title: Preparation of bifunctional isocyanate hydroxamate linkers: Synthesis of carbamate and urea tethered polyhydroxamic acid chelators.
abstract: Two novel bifunctional N-methylhydroxamate-isocyanate linkers 20 and 21 were prepared in good yield and high purity from the corresponding amine salts using a biphasic reaction with phosgene. The facile ring opening reaction of N-Boc lactams using the anion of O-benzylhydroxylamine gave the protected amino hydroxamates 6a and 6c in good yields. The selective methylation of the hydroxamate nitrogen in the presence of the N-Boc group in these intermediates could be readily accomplished. The utility of the linkers was clearly demonstrated by the synthesis of the carbamate-tethered trishydroxamic acid 27 and the urea-tethered 29.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003-8001.
authors.forename: Rasika
authors.initials: R
authors.lastname: Fernando
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Shirley
authors.forename: Emilio
authors.initials: E
authors.lastname: Torres
authors.forename: Hollie K
authors.initials: HK
authors.lastname: Jacobs
authors.forename: Aravamudan S
authors.initials: AS
authors.lastname: Gopalan