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

Chiara Fabbro, Simone Armani, Laure Elie Carloni, Federica De Leo, Johan Wouters, Davide Bonifazi

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)5487–5500
Number of pages14
JournalEuropean Journal of Organic Chemistry
Issue number25
Publication statusPublished - 2014


  • Amides
  • Conformation analysis
  • Furans
  • Heterocycles
  • Pyrroles
  • Rearrangement
  • Thiophenes


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