118 New Approach for the Synthesis of Primary and Secondary Hydroxamic Acids Using Olefin Cross Metathesis Reactions

Wednesday, November 4, 2009: 10:40 AM
Rio Grande (Camino Real Hotel)
Priya Pisipati , Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM
Hollie K. Jacobs , Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM
Aravamudan S. Gopalan , Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM
The synthesis of hydroxamic acids is of interest due to their biomedical applications, which include treatment of iron overload diseases as well as anti-cancer and anti-bacterial properties. The conventional method for the synthesis of hydroxamic acids involves coupling of acyl derivatives with hydroxylamines. While this approach is very useful, it can be limited by the availability of the acid and hydroxylamine components and presents a challenge in the preparation of polyhydroxamic acids. Here, we report a new strategy for preparation of hydroxamic acids directly from readily available alkenes using an olefin cross metathesis reaction as the key step. A number of N-alkoxyacrylamides were prepared and their cross coupling reactions with various olefins using Grubbs catalyst were examined. In general, the reaction proceeded in good yields to give the desired unsaturated amide intermediates for accessing hydroxamic acids. The application of this new methodology towards the synthesis of various target molecules having therapeutic applications will also be discussed.
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