Chemistry of Indoles carrying a Basic Function. Part 5. Some Observations while Constructing an Ergoline Ring by Stobbe Reaction

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István Moldvai, Eszter Temesvári-Major, Mihály Balázs, Eszter Gács-Baitz, Orsolya Egyed and Csaba Szántay


Abstract

Tricyclic indole derivative 11 affords the imide 12 under Stobbe reaction conditions rather than the expected intermediate containing an ergoline ring.


References

  1. Part 4, see: I. Moldvai, E. Temesváari-Major, E. Gács-Baitz, O. Egyed and Cs. Szántay, Hetrocycles, in press Search PubMed.
  2. K. Teranishi, S. Hayashi, S. Nakatsuka and T. Goto, Tetrahedron Lett., 1994, 35, 8173 CrossRef CAS.
  3. (a) R. E. Bowman, D. D. Evans, J. Guyett, H. Nagy, J. Weale, D. J. Weyell and A. C. White, J. Chem. Soc., Perkin Trans. 1, 1972, 1926 RSC; (b) R. E. Bowman, D. D. Evans, J. Guyett, J. Weale and A. C. White, J. Chem. Soc., Perkin Trans. 1, 1973, 760 RSC.
  4. Compound 10 was prepared from diethyl formylsuccinate (C. G. Wermuth, J. Org. Chem., 1979, 44, 2406) by Jones oxidation and subsequent treatment of the obtained acid with thionyl chloride. Search PubMed.
  5. W. S. Johnson and G. H. Daub, Org. React., 1951, 6, 1.
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