2932
A. Jarrahpour, M. Zarei / Tetrahedron 65 (2009) 2927–2934
(ArH, m, 15H); 13C NMR (62.9 MHz, CDCl3)
d
14.8 (Me), 61.1 (OCH2),
4.5.21. 1-(4-Ethoxyphenyl)-4-(4-nitrophenyl)-3-vinylazetidin-2-
one (8a)
White crystalline solid. Yield: (0.22 g, 64%), mp: 60–62 ꢀC; IR
(CHCl3) cmꢁ1: 1340, 1527 (NO2), 1739 (CO, -lactam); 1H NMR
(250 MHz, CDCl3)
63.7 (C-4), 81.2 (C-3), 109.0, 115.2, 118.0, 118.7, 123.6, 124.5, 126.7,
126.9,127.7,128.9,129.6,129.7,129.8,133.8,140.5,148.1,154.4,156.3
(aromatic carbons), 161.7 (CO,
Anal. Calcd for C27H22N2O5: C, 71.35; H, 4.88; N, 6.16. Found: C,
71.41; H, 4.92; N, 6.20.
b
-lactam); GC–MS m/z¼454 [Mþ].
b
d
1.24 (Me, t, 3H, J¼6.9), 3.63 (H-3, dd, 1H,
J¼2.5, 7.5), 3.84 (OCH2, q, 2H, J¼6.9), 4.84 (H-4, d, 1H, J¼2.5),
5.21–5.33 (vinilic H, m, 2H), 5.87–6.03 (vinilic H, m, 1H), 6.64–
4.5.17. 4-(4-Chlorophenyl)-1-(4-ethoxyphenyl)-3-(naphthalen-2-
yloxy)-azetidin-2-one (4q)
8.11 (ArH, m, 8H); 13C NMR (62.9 MHz, CDCl3)
d 14.7 (Me), 60.2
(OCH2), 63.6 (C-3), 64.0 (C-4), 115.0, 118.2, 121.6, 123.9, 126.8,
Light-yellow solid. Yield: (0.42 g, 95%), mp: 140–142 ꢀC; IR (KBr)
130.1, 140.0, 144.9, 147.9, 155.7 (C]C, aromatic carbons), 163.9
cmꢁ1: 1748 (CO,
b
-lactam); 1H NMR (250 MHz, CDCl3)
d
1.35 (Me, t,
(CO,
b
-lactam); GC–MS m/z¼338 [Mþ]. Anal. Calcd for
3H, J¼7.0), 3.90 (OCH2, q, 2H, J¼7.0), 5.35 (H-4, d, 1H, J¼4.5), 5.64
C19H18N2O4: C, 67.44; H, 5.36; N, 8.28. Found: C, 67.29; H, 5.40;
N, 8.19.
(H-3, d, 1H, J¼4.5), 6.67–8.08 (ArH, m, 15H); 13C NMR (62.9 MHz,
CDCl3)
d 14.9 (Me), 61.4 (OCH2), 64.6 (C-4), 81.0 (C-3), 109.1, 114.8,
115.1, 118.3, 118.9, 123.9, 124.3, 126.5, 126.9, 127.7, 128.7, 129.5, 130.9,
4.5.22. 4-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-vinylazetidin-
2-one (8b)
131.4, 133.9, 134.6, 154.7, 156.1 (aromatic carbons), 162.2 (CO, b-
lactam); GC–MS m/z¼445 [Mþ, 37Cl], 443 [Mþ, 35Cl]. Anal. Calcd for
C27H22ClNO3: C, 73.05; H, 5.00; N, 3.16. Found: C, 73.13; H, 5.09; N,
3.11.
White solid. Yield: (0.22 g, 71%), mp: 73–75 ꢀC; IR (CHCl3)
cmꢁ1: 1737 (CO, -lactam); 1H NMR (250 MHz, CDCl3)
b d 3.54 (H-
3, dd, 1H, J¼2.4, 7.9), 3.61 (OMe, s, 3H), 4.65 (H-4, d, 1H, J¼2.4),
5.16–5.27 (vinilic H, m, 2H), 5.84–5.90 (vinilic H, m, 1H), 6.63–
4.5.18. 1-(4-Methoxyphenyl)-3-(5-norbornene-2,3-
7.41 (ArH, m, 8H); 13C NMR (62.9 MHz, CDCl3)
d
55.4 (OMe), 60.5
dicarboxyloylimido)-4-(4-nitrophenyl)-azetidin-2-one (7a)
White solid. Yield: (0.36 g, 78%), mp: 235–237 ꢀC; IR (CHCl3)
(C-3), 64.0 (C-4), 113.9, 118.3, 121.7, 127.4, 129.3, 131.4, 134.3,
146.4, 147.5, 156.2 (C]C, aromatic carbons), 164.5 (CO,
b-lac-
cmꢁ1: 1337, 1525 (NO2), 1735, 1768. (CO, imide), 1778 (CO,
b
-lac-
tam); GC–MS m/z¼315 [Mþ, 37Cl], 313 [Mþ, 35Cl]. Anal. Calcd for
C18H16ClNO2: C, 68.90; H, 5.14; N, 4.46. Found: C, 68.96; H, 5.27;
N, 4.40.
tam); 1H NMR (250 MHz, CDCl3)
d
1.47, 1.67 (H-11, 2d, 2H, J¼8.8),
3.04 (H-5, d, 1H, J¼5.0), 3.13 (H-10, d, 1H, J¼5.1), 3.29–3.40 (H-6 and
H-9, m, 2H), 3.68 (OMe, s, 3H), 4.85 (H-4, d, 1H, J¼2.5), 5.15 (H-3, d,
1H, J¼2.5), 6.12–6.22 (H-7 and H-8, m, 2H), 6.69–8.13 (ArH, m, 8H);
4.5.23. 1,4-Bis(4-methoxyphenyl)-3-vinylazetidin-2-one (8c)
13C NMR (62.9 MHz, CDCl3)
d
44.7, 45.2 (C-5, C-10), 45.8, 46.2 (C-6,
White solid. Yield: (0.24 g, 77%), mp: 77–79 ꢀC; IR (CHCl3)
C-9), 52.1 (C-11), 55.4 (OMe), 59.1 (C-4), 62.5 (C-3), 114.5, 118.3,
cmꢁ1: 1741.6 (CO, -lactam); 1H NMR (250 MHz, CDCl3)
b d 3.66,
123.5, 126.9, 130.2, 134.0, 140.0, 147.9, 148.2, 156.7 (C]C, aromatic
3.70 (2OMe, 2s, 6H), 3.74 (H-3, dd, 1H, J¼2.5, 7.7), 4.75 (H-4, d,
carbons), 160.3 (CO,
b-lactam), 176.2, 176.4 (CO, imide); GC–MS
1H, J¼2.5), 5.24–5.37 (vinilic H, m, 2H), 5.94–6.08 (vinilic H, m,
m/z¼459 [Mþ]. Anal. Calcd for C25H21N3O6: C, 65.35; H, 4.61; N,
1H), 6.72–7.26 (ArH, m, 8H); 13C NMR (62.9 MHz, CDCl3)
d 55.2,
56.7 (2OMe), 62.9 (C-3), 63.8 (C-4), 114.1, 118.4, 121.7, 126.7,
9.15. Found: C, 65.27; H, 4.68; N, 9.06.
128.3, 130.8, 132.0, 135.1, 147.6, 156.3 (C]C, aromatic carbons),
4.5.19. 4-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-(5-
norbornene-2,3-dicarboxyloylimido)-azetidin-2-one (7b)
White crystalline solid. Yield: (0.37 g, 83%), mp: >245 ꢀC; IR
163.4 (CO,
b
-lactam); GC–MS m/z¼309 [Mþ]. Anal. Calcd for
C19H19NO3: C, 73.77; H, 6.19; N, 4.53. Found: C, 73.68; H, 6.11; N,
4.59.
(CHCl3) cmꢁ1: 1740, 1772 (CO, imide), 1781 (CO,
b
-lactam); 1H
NMR (250 MHz, CDCl3)
d
1.54, 1.75 (H-11, 2d, 2H, J¼8.8), 3.30
4.5.24. 10-Benzyl-1-(2,4-dimethoxyphenyl)-3-phenoxyspiro-
[azetidine-2,30-indoline]-20,4-dione (10a)
(H-5, d, 1H, J¼7.5), 3.35 (H-10, d, 1H, J¼7.5), 3.40–3.48 (H-6 and
H-9, m, 2H), 3.73 (OMe, s, 3H), 4.88 (H-4, d, 1H, J¼2.5), 5.05 (H-3,
d, 1H, J¼2.5), 6.17–6.25 (H-7 and H-8, m, 2H), 6.75–7.49 (ArH, m,
Light-yellow crystalline solid. Yield: (0.42 g, 83%), mp: 169–
171 ꢀC; IR (KBr) cmꢁ1: 1725 (CO, isatin), 1765 (CO, -lactam); 1H
b
8H); 13C NMR (62.9 MHz, CDCl3)
d
45.3, 45.8 (C-5, C-10), 47.1,
NMR (250 MHz, CDCl3)
benzyl, 2d, 2H, J¼14.8), 5.55 (H-3, s, 1H), 6.37–8.01 (ArH, m, 17H);
13C NMR (62.9 MHz, CDCl3)
43.8 (CH2-benzyl), 55.3, 56.0
d 3.30, 3.34 (2OMe, s, 6H), 4.78, 5.13 (CH2-
47.9 (C-6, C-9), 52.1 (C-11), 55.4 (OMe), 59.4 (C-4), 62.7 (C-3),
114.4, 118.9, 123.9, 127.3, 129.6, 132.7, 134.5, 142.4, 148.3, 155.3
d
(C]C, aromatic carbons), 161.7 (CO,
b
-lactam), 177.0, 177.3 (CO,
(2OMe), 68.1 (C-4), 84.8 (C-3), 101.2, 108.3, 113.2, 116.9, 122.6,
123.9, 124.0, 125.2, 126.9, 127.1, 128.4, 130.0, 130.9, 131.7, 135.0,
imide); GC–MS m/z¼450 [Mþ, 37Cl], 448 [Mþ, 35Cl]. Anal. Calcd
for C25H21ClN2O4: C, 66.89; H, 4.72; N, 6.24. Found: C, 66.95; H,
4.81; N, 6.30.
136.3, 141.9, 150.2, 151.5, 158.9 (aromatic carbons), 164.1 (CO, b-
lactam), 172.6 (CO, isatin); GC–MS m/z¼506 [Mþ]. Anal. Calcd for
C31H26N2O5: C, 73.50; H, 5.17; N, 5.53. Found: C, 73.43; H, 5.29; N,
5.50.
4.5.20. 1-(4-Ethoxyphenyl)-3-(5-norbornene-2,3-
dicarboxyloylimido)-4-(4-nitrophenyl)-azetidin-2-one (7c)
Light-yellow solid. Yield: (0.35 g, 75%), mp: 209–211 ꢀC; IR
4.5.25. 10-Benzyl-3-(2,4-dichlorophenoxy)-1-(2,4-dimeth-
oxyphenyl)spiro[azetidine-2,30-indoline]-20,4-dione (10b)
Light-yellow solid. Yield: (0.44 g, 76%), mp: 155–157 ꢀC; IR (KBr)
(CHCl3) cmꢁ1: 1341, 1533 (NO2), 1735, 1767 (CO, imide), 1776 (CO,
b-
lactam); 1H NMR (250 MHz, CDCl3)
d
1.41 (Me, t, 3H, J¼6.8), 1.57,
1.76 (H-11, 2d, 2H, J¼8.9), 3.13 (H-5, d, 1H, J¼5.4), 3.21 (H-10, d, 1H,
J¼5.2), 3.38–3.45 (H-6 and H-9, m, 2H), 3.98 (OCH2, q, 2H, J¼6.8),
4.93 (H-4, d, 1H, J¼2.5), 5.24 (H-3, d, 1H, J¼2.5), 6.21–6.30 (H-7 and
H-8, m, 2H), 6.76–8.22 (ArH, m, 8H); 13C NMR (62.9 MHz, CDCl3)
cmꢁ1: 1723 (CO, isatin), 1767 (CO, -lactam); 1H NMR (250 MHz,
b
CDCl3)
d 3.26, 3.32 (2OMe, s, 6H), 4.83, 5.19 (CH2-benzyl, 2d, 2H,
J¼15.0), 5.62 (H-3, s, 1H), 6.52–8.11 (ArH, m, 15H); 13C NMR
(62.9 MHz, CDCl3)
d 44.6 (CH2-benzyl), 54.7, 55.4 (2OMe), 67.9 (C-
d
14.2 (Me), 44.7, 44.9 (C-5, C-10), 45.8, 46.2 (C-6, C-9), 52.2 (C-11),
4), 82.1 (C-3), 107.0, 109.9, 115.2, 115.5, 123.8, 124.5, 124.8, 125.9,
127.6,127.8,128.8,129.9,130.4, 131.1,136.3,136.5, 143.2,151.2,152.4,
59.0 (OCH2), 62.4 (C-4), 63.7 (C-3), 115.0, 118.3, 123.5, 126.9, 129.8,
130.1, 134.5, 140.1, 143.7, 156.1 (C]C, aromatic carbons), 160.3 (CO,
b
Calcd for C26H23N3O6: C, 65.95; H, 4.90; N, 8.87. Found: C, 66.03; H,
4.97; N, 8.85.
159.3, 159.5, 160.2 (aromatic carbons), 163.5 (CO, b-lactam), 171.9
-lactam), 176.2, 176.5 (CO, imide); GC–MS m/z¼473 [Mþ]. Anal.
(CO, isatin); GC–MS m/z¼578 [Mþ, 37Cl], 574 [Mþ, 35Cl]. Anal. Calcd
for C31H24Cl2N2O5: C, 64.70; H, 4.20; N, 4.87. Found: C, 64.81; H,
4.33; N, 4.96.