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New Journal of Chemistry
Page 8 of 11
DOI: 10.1039/C9NJ02759A
ARTICLE
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Fe3O4 nanoparticles (0.025 mmol) were added to a solution of 1: 1752 (CO, β‐lactam), 3296, 3397 (NH2); H NMR (300 MHz,
β‐lactams (0.25 mmol) and sodium hydroxide (0.25 mmol) in 5 CDCl3): δ 3.40 (OMe, s, 3H), 3.60 (NH2, s, 2H), 5.02 (H‐4, d, 1H, J
mL of ethanol 95% and the mixture was stirred on oil‐bath at = 4.89), 5.34 (H‐3, d, 1H, J = 4.89), 6.77‐7.24 (ArH, m, 8H); 13C
o
80 C. The progress of reactions was monitored by thin layer NMR (75 MHz): δ 57.9 (OMe), 63.78 (C‐4), 82.2 (C‐3), 117.0,
chromatography. After completion and cooling of reaction, the 120.6, 126.3, 128.3, 128.5, 133.0, 133.8, 147.7 (aromatic
catalyst was separated using magnetic separation. Then H2O (5 carbons), 164.2 (CO, β‐lactam). Anal. Calcd for C16H15ClN2O2: C,
mL) was added and the mixture extracted with CHCl3 (10 mL). 63.48; H, 4.99; N, 9.25. Found: C, 63.63; H, 5.17; N, 9.32.
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The organic layer was washed with 10% aqueous NaHCO3 (10 1‐(4‐Aminophenyl)‐3‐phenoxy‐4‐styrylazetidin‐2‐one
(5j):
mL) and brine (20 mL), and then dried over Na2SO4. After Yield: 88%. White solid. m.p: 197‐199oC. IR (KBr) cm‐1: 1759
filtration and evaporation of the solvent, the crude residue (CO, β‐lactam), 3341, 3426 (NH2); 1H NMR (300 MHz, CDCl3): δ
was purified by recrystallization from ethyl acetate to give 3.55 (NH2, s, 2H), 4.73 (H‐4, dd, 1H, J = 4.59, 8.61), 5.27 (H‐3, d,
pure products 5a‐p. Characterization data for 5a‐b, 5d and 5f 1H, J = 4.59), 6.11 (H‐5, dd, 1H, J = 8.61, 15.99), 6.59‐7.38
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have been previously reported.44
(CH=CH and ArH, m, 15H); 13C NMR (75 MHz): δ 57.2 (C‐4),
82.4 (C‐3), 116.1, 116.9, 119.3, 122.7, 125.2, 127.1, 127.7,
128.6, 129.4, 129.9, 134.5, 137.1, 147.1, 157.6 (C=C, aromatic
carbons), 162.4 (CO, β‐lactam). Anal. Calcd for C23H20N2O2: C,
77.51; H, 5.66; N, 7.86. Found: C, 77.67; H, 5.81; N, 7.96.
4‐(4‐Aminophenyl)‐3‐methoxy‐1‐(4‐methoxyphenyl)azetidin‐
2‐one (5c): Yield: 62%. White solid. m.p: 153‐155 C. IR (KBr)
o
cm‐1: 1736 (CO, β‐lactam), 3361, 3446 (NH2); 1H NMR (300
MHz, CDCl3): δ 3.41, 3.85 (2 OMe, 2s, 6H), 3.61 (NH2, s, 2H),
5.04 (H‐4, d, 1H, J = 4.70), 5.24 (H‐3, d, 1H, J = 4.70), 6.60‐7.17
(ArH, m, 8H); 13C NMR (75 MHz): δ 55.8, 63.1 (2 OMe), 63.1 (C‐
4), 79.6 (C‐3), 113.6, 115.5, 120.7, 121.8, 128.1, 130.6, 144.4,
157.1 (aromatic carbons), 163.9 (CO, β‐lactam). Anal. Calcd for
C17H18N2O3: C, 68.44; H, 6.08; N, 9.39. Found: C, 68.54; H, 6.22;
N, 9.33.
3‐(4‐Aminophenoxy)‐1,4‐diphenylazetidin‐2‐one (5k): Yield:
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93%. White solid. m.p: 187‐190 C. IR (KBr) cm‐1: 1760 (CO, β‐
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lactam), 3373, 3424 (NH2); H NMR (300 MHz, CDCl3): δ 3.59
(NH2, s, 2H), 5.33 (H‐4, d, 1H, J = 4.80), 5.69 (H‐3, d, 1H, J =
4.80), 6.52‐7.35 (ArH, m, 14H); 13C NMR (75 MHz): δ 62.7 (C‐4),
80.9 (C‐3), 114.0, 118.7, 119.8, 126.1, 126.6, 128.4, 128.9,
134.6, 138.0, 144.1, 149.5, 153.2 (aromatic carbons), 161.6
(CO, β‐lactam). Anal. Calcd for C21H18N2O2: C, 76.34; H, 5.49; N,
8.48. Found: C, 76.49; H, 5.66; N, 8.60.
4‐(4‐Aminophenyl)‐1‐(4‐methoxyphenyl)‐3‐(naphthalen‐2‐
yloxy)azetidin‐2‐one (5e): Yield: 88%. White solid. m.p: 177‐
180 oC. IR (KBr) cm‐1: 1763 (CO, β‐lactam), 3382, 3429 (NH2); 1H
NMR (300 MHz, CDCl3): δ 3.57 (NH2, s, 2H), 3.72 (OMe, s, 3H),
5.29 (H‐4, d, 1H, J = 4.50), 5.68 (H‐3, d, 1H, J = 4.50), 6.52‐7.57
(ArH, m, 15H); 13C NMR (75 MHz): δ 56.3 (OMe), 62.8 (C‐4),
81.1 (C‐3), 111.6, 114.4, 115.5, 118.3, 120.7, 121.7, 123.9,
127.2, 127.3, 128.1, 128.7, 129.2, 130.6, 131.1, 135.1, 144.4,
156.3, 156.7 (aromatic carbons), 163.6 (CO, β‐lactam). Anal.
Calcd for C26H22N2O3: C, 76.08; H, 5.40; N, 6.82. Found: C,
76.26; H, 5.57; N, 7.01.
3‐(4‐Aminophenoxy)‐4‐(4‐chlorophenyl)‐1‐phenylazetidin‐2‐
one (5l): Yield: 92%. White solid. m.p: 178‐180 oC. IR (KBr) cm‐
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1: 1758 (CO, β‐lactam), 3380, 3421 (NH2); H NMR (300 MHz,
CDCl3): δ 3.43 (NH2, s, 2H), 5.29 (H‐4, d, 1H, J = 4.41), 5.72 (H‐3,
d, 1H, J = 4.41), 6.5‐7.34 (ArH, m, 13H); 13C NMR (75 MHz): δ
64.6 (C‐4), 84.0 (C‐3), 112.4, 114.4, 117.9, 120.5, 126.6, 127.9,
129.0, 134.1, 137.9, 144.7, 149.5, 154.1 (aromatic carbons),
162.9 (CO, β‐lactam). Anal. Calcd for C21H17ClN2O2: C, 69.14; H,
4.70; N, 7.68. Found: C, 69.28; H, 4.81; N, 7.77.
1‐(3‐Aminophenyl)‐4‐(4‐chlorophenyl)‐3‐phenoxyazetidin‐2‐
3‐(4‐Aminophenoxy)‐4‐(4‐chlorophenyl)‐1‐(4‐
one (5g): Yield: 84%. White solid. m.p: 160‐163 oC. IR (KBr) cm‐
methoxyphenyl)azetidin‐2‐one (5m): Yield: 89%. White solid.
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1: 1753 (CO, β‐lactam), 3381, 3419 (NH2); H NMR (300 MHz,
m.p: 212‐215 oC. IR (KBr) cm‐1: 1753 (CO, β‐lactam), 3387, 3445
CDCl3): δ 3.51 (NH2, s, 2H), 5.25 (H‐4, d, 1H, J = 4.70), 5.70 (H‐3,
d, 1H, J = 4.59), 6.54‐7.47 (ArH, m, 13H); 13C NMR (75 MHz): δ
63.2 (C‐4), 82.9 (C‐3), 105.5, 111.2, 116.5, 117.3, 122.5, 127.9,
128.6, 129.9, 132.9, 133.7, 139.2, 143.9, 151.3, 156.5
(aromatic carbons), 162.7 (CO, β‐lactam). Anal. Calcd for
C21H17ClN2O2: C, 69.14; H, 4.70; N, 7.68. Found: C, 69.30; H,
4.88; N, 7.76.
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(NH2); H NMR (300 MHz, CDCl3): δ 3.49 (NH2, s, 2H), 3.65
(OMe, s, 3H), 5.37 (H‐4, d, 1H, J = 4.71), 5.73 (H‐3, d, 1H, J =
4.71), 6.67‐7.31 (ArH, m, 12H); 13C NMR (75 MHz): δ 55.8
(OMe), 62.8 (C‐4), 82.4 (C‐3), 114.4, 114.8, 118.5, 121.1, 127.9,
128.5, 131.0, 133.4, 138.5, 144.7, 148.9, 155.9 (aromatic
carbons), 163.1 (CO, β‐lactam). Anal. Calcd for C22H19ClN2O3: C,
66.92; H, 4.85; N, 7.09. Found: C, 67.11; H, 5.02; N, 7.21.
1‐(4‐Aminophenyl)‐4‐(4‐chlorophenyl)‐3‐(2,4‐
3‐(4‐Aminophenoxy)‐4‐(4‐methoxyphenyl)‐1‐(p‐tolyl)azetidin‐
dichlorophenoxy)azetidin‐2‐one (5h): Yield: 85%. White solid.
m.p: 167‐170 oC. IR (KBr) cm‐1: 1756 (CO, β‐lactam), 3384, 3448
(NH2); 1H NMR (300 MHz, CDCl3): δ 3.39 (NH2, s, 2H), 5.20 (H‐4,
d, 1H, J = 5.01), 5.49 (H‐3, d, 1H, J = 5.01), 6.71‐7.38 (ArH, m,
11H); 13C NMR (75 MHz): δ 63.2 (C‐4), 81.3 (C‐3), 117.1, 119.6,
120.5, 126.6, 126.9, 128.3, 128.4, 128.8, 129.0, 132.9, 141.8,
145.9, 152.0, 156.5 (aromatic carbons), 163.3 (CO, β‐lactam).
Anal. Calcd for C21H15Cl3N2O2: C, 58.16; H, 3.49; N, 6.46. Found:
C, 58.29; H, 3.64; N, 6.58.
2‐one (5n): Yield: 95%. White solid. m.p: 175‐177 oC. . IR (KBr)
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cm‐1: 1739 (CO, β‐lactam), 3260 , 3392 (NH2); H NMR (300
MHz, CDCl3): δ 2.29 (Me, s, 3H), 3.45 (NH2, s, 2H), 3.68 (OMe, s,
3H), 5.18 (H‐4, d, 1H, J = 4.95), 5.68 (H‐3, d, 1H, J = 4.95), 6.58‐
7.27 (ArH, m, 12H); 13C NMR (75 MHz): δ 20.6 (Me), 55.9
(OMe), 62.8 (C‐4), 83.5 (C‐3), 113.3, 114.6, 118.7, 124.9, 125.7,
127.2, 131.4, 133.8, 135.9, 144.7, 151.2, 158.0 (aromatic
carbons), 162.3 (CO, β‐lactam). Anal. Calcd for C23H22N2O3: C,
73.78; H, 5.92; N, 7.48. Found: C, 73.89; H, 6.10; N, 7.57.
1‐(4‐Aminophenyl)‐4‐(4‐chlorophenyl)‐3‐methoxyazetidin‐2‐
1,4‐Bis(4‐aminophenyl)‐3‐phenoxyazetidin‐2‐one (5o): Yield:
one (5i): Yield: 65%. White solid. m.p: 158‐160 oC. IR (KBr) cm‐
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91%. Light‐yellow solid. m.p: 190‐192 C. IR (KBr) cm‐1: 1754
8 | J. Name., 2012, 00, 1‐3
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