(
4Н, m, 2СН
2
); 2.54-2.70 (1Н, m) and 3.07 (1Н, t, J = 11.4, СН ); 3.66 (1Н, d, J = 14.6) and 3.98 (1Н, d,
2
1
3
J = 13.3, СН
2
); 7.28-7.48 (7Н, m, Н Ph); 7.57 (1Н, t, J = 7.4, Н Ph,); 7.98 (2Н, d, J = 7.6, Н Ph). С NMR
spectrum, δ, ppm: 25.3, 29.5, 38.9, 65.0 (4СН ); 96.8 (C-9а); 125.3, 128.3, 128.9, 129.0, 129.1, 129.5, 133.8,
2
+
1
36.7 (С Ph); 163.9 (C=O); 185.2 (C=N). Mass spectrum, m/z (I , %): 306 [M] (11), 203 (100), 175 (21), 147
rel
(
28), 117 (30), 105 (63). Found, %: C 74.46; H 5.95; N 9.16. C H N O . Calculated, %: C 74.49; H 5.92;
1
9
18
2
2
N 9.14.
8
,8a-Bis(4-methoxyphenyl)-3,4-2H-imidazo[5,1-b][1,3]oxazin-6(8aH)-one (9b). 63% HNO (10 ml)
3
was added dropwise to a suspension of 1-(3-hydroxypropyl)-4,5-bis(4-methoxyphenyl)-1H-imidazol-2(3H)-one
11b) (3.54 g, 0.01 mol) in MeCN (35 ml). The reaction was monitored by the change in color and by the
(
dissolution of the precipitate. The reaction mixture was extracted with a 1:1 CHCl –H O mixture, the
3
2
chloroform layer was evaporated, and the residue was rubbed with Et O. Yield 2.18 g (70%), white powder, mp
2
1
1
88-190°C. H NMR spectrum, δ, ppm (J, Hz): 1.50-1.60 (1Н, m) and 1.61-1.80 (1Н, m, CH
2
); 2.80-3.00 (1Н,
); 3.79 (3Н, s, OСН ); 6.93-7.05
4Н, m, Н Ar); 7.39 (2Н, t, J = 8.6, Н Ar); 8.03 (2Н, d, J = 8.8, Н Ar). С NMR spectrum, δ, ppm: 24.4, 36.0
2СН ); 55.1, 55.5 (2OСН ); 62.8 (CH ); 93.5 (C-9а); 112.1, 113.1, 114.3, 114.8, 120.9, 125.1, 126.4, 128.4,
29.3, 130.8, 131.9, 159.7 (С Ar); 163.4 (C=O); 184.6 (C=N). Found, m/z: 375.1305 [M+Na] . C20
m) and 3.50-3.67 (1H, m, CH
2
); 3.69-3.76 (2H, m, CH
2
); 3.73 (3Н, s, OСН
3
3
1
3
(
(
1
2
3
2
+
H
20
N
2
NaO
4
.
+
Calculated, m/z: 375.1315 [M+Na] .
-(2-Hydroxyethyl)-4,5-bis(4-methoxyphenyl)-1H-imidazol-2(3H)-one (11a). Ethylene glycol (10 ml)
was added to a mixture of 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone (10) (2.72 g, 0.01 mol) and the urea
1
3
a (5.20 g, 0.05 mol). The mixture was stirred at 160°C for 1 h. It was then extracted with a 1:1 CHCl –H O
3
2
mixture, the chloroform layer was evaporated, and the residue was rubbed with Et O. Yield 2.38 g (70%), white
2
1
powder, mp 214-216°C. H NMR spectrum, δ, ppm (J, Hz): 3.30-3.50 (4Н, m, 2СН
2
); 3.68 (3Н, s, OСН ); 3.80
3
(
3Н, s, OСН
Н Ar); 10.67 (1Н, s, NН). С NMR spectrum, δ, ppm: 42.9 (CH
14.5; 117.0; 119.2; 121.8; 122.5; 126.7; 128.3; 132.4; 153.3 (C=O); 157.8, 159.4 (2C–OMe). Found, %:
C 67.07; H 5.94; N 8.21. C H N O . Calculated, %: C 67.05; H 5.92; N 8.23.
3
); 4.48 (1H, s, OH); 6.78 (2Н, d, J = 8.4, Н Ar); 6.98-7.12 (4Н, m, Н Ar); 7.28 (2Н, d, J = 8.4,
13
2
); 55.1 (2OСН
3
); 58.9 (CH ); 113.9; 114.1;
2
1
1
9
20
2
4
1
-(3-Hydroxypropyl)-4,5-bis(4-methoxyphenyl)-1H-imidazol-2(3H)-one (11b). This compound was
obtained similarly from compound 10 (5.44 g, 0.02 mol) and the urea 3b (11.80 g, 0.10 mol). Yield 0.86 g
1
(
(
(
12%), white powder, mp 218-220°C. H NMR spectrum, δ, ppm (J, Hz): 1.40-1.60 (2Н, m, СН
2Н, m, СН ); 3.40-3.52 (2Н, m, СН ); 3.68 (3Н, s, OСН ); 3.80 (3Н, s, OСН ); 4.47 (1H, t, J = 4.9, OH); 6.78
2Н, d, J = 8.5, Н Ar); 6.98-7.12 (4Н, m, Н Ar); 7.28 (2Н, d, J = 8.5, Н Ar); 10.66 (1Н, s, NН). С NMR
); 55.0, 55.1 (2OСН ); 58.1 (CH ); 113.4; 114.5; 117.1; 118.9; 121.8; 122.4;
26.6; 132.2; 153.2 (C=O); 157.8, 159.4 (2C–OMe). Found, %: C 67.75; H 6.27; N 7.92. C20
Calculated, %: C 67.78; H 6.26; N 7.90.
3aR*,10aS*)-3,3a,10,10a-Tetrakis(4-methoxyphenyl)-5,6,12,13-tetrahydrodiimidazo[5,1-b:5',1'-g]-
2
); 3.20-3.31
2
2
3
3
1
3
spectrum, δ, ppm: 32.3, 37.7 (2CH
2
3
2
1
H
22
N
2
4
O .
(
[
1,6,3,8]dioxadiazecine-1,8(3aH,10aH)-dione (12). 63% HNO (20 ml) was added dropwise to a suspension of
3
compound 11a (8.50 g, 0.025 mol) in MeCN (30 ml). The reaction was monitored by the change in color and by
the dissolution of the precipitate. The reaction mixture was extracted with a 1:1 CHCl –H O mixture, the
3
2
chloroform layer was evaporated, and the residue was rubbed with Et O. Yield 1.85 g (22%), white powder, mp
2
1
>
CH
355°C. H NMR spectrum, δ, ppm (J, Hz): 2.43-2.60 (2Н, m, CH
2
); 2.98-3.07 (2Н, m, CH
); 4.00-4.25 (2Н, m, CH ); 7.02 (8H, d, J = 8.6, Н Ar);
.19-7.35 (4H, m, Н Ar); 7.95 (4H, d, J = 8.7, Н Ar). С NMR spectrum, δ, ppm: 55.2, 55.7 (4OСН ); 55.9,
2
); 3.62-3.70 (2H, m,
2
); 3.79 (6Н, s, 2OСН
3
); 3.88 (6Н, s, 2OСН
3
2
1
3
7
5
1
3
8.4 (4CH
2
); 96.7 (O–C–Ar); 114.9, 120.5, 126.3, 126.4 131.5, 132.0 (С Ar); 159.7 (C–OMe); 164.0 (C=O);
+
+
83.5 (C=N). Found, m/z: 677.2593 [M+Н] . C38
H
37
N
4
O
8
. Calculated, m/z: 677.2606 [M+Н] .
1
-(2-Hydroxyethyl)-6-methyl-3a,6a-diphenyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
(
(
13a). Conc. HCl (0.1 ml) was added to a solution of compound 2a (0.296 g, 1 mmol) and N-methylurea (3c)
0.074 g, 1 mmol) in MeCN (10 ml). The mixture was refluxed for 20 min. When the reaction mixture had
5
10