Abstract
The synthesis of 2,4,6-triiodoisophthalamides substituted by a lactam moiety is described. A tandem ring opening-ring closure methodology consisting of a regiospecific ether cleavage of the tetrahydrofuroanilide 14b, followed by lactamization to α-oxygenated anilides 15b or 16b, gave α-O-functionalized-δ-valerolactams 12b or 13b, respectively. This approach is also compatible with the presence of ester and carbonyl chloride functions on the triiodophenyl moiety. A general synthesis of lactams 34–39 was also achieved. Further chemical modifications led to water soluble unsubstituted-lactams ( 34d, 35d, 37d) and α-hydroxy-lactams [ 42(d,e), 13(d,e) and 43] that are of interest as X-ray contrast agents.
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