Synthesis of new 7-azabicyclo[2.2.1]heptane derivatives

José Marco-Contelles, Elena Gómez-Sánchez, Abdelouahid Samadi, Elena Soriano, Carolina Valderas, Mónica Álvarez-Pérez, Mría Do Carmo Carreiras

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


The synthesis of new 7-azabicyclo[2.2.1]heptane derivatives has been achieved in a four-step synthetic sequence, starting from readily available cyclohex-3-enecarboxylic acid, Curtius reaction, stereoselective bromination leading to major benzyl(cis-3, trans-4-dibromocyclohex-1-yl)carbamates (amides or sulfonamides), followed by NaH-mediated intramolecular cyclization. The synthesis and free radical cyclization of precursors 4-7, as well as the synthesis of a conformationally constrained epibatidine analogue 3 exploiting the reactivity of the 7-azabicyclo[2.2.1]hept-2-yl radical in intramolecular reactions, are described. The N-sulfonyl functional motif is the only one to afford a cyclized product when incorporated in the radical precursor.

Original languageEnglish
Pages (from-to)56-73
Number of pages18
JournalUnknown Journal
Issue number3
Publication statusPublished - 2010
Externally publishedYes


  • 7-azabicyclo[2.2.1]hept- 2-yl radical
  • 7-azabicyclo[2.2.1]heptane derivatives
  • Conformationally constrained epibatidine analogues
  • Intramolecular free radical reactions
  • N-(arylmethyl)cyclohex-3-enamines

ASJC Scopus subject areas

  • Organic Chemistry


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