Chemistry of Heterocyclic Compounds

, Volume 51, Issue 7, pp 613–620 | Cite as

Diazonamide synthetic studies. Reactivity of N-unsubstituted benzofuro[2,3-b]indolines

  • Ilga Mutule
  • Toms Kalnins
  • Edwin Vedejs
  • Edgars Suna
Article

Benzofuro[2,3-b]indolines undergo ring opening in the presence of base to generate 3H-indolines. The latter can rearrange into 3-arylindoles through an intramolecular transfer of the methoxycarbonyl moiety from quaternary carbon to oxygen of phenol. The intermediate 3H-indolines can be isolated upon DMAP-catalyzed O-acylation of the phenol moiety with Boc2O.

Keywords

diazonamide DMAP hemiaminal indole 3H-indoline 

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Ilga Mutule
    • 1
  • Toms Kalnins
    • 1
  • Edwin Vedejs
    • 1
    • 2
  • Edgars Suna
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia
  2. 2.Department of ChemistryUniversity of MichiganAnn ArborU. S. A.

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