Synthesis of Some Biologically Important 3-Oxacepham Derivatives

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Title Synthesis of Some Biologically Important 3-Oxacepham Derivatives
 
Creator Mohammad Rafiqul Islam; Department of Applied Chemistry & Chemical Technology, University of Dhaka, Dhaka-1000
Mohammad Nurnabi; Department of Applied Chemistry & Chemical Technology, University of Dhaka, Dhaka-1000
AM Sarwaruddin Chowdhury; Department of Applied Chemistry & Chemical Technology, University of Dhaka, Dhaka-1000
Mohammad Mehdi Masud; Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka-1000
 
Subject Pharmacy
Azetedinone; β-lactam; oxacepham; cycloaddition; imine; ketene; oxathiazine
 
Description The 6H-oxathiazines 1a-e having imine moiety underwent [2+2] cycloaddition with phenoxyacetylchloride in the presence of Et3N to give β-lactam derivatives 2a-e in high yield. The X-ray crystallographic analysis revealed the relative stereochemistry that the substituents at C-2 and C-4 were cis configurated. The subtituents at C-6 and C-7 were also cis to each other. However, the 6H-oxathiazines 1f-i containing tert-butyl or methyl group at C-4 did not undergo the cycloaddition. Key words: Azetedinone, β-lactam, oxacepham, cycloaddition, imine, ketene, oxathiazine. Dhaka Univ. J. Pharm. Sci. Vol.5(1-2) 2006 The full text is of this article is available at the Dhaka Univ. J. Pharm. Sci. website
 
Publisher Dhaka University
 
Date 2007-06-20
 
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Format application/pdf
 
Identifier http://www.banglajol.info/index.php/JPharma/article/view/228
 
Source Dhaka University Journal of Pharmaceutical Sciences; Vol 5, No 1 (2006); 47-51
 
Language en