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1,3-Dipolar cycloaddition reactions of pyrazolidinium ylides with vinyl sulfones. A regioselective synthesis of bicyclic pyrazolidinone antibacterial agents

✍ Scribed by Louis N. Jungheim; Charles J. Barnett; Joseph E. Gray; Linus H. Horcher; Timothy A. Shepherd; Sandra K. Sigmund

Book ID
104203585
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
947 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

The 1,3-dipolar cyclosddition reaction of pyrazolidinium ylide 1 vith substituted vinyl sulfones 5 warn studied. Elimination of benzeneaulfinic acid from the resulting cycloadducts gave rise to bicyclic pyrazolidiaones 3. The (E)-olefin isomers vere found to undergo cycloadditioo in a highly regioselective fashion. These pyrazolidinones 2 represent the nuclei of an exciting nev class of potent antibacterial agents that mimic B-lactaar. L. N. Jmcmm et al.

Table I. Cycloaddition of Ylide 1 with Propiolete Esters 2'.

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