10
ISMAIL AND EL-SAYED
υ/cm−1):3178 (br.) (OH), 2959, 2930, 2835 (CH3), 1620
(C N), 1597 (C C). H NMR (400 MHz, DMSO-d6) δ
(417.53): C, 69.04; H, 5.55; N, 10.06; S, 7.68. Found: C,
69.16; H, 5.58; N, 10.02; S, 7.61.
1
(ppm): 11.53 (s, 1H, OH, exchangeable with D2O), 7.74 to
7.72 (d, 2H, Ar0–H, Ho, J = 8.4 Hz), 7.71 to 7.70 (d, 2H,
0
0
0
Ar –H, Hm, J = 7.2 Hz), 7.55 to 7.53 (d, 2H, Ar –H, Ho ,
4.4.2 | 3-([1,10-biphenyl]-4-yl)-
5-(3,4-dimethoxyphenyl)-1-phenyl-
4,5-dihydro-1H-pyrazole 18
0
0
J = 8.4 Hz), 7.50 to 7.46 (t, 2H, Ar –H, Hm , J = 6.8 Hz,
J = 7.6 Hz), 7.49 to 7.46 (d, 1H, β CH , J = 16.8 Hz), 7.39
0
0
to 7.35 (t, 1H, Ar –H, Hp , J = 6.8 Hz, J = 7.6 Hz), 7.176
to 7.171 (d, 1H, Ar–H, Ho ’, Jm = 2 Hz), 7.10, 7.07 (d,d,
Yellow crystals; m.p.: 184ꢁC to 185ꢁC, yield 89%. IR (KBr,
υ/cm−1): 2959, 2934, 2833 (CHaliph.), 1595 (C N or C C).
1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.82 to 7.80 (d,
0
0
1H, Ar–H, Ho , Jm = 2 Hz, J = 8.4 Hz), 6.94 to 6.92 (d,
0
1H, Ar–H, Hm , J = 8.4 Hz), 6.75 to 6.71 (d,1H, α CH ,
J = 16.8 Hz), 3.96 (s, 3H, OCH3), 3.94 (s, 3H, OCH3). MS
m/z (%): 359 (M+; 57.83), 358 (91.49), 342 (100),
326 (9.59), 152 (6.40), 77 (4.35). Anal. Calcd for
C23H21NO3 (359.43): C, 76.86; H, 5.89; N, 3.90. Found: C,
76.89; H, 5.91; N, 3.89.
2H, Ar0–H, Ho, J = 8.4 Hz), 7.73 to 7.71 (d, 2H, Ar0–H,
0
0
Hm, J = 8.8 Hz), 7.71 to 7.69 (d, 2H, Ar –H, Ho ,
0
0
0
J = 8.8 Hz), 7.48 to 7.44 (t, 2H, Ar –H, Hm , J = 7.6 Hz,
0
J = 8 Hz), 7.38 to 7.34 (t, 1H, Ar –H, Hp , J = 6.8 Hz,
J = 7.6 Hz), 7.16 to 7.13 (t, 2H, NPh-H, Hm, J = 8.4 Hz,
J = 7.2 Hz), 7.04 to 7.02 (d, 2H, NPh-H, Ho, J = 7.6 Hz),
0
6.93 to 6.92 (d, 1H, Ar–H, Ho ’, Jm = 2.4 Hz), 6.88 to 6.86
0
4.4 | General procedure for preparation
of compounds 16 and 18
(d, 1H, Ar–H, Hm , J = 8.4 Hz), 6.77, 6.75 (d,d, 1H, Ar–H,
0
Ho , J = 1.6, J = 8.4 Hz), 6.73 to 6.69 (t, 1H, Nph-H, Hp,
J = 7.2 Hz, J = 7.6 Hz), 5.40, 5.37 (d,d, 1H, Ha, Jab = 12.0,
Jac = 6.8 Hz), 3.91, 3.87 (d,d, 1H, Hb, Jbc = 17.4,
Jba = 12.0 Hz), 3.69 (s, 3H, OCH3), 3.68 (s, 3H, OCH3),
3.15, 3.11 (d,d, 1H, Hc, Jcb = 17.2, Jca = 6.8 Hz). MS m/z
(%): 434 (M+; 100), 297 (0.70), 270 (1.33), 77 (1.90). Anal.
Calcd for C29H26N2O2 (434.54): C, 80.16; H, 6.03; N, 6.45.
Found: C, 80.12; H, 6.01; N, 6.48.
To a mixture of chalcone 3 (0.01 mol, 3.44 g), and
(thiosemicarbazide and/or phenyl hydrazine) (0.01 mol)
in an absolute ethanol (40 mL), a catalytic amount of
acetic acid was added (5 drops) and heated under stirring
for 6 hours. After cooling, the resulting solution was
poured slowly into crushed ice with stirring, the solid
deposited was collected by filtration, washed with water
several times, dried and further purification was done by
recrystallized from relevant solvent (ethanol and dioxane
for compounds 16 and 18, respectively).
4.4.3 | 4-([1,10-biphenyl]-4-yl)-
6-(3,4-dimethoxyphenyl)pyrimidine-2(1H)-
thione 19
4.4.1 | (E)-2-(1-([1,10-biphenyl]-4-yl)-
3-(3,4-dimethoxyphenyl)allylidene)
hydrazine-1-carbothioamide 16
To a mixture of chalcone 3 (0.01 mol, 3.44 g), and thio-
urea (0.76 g, 0.01 mol) in ethanol (40 mL), an aqueous
solution of sodium hydroxide (10 mL, 40%) was added
and heated under stirring for 6 hours. After cooling, the
resulting solution was neutralized by pouring slowly into
crushed ice cold water acidified by acetic acid with stir-
ring, The resulting solid was collected, washed with
water several times, dried and recrystallized from toluene
to give 19 as green crystals; m.p.: 240ꢁC to 242ꢁC, yield
62%. IR (KBr, υ/cm−1): 3387 (NH), 2999, 2932, 2834
Yellow crystals; m.p.: 186ꢁC to 188ꢁC, yield 66%. IR (KBr,
υ/cm−1):3447, 3328 (NH2), 3129 (NH), 2959, 2925, 2833
1
(CH3), 1600 (C N), 1587 (C C), 1264 (C S). H NMR
(400 MHz, DMSO-d6) δ (ppm): 10.87 (s, 1H, NH,
exchangeable with D2O), 8.27 (br.s, 2H, NH2, exchange-
able with D2O), 8.24 to 8.22 (d, 2H, Ar0–H, Ho, J = 8.4 Hz),
8.02 to 7.99 (d, 2H, Ar0–H, Hm, J = 8.4 Hz), 7.94 to 7.92
1
(CH3), 1623 (C N), 1600 (C C), 1264 (C S). H NMR
0
0
0
(d, 2H, Ar –H, Ho , J = 8.4 Hz), 7.71 to 7.37 (m, 3H, Ar –
(400 MHz, DMSO-d6) δ (ppm): 11.89 (br.s, 1H, NH,
exchangeable with D2O), 8.38 to 7.09 (m, 12H, 9Ar0–H
+ 3Ar–H), 6.65 (s, 1H, C5–H(pyrimidinethione)), 3.87 (s, 3H,
OCH3), 3.84 (s, 3H, OCH3). MS m/z (%): 400 (M+; 100),
399 (91.58), 384 (67.02), 383 (66.36), 341 (23.68),
311 (26.12), 280 (12.38), 193 (22.27), 180 (8.53),
152 (17.69), 77 (11.74), 44 (39.30). Anal. Calcd for
C24H20N2O2S (400.50): C, 71.98; H, 5.03; N, 6.99; S, 8.01.
Found: C, 72.07; H, 5.07; N, 7.02; S, 7.92.
0
0
H, 2Hm + Hp ), 7.65 to 7.61 (d,1H, β CH , J = 15.6 Hz),
0
7.28, 7.26 (d,d, 1H, Ar–H, Ho , Jm = 2 Hz, Jo = 8.4 Hz),
0
7.10 to 7.09 (d, 1H, Ar–H, Ho ’, Jm = 1.6 Hz), 6.97 to 6.95
0
(d, 1H, Ar–H, Hm , Jo = 8.4 Hz), 6.80 to 6.76 (d,1H, α
CH , J = 15.6 Hz), 3.80 (s, 3H, OCH3), 3.77 (s, 3H,
OCH3). MS m/z (%): 417 (M+; 100), 416 (75.26),
384 (30.39), 357 (30.54), 221 (6.23), 179 (4.80), 152 (6.08),
77 (5.61), 60 (18.34). Anal. Calcd for C24H23N3O2S