986
M. Hosseini-Sarvari et al. / C. R. Chimie 15 (2012) 980–987
added. The reaction mixture was stirred for a certain
period of time (Tables 1 and 2) as required to complete the
reaction (monitored by TLC) at room temperature. The
reaction mixture was diluted with EtOAc and centrifuged
to remove the catalyst. Then the organic layer was washed
with aqueous solution of sodium bicarbonate and dried
over anhydrous sodium sulfate. Evaporation of solvent
furnished practically pure products. The identity of these
compounds was easily established by comparison of their
1H NMR spectra with those of authentic samples.
(OCH2), 80.5 (C-3), 115.0, 116.7, 117.0, 118.5, 118.8,
125,5, 128.7, 129.1, 129.8, 138.4, 155.2, 155.2, 159.5,
(aromatic carbon), 161.6 (CO Amidic), 162.3 (CO
b-
lactam); GC-MS m/z (%) = 436 (1.9) [M+], 368 (1.3), 273
(28.0), 245 (100.0), 211 (19.9), 135 (14.4), 106 (31.7);
analysis calculated for C24H21ClN2O4: C, 67.56; H, 5.16; N,
6.85. Found: C, 66.98; H, 5.10; N, 6.91%.
3.1.4. N-(4-(1-(4-Ethoxyphenyl)-3-(naphthalene-2-yloxy)-
4-oxoazetidin-2-yl)phenyl)formamide (2d)
White crystal purified by thin layer chromatography
(eluent: 4:1 CHCl3-EtOAc) (yield 71%, 0.32 g); Mp: 160–
3.1.1. N-(4-(1-(4-Ethoxyphenyl)-4-oxo-3-phenoxy-azetidin-
2-yl)phenyl)formamide (2a)
162 8C; IR (KBr, cmÀ1): 1679 (CO Amidic), 1740 (CO
b-
White powder purified by column chromatography
(eluent: 5:1 CHCl3-EtOAc) (yield 95%, 0.38 g); Mp: 148–
lactam), 3339 (NH); 1H NMR (250 MHz, DMSO-d6)
d 1.26
(3H, t, J 6.9 Hz, -CH3), 3.93 (2H, m, -OCH2), 5.70 (1H, d, J
5.0 Hz, H-4), 5.94 (1H, d, J 5.0 Hz, H-3), 6.89 (2H, d, J 8.9 Hz,
Ar-H), 6.95-7.04 (1H, m, Ar-H), 7.23 (2H, d, J 8.9 Hz, Ar-H),
7.30–7.47 (7H, m, Ar-H), 7.69 (1H, d, J 9.0 Hz, Ar-H), 7.75–
152 8C; IR (KBr, cmÀ1): 1749 (CO
b
-lactam), 1661 (CO
Amidic), 3339 (NH); 1H NMR (250 MHz, DMSO-d6)
d
1.26
(3H, t, J 7.5 Hz, -CH3), 3.93 (2H, q, J 7.5 Hz, -OCH2), 5.61 (1H,
d, J 5.0 Hz, H-4), 5.70 (1H, d, J 5.0 Hz, H-3), 6.78–6.89 (5H,
m, Ar-H), 7.01–7.13 (4H, m, Ar-H), 7.19 (2H, d, J 8.9 Hz, Ar-
H), 7.45 (2H, d, J 7.1 Hz, Ar-H), 8.16 (1H, s, CHO), 10.05 (1H,
7.79 (2H, m, Ar-H); 13C NMR (62.9 MHz, DMSO-d6)
d 14.5
(Me), 60.6 (OCH2), 63.2 (C-4), 80.5 (C-3), 108.6, 115.0,
116.9, 117.8, 118.5, 118.7, 124.1, 126.5, 127.5, 128.7, 128.8,
129.3, 130.0, 133.6, 138.1, 154.1, 155.2 (aromatic carbon),
s, NH); 13C NMR (62.9 MHz, DMSO-d6)
d 14.5 (Me), 60.7
(OCH2), 63.1 (C-4), 80.5 (C-3), 115.0, 117.0, 118.4, 118.8,
121.6, 128.1, 128.6, 129.2, 129.9, 138.3, 155.2, 156.4
159.5 (CO amidic), 161.9 (CO b-lactam); GC-MS m/z
(%) = 452 (14.4), [M+], 308 (12.5), 289 (100.0), 268 (32.1),
239 (19.5), 144 (28.7), 106 (13.8), 83 (20.2), 57 (45.5);
analysis calculated for C28H24N2O4: C, 74.32; H, 5.35; N,
6.19. Found: C, 71.98; H, 5.21; N, 6.48%.
(aromatic carbon), 159.3 (CO-Amidic), 162.1 (CO
b-
lactam); GC-MS m/z(%) = 402 (1.7) [M+], 388 (4.7), 295
(3.2), 267 (1.8), 239 (100.0), 211 (19.5), 134 (14.2), 106
(23.0), 77 (11.2); analysis calculated for C24H22N2O4: C,
71.63; H, 5.51; N, 6.96. Found: C, 71.59; H, 5.49; N, 6.96%.
3.1.5. N-(3-(1-(4-Methoxyphenyl)-3-(naphthalene-2-
yloxy)-4-oxoazetidin-2-yl)phenyl)formamide (2e)
3.1.2. N-(4-(3-(2,4-Dichlorophenoxy)-1-(4-
White crystal purified by thin layer chromatography
(eluent: 4:1 CHCl3-EtOAc) (yield 83%, 0.36 g); Mp: 152–
methoxyphenyl)-4-oxoazetidin-2-yl)phenyl)formamide (2b)
White crystal purified by thin layer chromatography
(eluent: 4:1 CHCl3-EtOAc) (yield 75%, 0.31 g); Mp: 120–
123 8C; IR (KBr, cmÀ1): 1679 (CO Amidic), 1740 (CO
lactam), 3358 (NH); 1H NMR (250 MHz, DMSO-d6)
154 8C; IR (KBr, cmÀ1): 1689 (CO Amidic), 1751 (CO
b-
d 3.68
lactam), 3278 (NH); 1H NMR (250 MHz, DMSO-d6)
b
3.67
-
(3H, s, -OMe), 5.75 (1H, d, J 4.7 Hz, H-4), 5.97 (1H, d, J
4.7 Hz, H-3), 6.91 (2H, d, J 9.0 Hz, Ar-H), 7.14–7.44 (10H, m,
Ar-H), 7.62–7.77 (3H, m, Ar-H), 8.15 (1H, s, CHO), 10.14
d
(3H, s, OMe), 5.64 (1H, d, J 5.0 Hz, H-4), 5.84 (1H, d, J 5.0 Hz,
H-3), 6.82 (2H, d, J 10.3 Hz, Ar-H), 6.91 (2H, d, J 7.5 Hz, Ar-
H), 7.06 (2H, d, J 9.0 Hz, Ar-H), 7.16–7.25 (4H, m, Ar-H),
7.49–7.54 (2H, m, Ar-H), 8.17 (1H, s, CHO), 10.09 (1H, s, -
(1H, s, NH); 13C NMR(62.9 MHz, DMSO-d6)
d (ppm); 60.5
(OMe), 66.6 (C-4), 85.8 (C-3), 114.2, 117.2, 119.3, 119.7,
121.2, 123.2, 123.7, 129.3, 131.7, 132.0, 132.7, 133.8, 134.1,
134.5, 135.5, 138.9, 153.6, 159.7, 161.1 (aromatic carbon),
NH); 13C NMR (62.9 MHz, DMSO-d6)
d 55.2 (OMe), 60.6 (C-
4), 80.5 (C-3), 114.5, 116.8, 118.2, 118.4, 119.1, 123.5,
125.5, 128.7, 129.0, 129.9, 133.8, 138.1, 155.2, 156.0, 159.5,
162.2 (CO Amidic), 167.3 (CO b-lactam); GC-MS m/z
(%) = 438 (43.6) [M+], 410 (12.7), 368 (17.1), 289 (54.8), 254
(86.9), 226 (30.6), 144 (28.5), 111 (18.5), 83 (45.2), 57
(100.0); analysis calculated for C27H22N2O4: C, 73.96; H,
5.06; N, 6.39. Found: C, 71.96; H, 5.20; N, 6.73%.
161.6 (aromatic carbon), 162.3 (CO b-lactam); GC-MS m/z
(%) = 422 (10.1) [M+], 258 (2.9), 169 (4.1), 139 (4.5), 111
(14.8), 83 (29.7), 57 (100.0); analysis calculated for
C23H19ClN2O4: C, 65.33; H, 4.53; N, 6.62. Found: C,
60.61; H, 4.44; N, 6.48%.
3.1.6. N-(3-(1-(4-Methoxyphenyl)-4-oxo-3-phenoxy-
azetidin-2-yl)phenyl)formamide (2f)
3.1.3. N-(4-(3-(4-Chlorophenoxy)-1-(4-ethoxyphenyl)-4-
oxoazetidin-2-yl)phenyl)formamide (2c)
White crystal purified by thin layer chromatography
(eluent: 4:1 CHCl3-EtOAc) (yield 95%, 0.36 g); Mp: 160–
White crystal purified by thin layer chromatography
(eluent: 4:1 CHCl3-EtOAc) (yield 80%, 0.34 g); Mp: 158–
1638C; IR (KBr, cmÀ1): 1684 (CO Amidic), 1749 (CO
b-
lactam), 3339 (NH); 1H NMR (250 MHz, DMSO-d6)
d 3.67
160 8C; IR (KBr, cmÀ1): 1665 (CO Amidi), 1749 (CO
b-
(3H, s, -OMe), 5.65 (1H, d, J 5.0 Hz, H-4), 5.83 (1H, d, J
5.0 Hz, H-3), 6.80 (2H, d, J 7.8 Hz, Ar-H), 6.91 (3H, d, J 9.0 Hz,
Ar-H), 7.14–7.25 (6H, m, Ar-H), 7.49–7.55 (2H, m, Ar-H),
8.16 (1H, s, CHO), 10.16 (1H, s, NH); 13C NMR (62.9 MHz,
lactam), 3302 (NH); 1H NMR (250 MHz, DMSO-d6)
d 1.02
(3H, t, J 5.0 Hz, -CH3), 3.92 (2H, q, J 6.8 Hz, -OCH2), 5.60
(1H, d, J 5.0 Hz, H-4), 5.80 (1H, d, J 5.0 Hz, H-3), 6.81–6.89
(4H, m, Ar-H), 7.07 (2H, d, J 7.5 Hz, Ar-H), 7.18–7.22 (2H, m,
Ar-H), 7.30 (2H, d, J 7.5 Hz, Ar-H), 7.60 (2H, d, J 8.4 Hz, Ar-
H), 8.26 (1H, s, CHO), 10.15 (1H, s, NH); 13C NMR
DMSO-d6)
d 55.2 (OMe), 61.3 (C-4), 80.6 (C-3), 112.8,
114.0, 114.5, 115.3, 116.0, 118.3, 121.7, 128.6, 129.3, 130.3,
133.7, 148.4, 155.8, 156.4 (aromatic carbon), 159.48 (CO
(62.9 MHz, DMSO-d6)
d
14.5 (CH3), 60.4 (C-4), 63.1
Amidic), 162.08 (CO b-lactam); GC-MS m/z (%) = 388 (7.3)