New synthetic approach for acyclic and cyclic hydroxamic acids: Preparation of polyhydroxamate chelators for iron

ORGN 534

Aravamudan S. Gopalan, agopalan@nmsu.edu, Yuan Liu, yualiu@nmsu.edu, and Hollie K. Jacobs, hjacobs@nmsu.edu. Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003-8001
As part of a program for the design and synthesis of chelators for the specific binding of iron, we have been interested in developing methods for the preparation of a variety of hydroxamic acids including cyclic hydroxamic acids. The conventional method for the preparation of hydroxamic acids usually involves coupling of acyl derivatives with hydroxylamines. We have developed a new strategy for the preparation of a variety of hydroxamic acids that involves N-benzyloxycarbamic acid ethyl ester, I, as the key synthon. N-Alkylation of I occurs in excellent yields to give N-alkyl carbamates. A number of stabilized carbon nucleophiles react with I giving intermediates of type II. The intramolecular version of this reaction has been successfully used to prepare cyclic hydroxamic acids, III, a class of ligands whose coordination chemistry has not been well explored. The scope and limitations of this new methodology including applications to the preparation of polyhydroxamic acids will be discussed.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006