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The authors thank the Shiraz University Research Council for
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31. General procedure:
A mixture of N,N-dimethylformamide (1.7 mmol) and
Me2SO4 or Et2SO4 (1.5 mmol) was stirred at 60–80 °C for 2 h. [In the case of
DMF/Me2SO4 by removal of excess DMF and addition of 2 ml of CHCl3: IR cmÀ1
1246, 1068 (C–O–C) and 1721 (C@N)]. After cooling to room temperature, the
resulting solution was added to a mixture of imine (1.0 mmol) and substituted
acetic acid (1.5 mmol) in dry dichloromethane. The reaction mixture was
stirred for 10–15 min, and then dry triethylamine (5.0 mmol) was added at
0 °C or at room temperature and the reaction mixture was stirred overnight at
room temperature. The solution was washed successively with 10% HCl
(20 ml), saturated NaHCO3 (20 ml) and brine (20 ml), dried over Na2SO4 and
then filtered. The solvent was evaporated under reduced pressure to give the
crude product. b-Lactams 2a–h, 2k–l were purified by crystallization from
ethyl acetate and b-lactams 2i–j by short column chromatography. 2-(1-(4-
Ethoxyphenyl)-2-oxo-4-styryl-azetidin-3-yl)isoindoline-1,3-dione (2g). Yield: 90%
mp: 160–162 °C; IR (CHCl3) cmÀ1: 1726, 1756 (CO, phth), 1778 (CO, b-lactam);
1H NMR (250 MHz, CDCl3) d 1.37 (Me, t, 3H, J = 6.9), 3.97 (OCH2, q, 2H, J = 6.8),
5.03 (H-4, dd, 1H, J = 5.5, 8.5), 5.68 (H-3, d, 1H, J = 5.5), 6.32 (H-5, dd, 1H, J = 8.5,
16.0), 6.85 (H-6, d, 1H, J = 16.0), 7.19–7.82 (ArH, m, 13H); 13C NMR (62.9 MHz,
CDCl3) d 14.8 (Me), 57.7 (OCH2), 61.0 (C-4), 63.7 (C-3), 115.0–155.8 (C@C,
aromatic carbons), 160.6 (CO, phth), 167.3 (CO, b-lactam); GC–MS m/z = 438
[M+]; Anal. Calcd for C27H22N2O4: C, 73.96; H, 5.06; N, 6.39. Found: C, 74.02; H,
5.09; N, 6.33.
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