Journal
TETRAHEDRON LETTERS
Volume 54, Issue 7, Pages 630-634Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.11.136
Keywords
Aza-Michael reaction; Hydroxypyridinone; Metal ion chelators; Vinyl sulfonamide; Rate acceleration in water
Categories
Funding
- NIH [S06 GM08136, 1SC3GM084809]
- NIH-RISE [GM61222]
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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. (c) 2012 Elsevier Ltd. All rights reserved.
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