February 2013 Zeolite-Supported One-Pot Synthesis of Bis-azetidinones Under Microwave Irradiation
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1,1′-(4,4′-(1,4-Phenylenebis(azanediyl))bis(4,1-phenylene))
bis(3-chloro-4-(4-nitrophenyl)azetidin-2-one) (3i). IR (KBr,
cmÀ1): 1764 (C═O b-lactam), 1336 (CN); 1H-NMR: d = 4.3 (s,
2H, –N–CH), 10.66 (br s, 2H, NH–Ar); 5.44 (d, 2H, CH–Cl);
6.6–7.5 (m, 20H, Ar–CH); 13C-NMR:
d 155.9 (cyclic,
>C═O), 59.9 (>CH–N<), 60.3 (>CH–Cl), 120.1–152.8
(Ar–C); mass spectra, (C36H26Cl2N6O6): m/z = 708. Elemental
analysis: Calcd (found): C, 60.94 (60.89); H, 3.69 (3.66); N,
11.84 (11.79).
1,1′-(4,4′-(1,4-Phenylenebis(azanediyl))bis(4,1-phenylene))
bis(3-chloro-4-(3-nitrophenyl)azetidin-2-one) (3j). IR (KBr,
1
cmÀ1): 1759 (C═O b-lactam), 1365 (CN); H-NMR: d = 4.2 (s,
2H, –N–CH), 10.59 (br s, 2H, NH); 5.44 (d, 2H, CH–Cl);
6.7–7.7 (m, 20H, Ar–CH); 13C-NMR: d 158.4 (cyclic, >C═O),
61.4 (>CH–N<), 63.5 (>CH–Cl), 117.8–157.3 (Ar–C); mass
spectra, (C36H26Cl2N6O6): m/z = 708. Elemental analysis: Calcd
(found): C, 60.94 (60.91); H, 3.69 (3.66); N, 11.84 (11.80).
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CONCLUSION
In conclusion, we have developed a general and highly
efficient method for the synthesis of a series of differently
substituted bis-2-azetidinones that were prepared via
Staudinger cycloaddition reaction in the presence of zeolite
catalyst under MW irradiation. The controlled MW heating
under sealed vessel conditions has shown several advantages
including fast, highly efficient, and environmentally friendly
solvent-free procedure that reduces reaction time, increases
product yield, and enhances product purity compared with
conventional synthetic methods. Several compounds could
be identified as the most biologically active members in com-
parison with the ampicillin drug. By this study, the titled bis-2-
azetidinones represent a class that needs further investigation
with the hope of finding new antimicrobial agents.
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Acknowledgment. We greatly acknowledge the Head of the
Chemistry Department, Rashtrasant Tukadoji Maharaj Nagpur
University, for laboratory facilities.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet