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 journalArticle

Abstract

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
Volume2014
Issue number25
DOIs
Publication statusPublished - 2014

Keywords

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

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  • Equipment

  • Datasets

    CCDC 950747: Experimental Crystal Structure Determination

    Armani, S. (Contributor), BONIFAZI, D. (Contributor), Carloni, L. (Contributor), De Leo, F. (Contributor), Fabbro, C. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2014

    Dataset

    CCDC 950749: Experimental Crystal Structure Determination

    Armani, S. (Contributor), BONIFAZI, D. (Contributor), Carloni, L. (Contributor), De Leo, F. (Contributor), Fabbro, C. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2014

    Dataset

    CCDC 950750: Experimental Crystal Structure Determination

    Armani, S. (Contributor), BONIFAZI, D. (Contributor), Carloni, L. (Contributor), De Leo, F. (Contributor), Fabbro, C. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2014

    Dataset

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