2,5-Diamide-substituted five-membered heterocycles. Challenging molecular synthons

C. Fabbro, S. Armani, L.-E. Carloni, F. De Leo, J. Wouters, D. Bonifazi,
Eur. J. Org. Chem. 2014, 2014, 5487-5500
DOI: 10.1002/ejoc.201402654


We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a “closed” conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.

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