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10067
m, CH]CHaHb), 4.98 (1H, s, C4–H), 2.80–2.74 (2H, m, CH2CH]),
2.15 (3H, s, CH3S), 2.01 (3H, s, CH3); dC (75 MHz, CDCl3) (DEPT-135)
166.2, 134.8, 133.6, 132.3 (þ), 129.5 (þ), 128.4 (þ), 127.9 (þ), 127.5
(þ), 119.6 (ꢁ), 117.2 (þ), 64.1, 63.8 (þ), 37.6 (ꢁ), 20.8 (þ), 11.8 (þ),
11.7 (þ).
4.4.22. 1-Benzyl-3,3-bis(20,50-dimethoxyphenyl)-4-(40-methoxyphen
yl)-azetidin-2-one (7m). White semisolid (0.002 g, 4%); [Found: C,
73.40; H, 6.08; N, 2.64. C33H33NO6 requires: C, 73.45; H, 6.16; N,
2.60%]; Rf (10% EtOAc/hexane) 0.32; IR (cmꢁ1, CHCl3): 1740 (C]O);
dH (300 MHz, CDCl3) 7.32–6.20 (15H, m, Ph), 5.37 (1H, s, C4–H), 4.57
(1H, d, J 14.4 Hz, PhCHaHb), 3.82 (1H, d, J 14.4 Hz, PhCHaHb), 3.73
(3H, s, OCH3), 3.64 (3H, s, OCH3), 3.48 (3H, s, OCH3), 3.27 (3H, s,
OCH3), 2.86 (3H, s, OCH3); dC (75 MHz, CDCl3) 168.3, 159.2, 153.4,
153.4, 150.3, 135.1, 134.3, 130.7, 129.6, 129.4, 128.3, 128.0, 127.5,
126.9, 125.4, 114.9, 114.7, 113.6, 113.2, 112.9, 112.7, 67.6, 55.8, 55.6,
55.5, 55.4, 55.2, 45.9.
4.4.16. (ꢂ)-trans-1-(40-Methoxyphenyl)-3-(20,50-dimethoxyphenyl)-
3-methylthio-4-phenylazetidin-2-one (6k). Colourless oil (0.004 g,
7%); [Found: C, 68.82; H, 5.69; N, 3.14. C25H25NO4S requires: C,
68.94; H, 5.79; N, 3.22%]; Rf (10% EtOAc/hexane) 0.34; IR (cmꢁ1
,
CCl4): 1747 (C]O); dH (300 MHz, CDCl3) 7.43–6.62 (12H, m, Ph),
4.97 (1H, s, C4–H), 3.70 (3H, s, OCH3), 3.67 (3H, s, OCH3), 3.62 (3H, s,
OCH3), 2.16 (3H, s, CH3S); dC (75 MHz, CDCl3) 164.9, 155.6, 153.4,
151.0, 133.5, 131.4, 129.0, 128.3, 127.5, 126.7, 118.3, 114.8, 114.4, 112.9,
66.2, 64.2, 55.9, 55.5, 55.2, 12.9.
4.4.23. 1-(40-Methoxyphenyl)-3,3-bis(40-hydroxyphenyl)-4-phenyl-
azetidin-2-one (7o). Yellow oil (0.007 g, 12%); [Found: C, 76.92; H,
5.27; N, 3.24. C28H23NO4 requires: C, 76.87; H, 5.30; N, 3.20%]; Rf
(10% EtOAc/hexane) 0.31; IR (cmꢁ1, CHCl3): 1723 (C]O), 3375 (OH);
dH (300 MHz, CDCl3) 7.26–6.31 (19H, m, Ph, OH), 5.54 (1H, s, C4–H),
3.64 (3H, s, OCH3); dC (75 MHz, CDCl3) 169.7, 154.0, 132.8, 130.7,
128.8, 127.6, 126.4, 126.2, 125.9, 125.4, 116.7, 113.5, 112.6, 112.1, 69.0,
65.5, 55.3.
4.4.17. (ꢂ)-trans-1-Phenyl-3-(20,50-dimethoxyphenyl)-3-methylthio-
4-phenylazetidin-2-one (6l). Yellow oil (0.004 g, 6%); [Found: C,
70.94; H, 5.61; N, 3.34. C24H23NO3S requires: C, 71.08; H, 5.72; N,
3.45%]; Rf (10% EtOAc/hexane) 0.36; IR (cmꢁ1, CCl4): 1750 (C]O); dH
(300 MHz, CDCl3) 7.47–6.82 (13H, m, Ph), 5.35 (1H, s, C4–H), 3.87
(3H, s, OCH3), 3.82 (3H, s, OCH3), 2.05 (3H, s, CH3S); dC (75 MHz,
CDCl3) 165.1, 153.9, 151.0, 137.4, 133.6, 129.0, 128.4, 128.1, 127.3,
126.2, 123.6, 117.3, 115.1, 114.7, 113.4, 66.3, 64.1, 55.7, 55.2, 12.6.
4.4.24. 1-Phenyl-3,3-bis(40-hydroxyphenyl)-4-phenylzetidin-2-one
(7p). Yellow oil (0.013 g, 20%); [Found: C, 79.64; H, 5.20; N, 3.50.
C27H21NO3 requires: C, 79.59; H, 5.19; N, 3.44%]; Rf (10% EtOAc/
hexane) 0.33; IR (cmꢁ1, CHCl3): 1729 (C]O), 3362 (OH); dH
(300 MHz, CDCl3) 7.36–6.37 (20H, m, Ph, OH), 5.64 (1H, s, C4–H); dC
(75 MHz, CDCl3) 167.9, 155.0, 154.2, 139.4, 137.4, 134.8, 129.7, 129.4,
129.0, 128.6, 128.3, 128.1, 127.5, 124.2, 117.5, 115.6, 114.7, 71.1, 67.4.
4.4.18. (ꢂ)-trans-1-Phenyl-3-(40-hydroxyphenyl)-3-methylthio-4-
phenylazetidin-2-one (6p). Yellow oil (0.003 g, 6%); [Found: C,
73.14; H, 5.15; N, 3.75. C22H19NO2S requires: C, 73.10; H, 5.30; N,
3.88%]; Rf (10% EtOAc/hexane) 0.39; IR (cmꢁ1, CCl4): 1747 (C]O),
3382 (OH); dH (300 MHz, CDCl3) 7.49–6.48 (15H, m, Ph, OH), 5.00
(1H, s, C4–H), 2.04 (3H, s, CH3S); dC (75 MHz, CDCl3) 166.4, 155.6,
137.4, 133.2, 130.1, 129.2, 128.9, 128.4, 127.4, 124.6, 117.5, 115.1, 68.1,
64.5, 13.2.
4.4.25. 1-Benzyl-3,3-bis(30-pyrrolyl)-4-(40-methoxyphenyl)azetidin-
2-one (7t). Black semisolid (0.034 g, 60%); [Found: C, 75.50; H,
5.79; N, 10.54. C25H23N3O2 requires: C, 75.54; H, 5.83; N, 10.57%]; Rf
(10% EtOAc/hexane) 0.31; IR (cmꢁ1, CHCl3): 1746 (C]O), 3367 (NH);
dH (300 MHz, CDCl3) 8.03 (1H, br s, NH, D2O exchangeable), 7.89
(1H, br s, NH, D2O exchangeable), 7.25–5.69 (15H, m, Ph, 2C4H3NH),
4.82 (1H, d, J 15.0 Hz, CHaHbPh), 4.75 (1H, s, C4–H), 3.72 (1H, d, J
15.0 Hz, CHaHbPh), 3.67 (3H, s, OCH3); dC (75 MHz, CDCl3) 168.3,
159.6,135.1,128.9,128.8,128.6,128.4,127.8,126.0,124.9,118.1,118.0,
113.6, 108.8, 108.6, 108.2, 105.0, 66.8, 63.4, 55.1, 44.4.
4.4.19. (ꢂ)-trans-1-(40-Methoxyphenyl)-3-(20-furanyl)-3-methyl-
thio-4-phenylazetidin-2-one (6q). Yellow oil (0.004 g, 6%); [Found:
C, 68.90; H, 5.15; N, 3.75. C21H19NO3S requires: C, 69.02; H, 5.24; N,
3.83%]; Rf (10% EtOAc/hexane) 0.40; IR (cmꢁ1, CCl4): 1745 (C]O); dH
(300 MHz, CDCl3) 7.35–6.76 (9H, m, Ph), 6.99 (1H, dd, J 0.9, 1.8 Hz,
C4HaHbHcO), 6.39 (1H, dd J 0.6, 2.1 Hz, C4HaHbHcO), 6.04 (1H, dd, J
1.8, 3.3 Hz, C4HaHbHcO), 4.99 (1H, s, C4–H), 3.67 (3H, s, OCH3), 2.15
(3H, s, CH3S); dC 163.9, 156.2, 148.5, 143.7, 132.4, 130.2, 128.8, 128.4,
127.9, 127.6, 127.2, 118.1, 114.0, 110.2, 109.6, 64.4, 62.4, 55.2, 13.0.
4.4.26. 1-(40-Methoxyphenyl)-3,3-bis(methylthio)-4-phenylazetidin-
2-one (8a). White solid (0.002 g, 4%); mp 77–78 ꢀC; [Found: C,
62.51; H, 5.48, N, 4.01. C18H19NO2S2 requires: C, 62.58; H, 5.54; N,
4.05%]; Rf (10% EtOAc/hexane) 0.57; IR (cmꢁ1, CCl4): 1759 (C]O); dH
(300 MHz, CDCl3) 7.28–6.65 (9H, m, Ph), 4.96 (1H, s, C4–H), 3.65
(3H, s, OCH3), 2.28 (3H, s, CH3S), 1.81 (3H, s, CH3S); dC (75 MHz,
CDCl3) 162.1, 156.4, 133.1, 130.7, 129.0, 128.3, 128.1, 118.7, 114.4, 70.9,
68.5, 55.2, 13.1, 12.1.
4.4.20. (ꢂ)-trans-1-Benzyl-3-(20-furanyl)-3-methylthio-4-(40-me-
thoxyphenyl)azetidin-2-one (6r). Yellow oil (0.004 g, 9%); [Found: C,
69.52; H, 5.47; N, 3.58. C22H21NO3S requires: C, 69.63; H, 5.58; N,
3.69%]; Rf (10% EtOAc/hexane) 0.38; IR (cmꢁ1, CCl4): 1760 (C]O); dH
(300 MHz, CDCl3) 7.28–6.62 (9H, m, Ph), 7.00 (1H, dd, J 0.6, 1.8 Hz,
C4HaHbHcO), 6.36 (1H, dd, J 0.6, 3.3 Hz, C4HaHbHcO), 6.05 (1H, dd, J
1.8, 3.3 Hz, C4HaHbHcO), 4.73 (1H, d, J 15.0 Hz, CHaHbPh), 4.56 (1H, s,
C4–H), 3.79 (1H, d, J 14.7 Hz, CHaHbPh), 3.67 (3H, s, OCH3), 2.04 (3H,
s, CH3S); dC (75 MHz, CDCl3) 166.0, 159.8, 149.4, 146.7, 143.3, 134.9,
129.8, 128.8, 128.5, 127.8, 125.6, 113.7, 111.5, 109.8, 64.2, 63.5, 54.9,
44.2, 12.9.
4.4.27. 1-Phenyl-3,3-bis(methylthio)-4-phenylazetidin-2-one
(8b). White semisolid (0.002 g, 6%); [Found: C, 64.65; H, 5.39; N,
4.46. C17H17NOS2 requires: C, 64.73; H, 5.43; N, 4.44%]; Rf (10%
EtOAc/hexane) 0.58; IR (cmꢁ1, CHCl3): 1753 (C]O); dH (400 MHz,
CDCl3): 7.35–7.09 (10H, m, Ph), 5.15 (1H, s, C4–H), 2.36 (3H, s, CH3S),
1.93 (3H, s, CH3S); dC (100 MHz, CDCl3) 163.9, 134.4, 130.5, 130.2,
129.3, 128.7, 128.4, 118.6, 114.2, 72.4, 68.1, 13.4, 12.5.
4.4.21. 1-Benzyl-3,3-bis(40-methoxyphenyl)-4-(40-methoxy-
phenyl)azetidin-2-one (7i). White semisolid (0.004 g, 9%); [Found:
C, 77.58; H, 6.02; N, 2.95. C31H29NO4 requires: C, 77.64; H, 6.10; N,
2.92%]; Rf (10% EtOAc/hexane) 0.30; IR (cmꢁ1, CHCl3): 1740 (C]O);
dH (300 MHz, CDCl3) 7.18–6.46 (17H, m, Ph), 4.85 (1H, s, C4–H), 4.82
(1H, d, J 14.7 Hz, CHaHbPh), 3.70 (1H, d, J 15.0 Hz, CHaHbPh), 3.68
(3H, s, OCH3), 3.67 (3H, s, OCH3), 3.61 (3H, s, OCH3); dC (75 MHz,
CDCl3) 168.7, 160.1, 159.5, 158.2, 133.9, 130.1, 129.7, 129.3, 129.1,
128.9, 128.4, 127.2, 126.3, 114.8, 114.6, 114.0, 113.7, 67.9, 55.9, 55.7,
55.5, 44.6.
4.4.28. 1-Benzyl-3,3-bis(methylthio)-4-(40-methoxyphenyl)azetidin-
2-one (8c). White semisolid (0.002 g, 4%); [Found: C, 63.40; H,
5.75; N, 3.81. C19H21NO2S2 requires: C, 63.48; H, 5.89; N, 3.90%]; Rf
(10% EtOAc/hexane) 0.56; IR (cmꢁ1, CHCl3): 1767 (C]O); dH
(400 MHz, CDCl3) 7.52–6.92 (9H, m, Ph), 5.01 (1H, d, J 11.5 Hz,
CHaHbPh), 4.84 (1H, d, J 11.6 Hz, CHaHbPh), 4.52 (1H, s, C4–H), 3.83
(3H, s, OCH3), 2.35 (3H, s, CH3S), 2.33 (3H, s, CH3S); dC (100 MHz,
CDCl3) 164.7, 156.4, 135.2, 128.8, 128.6, 128.2, 128.1, 127.5, 127.4,
118.3, 114.2, 69.6, 55.1, 44.4, 13.6, 12.3.