New methodology for the preparation of 3-hydroxy-2-pyridinone (3,2-HOPO) chelators—reaction of amines with a novel electrophilic 3,2-HOPO precursor

The preparation of the new electrophilic iminium ester mesylate salt 5 and its reaction with primary and secondary amines have been investigated. Aniline, t-butylamine, and secondary amines react with 5 via ring opening to give the corresponding HOPO derivatives in high yields. The usefulness of thi...

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Bibliographic Details
Published in:Tetrahedron letters 2002-10, Vol.43 (41), p.7379-7383
Main Authors: Lambert, Timothy N, Chittamuru, Sumathi, Jacobs, Hollie K, Gopalan, Aravamudan S
Format: Article
Language:English
Subjects:
hydroxypyridinones
iron overload diseases
metal ion chelators
MRI contrast agents
synthesis
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Summary:The preparation of the new electrophilic iminium ester mesylate salt 5 and its reaction with primary and secondary amines have been investigated. Aniline, t-butylamine, and secondary amines react with 5 via ring opening to give the corresponding HOPO derivatives in high yields. The usefulness of this methodology has been demonstrated by the preparation of two new di-HOPO derivatives 19 and 21 . This method allows the introduction of the HOPO ligand onto a variety of amine platforms without the concomitant formation of an amide bond and provides access to HOPO chelators of increased water solubility. The reactions of primary and secondary amines with the new electrophilic mesylate salt 5 have been investigated and found to be useful for the synthesis of a variety of HOPO derivatives.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01730-6