Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents

doi:10.3390/11010049

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Molecules 2006, 11(1), 49-58; doi:10.3390/11010049

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Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents

Aliasghar Jarrahpour* and Maaroof Zarei

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran

* Author to whom correspondence should be addressed.

Received: 9 March 2005; in revised form: 12 December 2005 / Accepted: 14 December 2005 / Published: 31 January 2006

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Abstract: New cis monocyclic β-lactams were synthesized by [2+2] Staudinger cycloaddition reactions of the imine (3,4-dimethoxybenzylidene)-(4-methoxyphenyl)- amine and ketenes derived from different acyl chlorides and Et3N. These monocyclic β-lactams were then cleaved by ceric ammonium nitrate (CAN) to give NH-monocyclic β-lactams, which in turn were converted to N-sulfonyl monocyclic β-lactams by treatment with four different sulfonyl chlorides in the presence of Et3N and 4,4-dimethyl- aminopyridine (DMAP).

Keywords: 2-Azetidinones; N-Sulfonyl β-lactams; Ketene; Imine; CAN; DMAP

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MDPI and ACS Style

Jarrahpour, A.; Zarei, M. Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents. Molecules 2006, 11, 49-58.

AMA Style

Jarrahpour A, Zarei M. Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents. Molecules. 2006; 11(1):49-58.

Chicago/Turabian Style

Jarrahpour, Aliasghar; Zarei, Maaroof. 2006. "Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents." Molecules 11, no. 1: 49-58.

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