mmol) of triethylamine in 30 mL of
chloroform was heated for 2 h under reflux (TLC). The
solution was evaporated under reduced pressure, and
the residue was purified by chromatography in a 2×
50-cm column charged with 50 g of silica gel using
hexane–ethyl acetate (9:1) as eluent.
N-{2-[1-(1-Adamantyl)ethylamino]naphthalen-
1-yl}-4-chlorobenzamide (IIIc). Yield 0.46 g (66%),
light yellow crystals soluble in acetone, ethanol, and
1
chloroform; mp 170°C. H NMR spectrum, δ, ppm:
1.16 d (3H, CH3, J = 6.35 Hz), 1.51–1.73 m (12H,
CH2, Ad), 2.00 m (3H, CH, Ad), 3.31 m (1H, CH),
7.21–7.24 m (2H, 3-H, 7-H), 7.41–7.44 m (1H, 8-H),
7.55 m (2H, 3′-H, 5′-H), 7.61–7.64 m (1H, 9-H), 7.74–
7.76 m (2H, 4-H, 6-H), 8.00 m (2H, 2′-H, 6′-H).
13C NMR spectrum, δC, ppm: 15.1 (CH3), 28.4 (3C,
CH, Ad), 37.2 (3C, CH2, Ad), 36.8 (C, Ad), 38.8 (3C,
CH2, Ad), 57.7 (CH), 112.1 (C1), 115.1 (C3), 119.8
(C9), 121.9 (C7), 127.0 (C10), 127.2 (C8), 128.7 (C2′,
C6′), 128.4 (C4), 128.7 (C6), 129.3 (C3′, C5′), 131.7 (C5),
138.4 (C4′), 132.6 (C1′), 143.0 (C2), 165.6 (C=O).
Found, %: C 75.48; H 6.16; Cl 7.61 N 6.83.
C29H31ClN2O. Calculated, %: C 75.88; H 6.81;
Cl 7.72; N 6.10.
N-{2-[(1-Adamantyl)methylamino]naphthalen-
1-yl}benzamide (IIIa). Yield 0.43 g (65%), light
yellow crystals soluble in acetone, ethanol, and chloro-
form; mp 169°C. Found, %: C 82.15; H 6.94; N 6.43.
C28H30N2O. Calculated, %: C 81.91; H 7.37; N 6.82.
N-{2-[1-(1-Adamantyl)ethylamino]naphthalen-
1-yl}benzamide (IIIb). Yield 0.37 g (57%), light
yellow crystals soluble in acetone, ethanol, and chloro-
1
form; mp 168°C. H NMR spectrum, δ, ppm: 1.16 d
(3H, CH3, J = 6.77 Hz), 1.51–1.73 m (12H, CH2, Ad),
2.02 m (3H, CH, Ad), 3.31 m (1H, CH), 7.21–7.24 m
(2H, 3-H, 7-H), 7.42 m (1H, 8-H), 7.56–7.61 m (3H,
3′-H, 5′-H, 9′-H), 7.64–7.66 m (1H, 4′-H), 7.74–7.76 m
(2H, 4-H, 6-H), 8.07 m (2H, 2′-H, 6′-H). 13C NMR
spectrum (CDCl3), δC, ppm: 15.2 (CH3), 28.5 (3C, CH,
Ad), 37.2 (3C, CH2, Ad), 36.8 (C, Ad), 38.8 (3C, CH2,
Ad), 57.8 (CH), 112.1 (C1), 115.1 (C3), 120.0 (C9),
121.8 (C7), 127.3 (C10), 127.3 (C2′, C6′, C8), 128.0 (C6,
C4), 129.0 (C3′, C5′), 131.8 (C5), 132.0 (C4′), 134.5 (C1′)
143.6 (C2), 166.6 (C=O). Found, %: C 82.27; H 7.14;
N 6.33. C29H32N2O. Calculated, %: C 82.04; H 7.60;
N 6.60.
2-Aryl-3H-naphtho[1,2-d]imidazoles IVa–IVf
(general procedure). a. A mixture of 0.6 mmol of
benzamide IIIa–IIIc and 0.05 g of p-toluenesulfonic
acid in 30 mL of toluene was heated for 48 h under
reflux. The mixture was cooled, washed with a 5% so-
lution of sodium carbonate and water, and evaporated,
and the residue was purified by column chromatog-
raphy (2×50 cm) on 50 g of silica gel using hexane–
ethyl acetate (4:1) as eluent.
b. To a mixture of 1.6 mmol of compound Va or Vb
and 0.5 g of 0.5% Pd/C in 30 mL of chloroform we
added under vigorous stirring 0.3 mL (7.2 mmol) of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 12 2013

SYNTHESIS OF 2-ARYL-3H-NAPHTHO[1,2-d]IMIDAZOLES
1751
95% hydrazine hydrate, and the mixture was stirred for
1 h. The catalyst was filtered off, 3 mmol of benzoyl
chloride IIa–IId and 0.22 mL (1.5 mmol) of triethyl-
amine were added in succession to the filtrate, and the
mixture was heated for 2 h under reflux. The mixture
was then evaporated under reduced pressure on
a rotary evaporator, 30 mL of toluene was added to the
residue, and the mixture was heated for 48 h under
reflux, filtered, and evaporated. An analytical sample
of the product was obtained by chromatographic
purification in a 2×50-cm column charged with 50 g
of silica gel using hexane–ethyl acetate (4:1) as eluent.
(C2′, C6′), 129.8 (C13), 131.3 (C1′), 131.6 (C3′, C5′),
135.3 (C4′), 152.3 (C2). Found, %: C 79.27; H 6.59;
Cl 8.00; N 6.38. C29H29ClN2. Calculated, %: C 78.98;
H 6.63; Cl 8.04; N 6.35.
3-[(1-Adamantyl)methyl]-2-(4-chlorophenyl)-
3H-naphtho[1,2-d]imidazole (IVd). Yield 0.27 g
1
(40%) (b), mp 230°C. H NMR spectrum, δ, ppm:
1.30–1.71 m (12H, CH2, Ad), 1.85 m (3H, CH, Ad),
4.19 s (2H, CH2), 7.54 m (1H, 8-H), 7.55 m (2H, 2′-H,
6′-H), 7.61 m (1H, 12-H), 7.67 m (1H, 7-H), 7.71 m
(2H, 3′-H, 5′-H), 7.98 m (1H, 9-H), 8.74 m (1H, 6-H).
13C NMR spectrum, δC, ppm: 28.1 (C5″, C6″, C7″), 36.4
(C8″, C9″, C10″), 36.9 (C1″), 41.2 (C2″, C3″, C4″), 56.2
(CH2), 112.2 (C12), 121.9 (C6 ), 123.5 (C11 ), 124.7
(C8 ), 126.6 (C7), 127.0 (C5), 128.3 (C9), 129.1 (C2′,
C6′), 130.2 (C10), 130.8 (C1′), 131.2 (C3′, C5′), 133.1
(C13 ), 135.3 (C4′, C4), 151.2 (C2). Found, %: C 79.17;
H 6.54; Cl 8.16; N 6.23. C28H27ClN2. Calculated, %:
C 78.76; H 6.37; Cl 8.30; N 6.56.
3-[(1-Adamantyl)methyl]-2-phenyl-3H-naphtho-
[1,2-d]imidazole (IVa). Yield 0.15 g (64%) (a), 0.13 g
(21%) (b); light yellow crystals soluble in acetone,
1
ethanol, and chloroform; mp 230°C. H NMR spec-
trum, δ, ppm: 1.30–1.75 m (12H, CH2, Ad), 1.84 m
(3H, CH, Ad), 4.22 s (2H, CH2), 7.52 m (1H, 4′-H),
7.53 m (1H, 8-H), 7.55 m (2H, 2′-H, 6′-H), 7.62 d (1H,
12-H), 7.66 m (1H, 7-H), 7.73 d (1H, 11-H), 7.75 m
(2H, 3′-H, 5′-H), 7.97 m (1H, 9-H), 8.77 m (1H, 6-H).
13C NMR spectrum, δC, ppm: 28.1 (C5″, C7″), 36.4 (C8″,
C9″, C10″), 36.9 (C1″), 41.1 (C2″, C3″, C4″), 56.1 (CH2),
112.3 (C12), 122.0 (C6), 123.2 (C11), 124.5 (C8), 126.4
(C7), 127.0 (C5), 128.3 (C9), 128.7 (C2′, C6′), 129.1
(C4′), 130.2 (C10), 130.1 (C3′, C5′), 132.3 (C1′), 133.1
(C4, C13), 152.5 (C2). Mass spectrum, m/z (Irel, %): 392
(9) [M]+, 135 (20), 93 (15), 79 (100), 55 (38). Found,
%: C 85.90; H 7.22; N 7.21 C28H28N2. Calculated, %:
C 85.67; H 7.19; N 7.14. M 392.54.
3-[(1-Adamantyl)methyl]-2-(4-nitrophenyl)-3H-
naphtho[1,2-d]imidazole (IVe). Yield 0.3 g (43%) (b),
yellow crystals soluble in acetone, ethanol, and chloro-
1
form; mp 220°C. H NMR spectrum, δ, ppm: 1.28–
1.60 m (12H, CH2, Ad), 1.84 m (3H, CH, Ad), 4.23 s
(2H, CH2), 7.56 m (1H, 8-H), 7.62 m (1H, 12-H, J =
8.9 Hz), 7.69 m (1H, 7-H), 7.77 m (1H, 11-H), 7.97 m
(2H, 2′-H, 6′-H), 7.98 m (1H, 9-H), 8.42 m (2H, 3′-H,
5′-H), 8.74 m (1H, 6-H). 13C NMR spectrum, δC, ppm:
28.0 (C5″, C6″, C7″), 36.3 (C8″, C9″, C10″), 37.1 (C1″),
41.2 (C2″, C3″, C4″), 56.5 (CH2), 112.1 (C12), 121.8
(C6), 124.0 (C3′, C5′), 124.3 (C11), 125.0 (C8), 126.9
(C7), 127.0 (C5), 128.4 (C9), 130.4 (C10), 130.7 (C2′,
C6′), 133.6 (C1′), 138.4 (C13), 138.7 (C4), 147.9 (C4′),
149.7 (C2). Found, %: C 77.24; H 5.89; N 9.13.
C28H27N3O2. Calculated, %: C 76.86; H 6.22; N 9.60.
3-[1-(1-Adamantyl)ethyl]-2-phenyl-3H-naphtho-
[1,2-d]imidazole (IVb). Yield 0.14 g (57%) (a), 0.4 g
(35%) (b); mp 168°C. Mass spectrum, m/z (Irel, %):
406 (7) [M]+, 327 (5), 178 (10), 135 (100), 113 (12), 93
(25), 79 (18), 67 (5), 55 (5), 44 (12), 32 (11). Found,
%: C 85.70; H 7.47; N 7.05. C29H30N2. Calculated, %:
C 85.67; H 7.44; N 6.89. M 406.57.
3-[(1-Adamantyl)methyl]-2-(3-nitrophenyl)-3H-
naphtho[1,2-d]imidazole (IVf). Yield 0.55 g (80%)
(b), 0.21 g (31%) (according to [1]); light yellow
crystals soluble in acetone, ethanol, and chloroform,
and DMSO; mp 158°C. 1H NMR spectrum, δ, ppm: in
CDCl3: 1.30–1.61 m (12H, CH2, Ad), 1.86 m (3H, CH,
Ad), 4.25 s (2H, CH2), 7.56–7.58 m (1H, 8-H), 7.63 m
(1H, 12-H), 7.69 m (1H, 7-H), 7.77–7.79 m (2H, 5-H,
11-H), 7.97 m (1H, 9-H), 8.18–8.19 m (1H, 6′-H),
8.40 m (1H, 4′-H), 8.66 s (1H, 2′-H), 8.75 br.s (1H,
6-H); in DMSO-d6: 1.21 m (6H, CH2, Ad), 1.32–
1.49 m (6H, CH2, Ad), 1.71(3H, CH, Ad), 4.35 s (2H,
CH2), 7.50–7.54 m (1H, 8-H), 7.6–7.66 m (1H, 7-H),
7.78–7.81 m (1H, 12-H), 7.85–7.90 m (1H, 5′-H),
7.93–7.96 m (1H, 11-H), 8.01–8.04 m (1H, 9-H), 8.32–
3-[1-(1-Adamantyl)ethyl]-2-(4-chlorophenyl)-
3H-naphtho[1,2-d]imidazole (IVc). Yield 0.13 g
(51%) (a), 0.13 g (31%) (b); light yellow crystals
soluble in acetone, ethanol, and chloroform;
1
mp 171°C. H NMR spectrum, δ, ppm: 1.30–1.71 m
(12H, CH2, Ad), 1.85 m (3H, CH, Ad), 4.19 s (2H,
CH2), 7.54 m (1H, 8-H), 7.55 m (2H, 2′-H, 6′-H),
7.61 m (1H, 12-H), 7.67 m (1H, 7-H), 7.71 m (2H,
3′-H, 5′-H), 7.98 m (1H, 9-H), 8.74 m (1H, 6-H).
13C NMR spectrum, δC, ppm: 13.7 (CH3), 28.2 (C5′,
C7″), 36.5 (C8′, C9″, C10″), 39.4 (C1″), 39.9 (C2″, C3″,
C4″), 62.7 (CH), 115.0 (C12), 122.0 (C6), 122.8 (C11),
124.7 (C8), 126.4 (C7), 127.1 (C10), 128.0 (C9), 129.0
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 12 2013

FROLENKO et al.
1752
8.35 m (1H, 6′-H), 8.37–8.40 m (1H, 4′-H), 8.50–
8.53 m (1H, 6-H), 8.64 s (1H, 2′-H). C NMR spec-
125.2 (C8), 126.9 (C7), 128.1 (C9), 130.0 (C4, C5′, C1′),
136.3 (C6′). Found, %: C 77.47; H 5.96; N 8.83.
C29H29N3O2. Calculated, %: C 77.13; H 6.47; N 9.31.
13
trum, δC, ppm: 28.0 (C5″, C6″, C7″), 36.3 (C8″, C9″, C10″),
37.1 (C1″), 41.2 (C2″, C3″, C4″), 56.5 (CH2), 112.1 (C12),
121.9 (C6), 123.9 (C4′), 124.2 (C11), 124.6 (C2′), 125.0
(C8), 126.9 (C7), 127.0 (C10), 128.4 (C9), 130.0 (C5′),
130.4 (C1′), 133.3 (C13), 135.9 (C6′), 148.3 (C4), 149.5
(C3′, C2). Mass spectrum, m/z (Irel, %): 437 (70) [M]+,
407 (100), 281 (15), 259 (15), 207 (30), 156 (27), 135
(30), 114 (12), 93 (20), 79 (18), 67 (12), 55 (5), 44
(13). Found, %: C 77.05; H 6.40; N 9.74. C28H27N3O2.
Calculated, %: C 76.86; H 6.22; N 9.60. M 437.54.
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(b), light yellow crystals soluble in acetone, ethanol,
4. Gavrilova, N.A., Frolenko, T.A., Semichenko, E.S., and
Suboch, G.A., Russ. J. Org. Chem., 2010, vol. 46, p. 777.
1
and chloroform; mp 148°C. H NMR spectrum, ppm:
5. Dolejsek, Z., Halo, S., Hanus, V., and Lande, S., Collect.
Czech. Chem. Commun., 1966, vol. 2, p. 435.
1.44–1.60 m (12H, CH2, Ad), 1.91 m (3H, CH, Ad),
1.91–1.95 d (3H, CH3, J = 7.40 Hz), 4.41 q (1H, CH),
7.56 m (1H, 8-H), 7.68 m (1H, 7-H), 7.73 m (1H,
11-H), 7.78 m (1H, 5′-H) 7.83 (1H, 12-H), 7.97 m (1H,
9-H), 8.06 m (1H, 6′-H), 8.41 m (1H, 4′-H), 8.56 m
(1H, 2′-H), 8.75 (1H, 6-H). 13C NMR spectrum, δC,
ppm: 13.7 (CH3), 28.1 (C5″, C6″, C7″), 36.4 (C8″, C9″,
C10″), 39.5 (C1″), 39.9 (C2″, C3″, C4″), 63.3 (CH), 114.9
(C12), 122.1 (C6), 123.8 (C4′), 124.2 (C11), 125.2 (C2′),
6. Structure Determination of Organic Compounds: Tables
of Spectral Data, Pretsch, E., Bühlmann, P., and Af-
folter, C., Eds., Berlin: Springer, 2000, 3rd ed. Translated
under the title Opredelenie stroeniya organicheskikh
soedinenii. Tablitsy spektral’nykh dannykh, Moscow:
Mir, 2006, pp. 188, 189.
7. Semichenko, E.S., Gomonova, A.L., Gavrilova, N.A., and
Suboch, G.A., Russ. J. Org. Chem., 2008, vol. 44, p. 647.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 12 2013