A. Bhalla et al. / Tetrahedron 62 (2006) 5054–5063
5061
d, J 11.4 Hz, CH H S); d (75 MHz, CDCl ) 156.4, 149.6,
a
128.7, 128.6, 127.6, 127.3, 127.0, 126.3, 119.6, 119.4,
118.8, 118.7, 117.3, 114.5, 114.1, 104.3, 103.6, 99.1, 98.4,
68.7, 66.5, 59.5, 55.4, 55.3, 54.0.
b
C
3
1
1
3
43.3, 136.7, 132.8, 131.0, 129.3, 128.9, 128.4, 128.3,
28.1, 127.0, 118.8, 114.4, 110.7, 109.6, 65.3, 63.1, 55.2,
4.6; dC (DEPT-135) (75 MHz, CDCl ) 143.3 (+), 129.3
3
0
0
0
4.5.19. 1-(4 -Methoxyphenyl)-3,3-bis(2 ,4 -dimethoxy-
phenyl)-4-(4 -methoxyphenyl)azetidin-2-one (10g).
(
1
+), 128.9 (+), 128.3 (+), 128.1 (+), 127.0 (+), 118.8 (+),
14.4 (+), 110.7 (+), 109.6 (+), 65.3 (+), 55.2 (+), 34.6 (ꢀ).
0
Brownish-yellow oil; yield 39%; [Found: C, 71.17; H,
0
0
5
2
1
.90; N, 2.47. C H NO requires C, 71.13; H, 5.98; N,
32 31 7
.52%]; R (10% EtOAc/hexane) 0.30; IR (cm , CHCl3):
f
736 (C]O); dH (300 MHz, CDCl ) 7.69–6.01 (14H, m,
3
4
.5.14. cis-1-(4 -Methoxyphenyl)-3-(3 -indolyl)-3-benzyl-
ꢀ
1
thio-4-phenylazetidin-2-one (9u). Reddish-brown oil; yield
7%; [Found: C, 75.84; H, 5.31; N, 5.67. C H N O S re-
quires C, 75.89; H, 5.34; N, 5.71%]; R (10% EtOAc/hexane)
1
3
1 26 2 2
Ph), 5.70 (1H, s, C4-H), 3.76 (3H, s, 2ꢂOCH ), 3.73 (3H,
3
f
ꢀ1
s, OCH ), 3.69 (3H, s, OCH ), 3.68 (3H, s, OCH ), 3.07
3
0
CDCl ) 8.12 (1H, br s, NH, D O exchangeable), 7.82–6.67
.43; IR (cm , CHCl ): 1764 (C]O); dH (300 MHz,
3
3
3
(3H, s, OCH ); d (75 MHz, CDCl ) 168.9, 160.7, 160.2,
3 C 3
3
2
1
1
6
58.8, 155.7, 132.3, 132.1, 130.1, 129.7, 128.9, 118.9,
18.7, 117.5, 114.1, 112.5, 104.2, 103.6, 99.1, 98.5, 68.7,
6.1, 55.9, 55.4, 55.3, 55.2, 54.2.
(
CH H S), 3.66 (3H, s, OCH ), 3.24 (1H, d, J 11.4 Hz,
19H, m, Ph), 5.10 (1H, s, C4-H), 3.87 (1H, d, J 11.4 Hz,
a
b
3
CH H S).
b
a
0
phenyl)-4-phenylazetidin-2-one (10h). Colourless crystal-
line solid; yield 38%; mp 268–270 C; [Found: C, 73.02;
0
0
0
-phenylazetidin-2-one (10a). Colourless crystalline solid;
0
4.5.20. 1-(4 -Methoxyphenyl)-3,3-bis(2 ,5 -dimethoxy-
4
.5.15. 1-(4 -Methoxyphenyl)-3,3-bis(4 -methoxyphenyl)-
4
yield 47%; mp 135–137 C; [Found: C, 77.47; H, 5.81; N,
ꢁ
ꢁ
H, 5.92; N, 2.61. C H NO requires C, 73.12; H, 5.96;
3
2
31
6
2
.96. C H NO requires C, 77.39; H, 5.86; N, 3.01%]; R
30 27 4 f
ꢀ
(10% EtOAc/hexane) 0.42; IR (cm , KBr):
f
1
ꢀ
1
N, 2.66%]; R
742 (C]O); dH (300 MHz, CDCl ) 7.42–6.27 (15H, m,
Ph), 5.84 (1H, s, C4-H), 3.77 (3H, s, OCH ), 3.73 (3H, s,
(
d (300 MHz, CDCl ) 7.54–6.53 (17H, m, Ph), 5.67 (1H,
10% EtOAc/hexane) 0.39; IR (cm , KBr): 1735 (C]O);
1
3
H
3
3
s, C4-H), 3.79 (3H, s, OCH ), 3.73 (3H, s, OCH ), 3.65
3
3
OCH ), 3.69 (3H, s, OCH ), 3.61 (3H, s, OCH ), 3.01 (3H,
3
3
3
(
3H, s, OCH ); d (75 MHz, CDCl ) 167.0, 158.8, 158.1,
3 C 3
s, OCH ); d (75 MHz, CDCl ) 167.9, 155.8, 153.4, 152.3,
3
C
3
1
1
5
56.1, 135.1, 133.3, 131.1, 129.7, 129.5, 128.4, 128.3,
28.1, 127.6, 118.7, 114.2, 114.1, 113.2, 71.2, 67.5, 55.3,
5.3, 55.0; m/z: 465 (M ).
150.8, 136.5, 132.1, 128.6, 127.1, 127.0, 125.1, 118.7,
118.0, 115.8, 114.1, 113.9, 113.1, 112.5, 110.7, 69.5, 66.3,
+
56.5, 55.8, 55.6, 55.4, 54.3.
0
-(4 -methoxyphenyl)azetidin-2-one (10b). Yellow oil;
0
4
4
.5.16. 1-(4 -Methoxyphenyl)-3,3-bis(4 -methoxyphenyl)-
0
0
-(4 -methoxyphenyl)azetidin-2-one (10i). Yellow oil;
0
4
4
.5.21. 1-(4 -Methoxyphenyl)-3,3-bis(4 -hydroxyphenyl)-
0
yield 42%; [Found: C, 75.21; H, 5.81; N, 2.76. C H NO
5
3
1
29
yield 36%; [Found: C, 74.57; H, 5.35; N, 2.97. C H NO
5
2
9
25
requires C, 75.14; H, 5.89; N, 2.83%]; R (10% EtOAc/hex-
f
requires C, 74.51; H, 5.39; N, 3.00%]; R (10% EtOAc/hex-
f
ꢀ
1
ane) 0.35; IR (cm , CHCl ): 1739 (C]O); d (300 MHz,
3
ꢀ1
H
ane) 0.29; IR (cm , CHCl ): 1725 (C]O), 3369 (OH),
3
CDCl ) 7.48–6.53 (16H, m, Ph), 5.58 (1H, s, C4-H), 3.77
3
3H, s, OCH ), 3.72 (3H, s, OCH ), 3.71 (3H, s, OCH ),
3 3 3
3383 (OH); dH (300 MHz, CDCl ) 7.32–6.43 (16H, m,
Ph), 5.61 (1H, s, C4-H), 3.71 (3H, s, OCH ), 3.66 (3H, s,
3
(
3
3
1
1
5
.67 (3H, s, OCH ); dC (75 MHz, CDCl ) 167.2, 159.4,
3 3
OCH ); d (75 MHz, CDCl ) 167.9, 159.3, 156.3, 155.2,
3
C
3
58.7, 158.1, 156.1, 133.6, 131.2, 129.8, 129.6, 128.9,
28.4, 127.1, 118.8, 114.3, 114.1, 113.8, 113.3, 71.1, 67.5,
5.4, 55.2.
1
1
54.5, 132.7, 130.8, 129.8, 129.2, 128.9, 128.6, 126.9,
19.0, 115.8, 114.9, 114.3, 113.8, 71.0, 67.7, 55.5, 55.2.
0 0
.5.22. 1-(4 -Methoxyphenyl)-3,3-bis(3 -indolyl)-4-phenyl-
azetidin-2-one (10v). Reddish-brown oil; yield 36%;
4
0
azetidin-2-one (10c). Colourless crystalline solid; yield
4
.5.17. 1-Benzyl-3,3-bis(4 -methoxyphenyl)-4-phenyl-
[Found: C, 79.59; H, 5.16; N, 8.65. C H N O requires C,
32 25 3
ꢁ
C H NO requires C, 80.15; H, 6.07; N, 3.11%]; R
3
5%; mp 145–147 C; [Found: C, 80.21; H, 6.01; N, 3.07.
79.64; H, 5.20; N, 8.69%]; R (10% EtOAc/hexane) 0.40;
IR (cm , CHCl ): 1762 (C]O); dH (300 MHz, CDCl3)
f
ꢀ1
3
0
27
3
f
3
ꢀ
1
(
d (300 MHz, CDCl ) 7.33–6.53 (18H, m, Ph), 5.06 (1H,
10% EtOAc/hexane) 0.35; IR (cm , KBr): 1741 (C]O);
7.35 (1H, br s, NH, D O exchangeable), 7.10 (1H, br s,
NH, D O exchangeable), 7.32–6.43 (19H, m, Ph), 5.63
2
H
3
2
s, C4-H), 4.95 (1H, d, J 15.2 Hz, CH H Ph), 3.90 (1H, d, J
a
b
(1H, s, C4-H), 3.76 (3H, s, OCH3).
1
OCH ); d (75 MHz, CDCl ) 170.2, 158.6, 158.1, 135.4,
4.9 Hz, CH H Ph), 3.76 (3H, s, OCH ), 3.66 (3H, s,
a b 3
0
0
3
C
3
4.5.23. 1-(4 -Methoxyphenyl)-3,3-bis(3 -pyrrolyl)-4-
phenylazetidin-2-one (10w). Black oil; yield 46%; [Found:
C, 75.14; H, 5.48; N, 10.91. C H N O requires C, 75.18;
1
1
35.1, 133.5, 129.6, 128.8, 128.6, 128.3, 128.1, 127.8,
14.0, 113.2, 72.0, 67.1, 55.3, 55.1, 44.3.
2
4 21 3 2
H, 5.52; N, 10.96%]; R (10% EtOAc/hexane) 0.35; IR
f
0
phenyl)-4-phenylazetidin-2-one (10f). Colourless crystal-
line solid; yield 43%; mp 175–177 C; [Found: C, 73.19;
0
0
ꢀ1
4
.5.18. 1-(4 -Methoxyphenyl)-3,3-bis(2 ,4 -dimethoxy-
(cm , CHCl ): 1743 (C]O); d (300 MHz, CDCl ) 8.51
3
H
3
(1H, br s, NH, D O exchangeable), 7.83 (1H, br s, NH,
2
D O exchangeable), 7.51–5.89 (15H, m, Ph), 5.58 (1H, s,
2
ꢁ
H, 5.90; N, 2.63. C H NO requires C, 73.12; H, 5.96;
3
2
31
6
C4-H), 3.73 (3H, s, OCH ); d (75 MHz, CDCl ) 165.1,
3
C
3
ꢀ1
N, 2.66%]; R (10% EtOAc/hexane) 0.35; IR (cm , KBr):
f
156.4, 134.3, 131.0, 128.7, 128.4, 127.4, 127.0, 124.8,
119.8, 118.9, 118.7, 118.4, 114.4, 108.8, 108.7, 108.3,
105.8, 67.6, 63.1, 55.5.
1
Ph), 5.75 (1H, s, C4-H), 3.77 (3H, s, OCH ), 3.75 (3H, s,
740 (C]O); dH (300 MHz, CDCl ) 7.71–5.95 (15H, m,
3
3
OCH ), 3.73 (3H, s, OCH ), 3.69 (3H, s, OCH ), 3.01 (3H,
3
3
3
0
phenylazetidin-2-one (11a). Colourless crystalline solid;
s, OCH ); d (75 MHz, CDCl ) 168.2, 160.4, 159.9, 158.5,
3
4.5.24. 1-(4 -Methoxyphenyl)-3,3-bis(phenylthio)-4-
C
3
1
55.9, 155.7, 136.8, 132.7, 132.3, 132.1, 130.2, 129.1,