The Open Organic Chemistry Journal
2009, 3 : 35-41Published online 2009 April 3. DOI: 10.2174/1874095200903010035
Publisher ID: TOOCJ-3-35
Smiles Rearrangement in the Synthesis of Di- and Triiodinated 5- (Acylamino)-1,3-Benzenedicarboxamides
Centro Ricerche Bracco, Bracco Imaging spa, via Ribes 5, 10010 Colleretto Giacosa (TO), Italy
ABSTRACT
Both the number and the position of iodine atoms on the aromatic ring of polyiodinated N,N’-bis(2,3- dihydroxypropyl)-5-[2-methylamino-2-oxoethoxy]-1,3-benzenedicarboxamides are crucial to define the structure of the product obtained by treatment with aqueous NaOH. The 2,6-diiodo and the 2,4,6-triiodo derivatives give the corresponding Smiles rearrangement products in 77 and 96% yields, respectively. Conversely, under the same conditions, the 2,4- diiodo isomer predominantly undergoes hydrolysis of the phenoxyacetamide moiety.