NEW CARBAZOLE-CONTAINING CHALCONES
535
15.0 Hz), 7.42–7.45 m (3H, thiophene, carbazole),
7.65 d (1H, carbazole, J = 6.9 Hz), 7.78 d (1H, carba-
zole, J = 6.9 Hz), 7.91 d (1H, carbazole, J = 8.4 Hz),
8.03 d (1H, CH=, J = 15.0 Hz), 8.36 s (1H, carbazole).
Found, %: C 75.97; H 4.01; S 9.73. C21H17NOS. Cal-
culated, %: C 76.10; H 4.23; S 9.67.
%: C 84.11; H 6.32; N 6.0. C33H30N2O. Calculated, %:
C 84.22; H 6.43; N 5.95.
3-(9-Butyl-9H-carbazol-3-yl)-1-(9-ethyl-9H-car-
bazol-3-yl)prop-2-en-1-one (XVII). Yield 72%,
1
mp 161–163°C. H NMR spectrum, δ, ppm: 0.95 t
(3H, CH3, J = 6.9 Hz), 1.37–1.49 m (5H, CH3, CH2),
1.82–1.92 m (2H, CH2), 4.29–4.44 m (4H, NCH2),
7.26–7.33 m (2H, carbazole), 7.44–7.54 m (6H, carba-
zole, CH=), 7.79–7.86 m (2H, carbazole), 8.13 d (1H,
CH=, J = 15.6 Hz), 8.18–8.29 m (2H, carbazole),
8.42 s (1H, carbazole), 8.89 s (1H, carbazole).
1,3-Bis(9-butyl-9H-carbazol-3-yl)prop-2-en-1-
one (XIII). Yield 62%, mp 223–225°C. 1H NMR spec-
trum, δ, ppm: 0.95 m (6H, CH3), 1.37–1.44 m (4H,
CH2), 1.87–1.91 m (4H, CH2), 4.28–4.37 m (4H, CH2),
7.17–7.39 m (3H, Harom), 7.40–7.54 m (5H, Harom),
7.76–7.86 m (2H, Harom), 8.00 d (1H, COCH=, J =
15.9 Hz), 8.09–8.29 m (3H, Harom), 8.40 d (1H, CH=,
J = 16.5 Hz), 8.89 s (1H, Harom). Found, %: C 84.19;
H 5.78. C35H34N2O. Calculated, %: C 84.30; H 5.62.
3,3′-(1,4-Phenylene)bis[1-(9-ethyl-9H-carbazol-
3-yl)prop-2-en-1-one] (XVIII). Yield 72%, decompo-
1
sition point 210°C. H NMR spectrum, δ, ppm: 1.48 t
(6H, CH3, J = 6.9 Hz), 4.44 q (4H, CH2, J = 6.9 Hz),
7.27–7.34 m (4H, carbazole), 7.45–7.53 m (6H, carba-
zole), 7.78 s (4H, C6H4), 7.86 d (2H, carbazole), 8.20–
8.27 m (4H, carbazole), 8.87 s (2H, carbazole). Found,
%: C 83.51; H 5.50; N 5.02. C40H32N2O2. Calculated,
%: C 83.69; H 5.63; N 4.89.
1-(9-Butyl-9H-carbazol-3-yl)-3-(2-thienyl)prop-
2-en-1-one (XIV). Yield 74%, mp 110–112°C.
1H NMR spectrum, δ, ppm: 0.94 t (3H, CH3, J =
7.5 Hz), 1.41 m (2H, CH2), 1.87 m (2H, CH2), 4.33 t
(2H, CH2, J = 7.2 Hz), 7.09 t (1H, thiophene, J =
3.6 Hz), 7.29 t (1H, carbazole), 7.36–7.79 m (6H, thio-
phene, carbazole), 7.54 d (1H, CH=, J = 15.3 Hz),
8.00 d (1H, COCH=, J = 15.5 Hz), 8.02 d (2H, carba-
zole, J = 8.1 Hz), 8.8 s (1H, carbazole). Mass spec-
trum, m/z (Irel, %): 360.2 (26.3) [M]+, 359.2 (100), 331
(16), 317 (21), 316.1 (90), 288.1 (16), 179 (16).
C23H21NOS. M 249.48.
4,6-Diarylpyrimidin-2-amines XIX–XXII (gen-
eral procedure). A mixture of 3.7 mmol of the corre-
sponding chalcone, 0.56 g (2.6 mmol) of guanidine
sulfate (2:1 salt), 20 ml of ethanol, and 3 ml of 50%
aqueous potassium hydroxide was heated for 1 h under
reflux, 10 ml of hydrogen peroxide was added drop-
wise over a period of 30 min to the boiling mixture, the
mixture was poured into cold water, and the precipitate
was filtered off and purified by column chromatog-
raphy using acetone–hexane (1:2) as eluent.
3-(9-Butyl-9H-carbazol-3-yl)-1-(2-thienyl)prop-
2-en-1-one (XV). Yield 67%, mp 99–101°C. 1H NMR
spectrum, δ, ppm: 0.95 t (3H, CH3, J = 7.2 Hz), 1.40 m
(2H, CH2, J = 7.5 Hz), 1.88 m (2H, CH2), 4.32 t (2H,
CH2, J = 7.0 Hz), 7.2 t (1H, thiophene, J = 3.6 Hz),
7.25–7.31 m (1H, carbazole), 7.42 d (2H, carbazole,
J = 8.4 Hz), 7.47 d (1H, CH=, J = 15.6 Hz), 7.66 d
(1H, thiophene, J = 4.8 Hz), 7.78 d (1H, carbazole, J =
8.4 Hz), 7.91 d (1H, thiophene, J = 4.2 Hz), 8.08 d
(1H, COCH=, J = 15.6 Hz), 8.14 d (1H, carbazole, J =
7.5 Hz), 8.38 s (1H, carbazole). Found, %: C 76.75;
H 5.53; N 4.01; S 8.84. C23H21NOS. Calculated, %:
C 76.85; H 5.89; N 3.90; S 8.95.
4,6-Bis(9-ethyl-9H-carbazol-3-yl)pyrimidin-2-
1
amine (XIX). Yield 30%, mp 161–163°C. H NMR
spectrum, δ, ppm: 1.45 t (6H, CH3), 4.45 q (4H, CH2),
5.23 s (2H, NH2), 7.27–7.34 m (3H, carbazole, 5-H),
7.39–7.53 m (6H, carbazole), 8.11–8.17 m (4H, carba-
zole), 8.74 s (2H, carbazole). Found, %: C 79.69;
H 5.52; N 14.60. C32H27N5. Calculated, %: C 79.81;
H 5.65; N 14.54.
4-(4-Bromophenyl)-6-(9-ethyl-9H-carbazol-3-yl)-
1
pyrimidin-2-amine (XX). Yield 42%. H NMR spec-
trum, δ, ppm: 1.39 t (3H, CH3), 4.19–4.22 q (2H, CH2),
5.05 br.s (2H, NH2), 7.50–7.53 m (6H, 5-H, C6H4,
carbazole), 7.68–7.71 m (5H, carbazole, C6H4). Found,
%: C 64.95; H 4.18; N 12.80. C24H19BrN4. Calculated,
%: C 65.02; H 4.32; N 12.64.
1-(9-Butyl-9H-carbazol-3-yl)-3-(9-ethyl-9H-car-
bazol-3-yl)prop-2-en-1-one (XVI). Yield 70%,
1
mp 169–170°C. H NMR spectrum, δ, ppm: 0.96 t
(3H, CH3, J = 6.9 Hz), 1.36–1.49 m (5H, CH3, CH2),
1.86–1.94 m (2H, CH2), 4.30–4.43 m (4H, NCH2),
7.26–7.34 m (3H, carbazole), 7.45–7.54 m (6H, carba-
zole, CH=), 7.80–7.88 m (2H, carbazole), 8.13 d (1H,
CH=, J = 15.6 Hz), 8.13–8.30 m (2H, carbazole),
8.44 s (1H, carbazole), 8.90 s (2H, carbazole). Found,
4-(9-Ethyl-9H-carbazol-3-yl)-6-ferrocenylpyrim-
idin-2-amine (XXI). Yield 40%. 1H NMR spectrum, δ,
ppm: 1.46 t (3H, CH3), 4.23 (5H, Fc), 4.38 m (2H,
NCH2), 4.57 s (2H, Fc), 4.96 s (2H, Fc), 5.15 br.s (2H,
NH2), 7.38–7.53 m (4H, carbazole, 5-H), 7.79 d (1H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 4 2011