Document Detail


3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: Aza-Michael addition reactions and the preparation of poly-HOPO chelators.
MedLine Citation:
PMID:  23355751     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Gloria Martinez; Jayanthi Arumugam; Hollie K Jacobs; Aravamudan S Gopalan
Publication Detail:
Type:  JOURNAL ARTICLE    
Journal Detail:
Title:  Tetrahedron letters     Volume:  54     ISSN:  0040-4039     ISO Abbreviation:  Tetrahedron Lett.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-1-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2984819R     Medline TA:  Tetrahedron Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  630-634     Citation Subset:  -    
Affiliation:
Department of Chemistry and Biochemistry, MSC 3C, New Mexico State University, Las Cruces, NM 88003-8001 USA.
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