182758-12-9Relevant academic research and scientific papers
Heterocyclic nonionic X-ray contrast agents V: A facile conversion of 2-tetrahydrofuroamides into α-hydroxy-δ-valerolactams and a general synthesis of lactams conjugated to 2,4,6-triiodoisophthalamides
Marinelli,Arunachalam,Diamantidis,Emswiler,Fan,Neubeck,Pillai,Wagler,Chen,Natalie,Soundararajan,Ranganathan
, p. 11177 - 11214 (1996)
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-hydroxyl-lactams [42(d,e), 13(d,e) and 43d] that are of interest as X-ray contrast agents.
