| 3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: Aza-Michael addition reactions and the preparation of poly-HOPO chelators. | |
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MedLine Citation:
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PMID: 23355751 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The HOPO vinyl sulfonamide 3 and the corresponding HOPO acrylamide 10, were easily prepared by short synthetic sequences. Investigation of the aza-Michael reactions of these linkers showed that they proceed at a higher rate in solvent systems containing water. The scope and limits of the aza-Michael reactions of 3 and 10 were examined. Reagents 3 and 10 reacted cleanly with piperazine to give the corresponding adducts which were deprotected to give the di-HOPO ligands 7 and 16. Reaction of HOPO acrylamide 10 with 1,4,7-triazacyclononane gave the tris-adduct 17 which was deprotected to give the desired tris-HOPO ligand 18. Overall, the aza-Michael reactions of 3 and 10 appear to be governed not only by the solvent but also by the nature of the amine and the solubility of the reaction intermediates. |
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Authors:
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Gloria Martinez; Jayanthi Arumugam; Hollie K Jacobs; Aravamudan S Gopalan |
Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: Tetrahedron letters Volume: 54 ISSN: 0040-4039 ISO Abbreviation: Tetrahedron Lett. Publication Date: 2013 Feb |
Date Detail:
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Created Date: 2013-1-28 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2984819R Medline TA: Tetrahedron Lett Country: - |
Other Details:
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Languages: ENG Pagination: 630-634 Citation Subset: - |
Affiliation:
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Department of Chemistry and Biochemistry, MSC 3C, New Mexico State University, Las Cruces, NM 88003-8001 USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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