TOLPYGIN et al.
1308
N2-(Anthracen-9-ylmethyl)naphthalene-2,3-
Fluorescence spectrum (acetonitrile): λmax 480 nm (c =
5×10–5 M): 480. Found, %: C 86.00; H 5.27; N 5.60.
C36H26N2O. Calculated, %: C 86.03; H 5.21; N 5.57.
diamine (II). Sodium tetrahydridoborate, 0.9 g
(25 mmol), was added under stirring to a hot solution
of 1.7 g (5 mmol) of Schiff base I in 100 ml of EtOH–
DMF (3:2). The mixture was stirred for 2 h and
diluted with water, and the precipitate was filtered off,
washed with water, dried in air, and recrystallized from
butan-1-ol–DMF (3:1) with addition of activated char-
coal. Yield 1.5 g (86%), mp 262–263°C. IR spectrum,
2-[3-(Anthracen-9-ylmethylamino)naphthalen-2-
yliminomethyl]naphthalen-1-ol (IIIc) was synthe-
sized from amine II and 1-hydroxynaphthalene-2-car-
baldehyde. Yield 84%, mp 246–247°C (from butan-1-
ol–DMF, 3:1). IR spectrum, ν, cm–1: 1610, 1460,
1
1375. H NMR spectrum (CDCl3), δ, ppm: 4.70 br.s
1
ν, cm–1: 1590, 1500, 1460, 1435. H NMR spectrum
(1H, NH), 5.38 s (2H, CH2), 6.80 d (1H, Harom, J =
(DMSO-d6), δ, ppm: 4.88 br.s (2H, NH2), 5.10–
5.30 br.s (3H, CH2, NH), 6.87 s (1H, Harom), 7.00–
7.17 m (3H, Harom), 7.35–7.62 m (6H, Harom), 8.07 d
(2H, Harom, J = 7.4 Hz), 8.30 d (2H, Harom, J = 7.4 Hz),
8.54 s (1H, Harom). Fluorescence spectrum (acetoni-
trile): λmax 413 nm (c = 5 × 10–5 M). Found, %:
C 86.18; H 5.82; N 8.00. C25H20N2. Calculated, %:
C 86.18; H 5.78; N 8.04.
7.4 Hz), 7.00–8.20 m (17H, Harom), 8.34 d (2H, Harom
,
J = 8.0 Hz), 8.50 s (1H, Harom), 8.72 s (1H, CH),
13.68 s (1H, OH). No fluorescence was observed in
acetonitrile. Found, %: C 85.94; H 5.23; N 5.62.
C36H26N2O. Calculated, %: C 86.03; H 5.21; N 5.57.
1-(Anthracen-9-ylmethyl)-2-(pyridin-2-yl)-1H-
naphtho[2,3-d]imidazole (IV). Amine II, 0.17 g
(0.5 mmol), was dissolved in 10 ml of butan-1-ol–
DMF (3 : 1), 0.05 ml of acetic acid and 0.1 ml
(1.0 mmol) of pyridine-2-carbaldehyde were added,
the mixture was heated for 1 h, the solvent was dis-
tilled off under reduced pressure, and the residue was
recrystallized from butan-1-ol. Yield 0.14 g (64%),
mp 256–257°C (from butan-1-ol). IR spectrum, ν, cm–1:
Schiff bases IIIa–IIIc (general procedure). Amine
II, 0.17 g (0.5 mmol), was dissolved in 10 ml of a 3:1
butan-1-ol–DMF mixture, 0.05 ml of acetic acid and
0.5 mmol of the corresponding aldehyde were added,
the mixture was heated for 30 min and cooled, and the
precipitate was filtered off and recrystallized from
appropriate solvent.
1
1600, 1465, 1380. H NMR spectrum (DMSO-d6), δ,
ppm: 6.88 s (1H, CH2), 7.08–7.30 m (5H, Harom, CH2),
7.33–7.52 m (5H, Harom), 7.80–8.10 m (4H, Harom),
8.20 s (1H, Harom), 8.40–8.53 m (4H, Harom), 8.68–
8.74 m (1H, Harom). Fluorescence spectrum (aceto-
nitrile): λmax 455 nm (c = 5×10–5 M). Found, %:
C 85.55; H 4.82; N 9.63. C31H21N3. Calculated, %:
C 85.49; H 4.86; N 9.65.
2-[3-(Anthracen-9-ylmethylamino)naphthalen-2-
yliminomethyl]-4-methylphenol (IIIa) was synthe-
sized from amine II and 2-hydroxy-5-methylbenzalde-
hyde. Yield 78%, mp 247–248°C (from butan-1-ol–
DMF, 3:1). IR spectrum, ν, cm–1: 1600, 1467, 1380.
1H NMR spectrum (CDCl3), δ, ppm: 2.24 s (3H, CH3),
4.63 br.s (1H, NH), 5.35 s (2H, CH2), 6.50–6.73 m
(2H, Harom), 7.10–7.60 m (9H, Harom), 7.70–7.90 m
(2H, Harom), 8.05 d (2H, Harom, J = 7.8 Hz), 8.30 d (2H,
Harom, J = 7.8 Hz), 8.52 s (1H, Harom), 8.60 s (1H, CH),
12.07 s (1H, OH). Fluorescence spectrum (aceto-
nitrile): λmax 487 nm (c = 5×10–5 M). Found, %:
C 84.90; H 5.68; N 5.95. C33H26N2O. Calculated, %:
C 84.95; H 5.62; N 6.00.
1-(Anthracen-9-ylmethyl)-2,3-dihydro-1H-
naphtho[2,3-d]imidazole-2-thione (V). A solution of
0.5 g (1.5 mmol) of amine II in 2 ml (13 mmol) of
phenyl isothiocyanate was heated for 1 h. The mixture
was cooled, and the precipitate was filtered off and
recrystallized from butan-1-ol–DMF. Yield 0.5 g
(84%), mp 244–245°C (from butan-1-ol). IR spectrum,
1
ν, cm–1: 3170, 1455, 1445, 1380. H NMR spectrum
1-[3-(Anthracen-9-ylmethylamino)naphthalen-2-
yliminomethyl]naphthalen-2-ol (IIIb) was synthe-
sized from amine II and 2-hydroxynaphthalene-1-car-
baldehyde. Yield 87%, mp 302–303°C (from butan-1-
ol–DMF, 3:1). IR spectrum, ν, cm–1: 1600, 1460,
(DMSO-d6), δ, ppm: 6.40 s (2H, CH2), 6.60 s (1H,
H
H
arom), 6.80–7.22 m (3H, Harom), 7.40–7.77 m (6H,
arom), 8.11 d (2H, Harom, J = 7.8 Hz), 8.64 s (1H,
Harom), 8.72 d (2H, Harom, J = 7.8 Hz), 12.93 s (1H,
NH). Fluorescence spectrum (MeCN): λmax 418 nm
(c = 5×10–5 M). Found, %: C 80.05; H 4.71; N 7.09;
S 8.15. C26H18N2S. Calculated, %: C 79.97; H 4.65;
N 7.17; S 8.21.
1
1385. H NMR spectrum (CDCl3), δ, ppm: 4.78 br.s
(1H, NH), 5.38 s (2H, CH2), 6.94 d (1H, Harom, J =
8.7 Hz), 7.20–7.57 m (10H, Harom), 7.66–7.90 m (4H,
H
H
arom), 8.04 d (2H, Harom, J = 7.9 Hz), 8.14 d (1H,
arom, J = 8.2 Hz), 8.32 d (2H, Harom, J = 7.8 Hz),
This study was performed under financial support
by the Russian Foundation for Basic Research (project
8.49 s (1H, Harom), 9.46 s (1H, CH), 14.05 s (1H, OH).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 9 2011