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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 6
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Original Articles

The Reaction of Hydrazine with α‐Cyanocinnamate Esters: A Caveat

Paul J. Erdman Department of Chemistry, University of Wisconsin—Eau Claire, Eau Claire, Wisconsin, 54702‐4004, USA
,
Jimmy L. Gosse Department of Chemistry, University of Wisconsin—Eau Claire, Eau Claire, Wisconsin, 54702‐4004, USA
,
Jamey A. Jacobson Department of Chemistry, University of Wisconsin—Eau Claire, Eau Claire, Wisconsin, 54702‐4004, USA
&
David E. Lewis Department of Chemistry, University of Wisconsin—Eau Claire, Eau Claire, Wisconsin, 54702‐4004, USACorrespondence[email protected]
Pages 1163-1171 | Received 16 Oct 2003, Published online: 21 Aug 2006
 
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Abstract

α‐Cyanocinnamate esters react with hydrazine to give initial products of conjugate addition that then undergo a fragmentation to give the azine of the carbonyl precursor to the starting ester, rather than intramolecular aminolysis to give the pyrazolidinone.

Acknowledgments

The financial support of the National Institutes of Health (Grant #1 R15 DA013578‐01), and the University of Wisconsin – Eau Claire Office of Research and Sponsored Programs is gratefully acknowledged.

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