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Novel spiro and fused heterocycles from the allylation of indigo

Journal Article


Abstract


  • The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindoloazepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the use of thermal versus microwave heating.

Authors


  •   Abdel-Hamid, Mohammed K. (external author)
  •   Bremner, John B.
  •   Coates, Jonathon A. (external author)
  •   Keller, Paul A.
  •   Milaender, Celia (external author)
  •   Torkamani, Yasmine (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)
  •   Willis, Anthony C. (external author)

Publication Date


  • 2009

Citation


  • Abdel-Hamid, M., Bremner, J. B., Coates, J. A., Keller, P. A., Milaender, C., Torkamani, Y. S., Skelton, B. W., White, A. H. & Willis, A. C. (2009). Novel spiro and fused heterocycles from the allylation of indigo. Tetrahedron Letters, 50 (50), 6947-6950.

Scopus Eid


  • 2-s2.0-70350519042

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4965

Number Of Pages


  • 3

Start Page


  • 6947

End Page


  • 6950

Volume


  • 50

Issue


  • 50

Place Of Publication


  • http://www.elsevier.com/wps/find/journaldescription.cws_home/233/description#description

Abstract


  • The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindoloazepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the use of thermal versus microwave heating.

Authors


  •   Abdel-Hamid, Mohammed K. (external author)
  •   Bremner, John B.
  •   Coates, Jonathon A. (external author)
  •   Keller, Paul A.
  •   Milaender, Celia (external author)
  •   Torkamani, Yasmine (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)
  •   Willis, Anthony C. (external author)

Publication Date


  • 2009

Citation


  • Abdel-Hamid, M., Bremner, J. B., Coates, J. A., Keller, P. A., Milaender, C., Torkamani, Y. S., Skelton, B. W., White, A. H. & Willis, A. C. (2009). Novel spiro and fused heterocycles from the allylation of indigo. Tetrahedron Letters, 50 (50), 6947-6950.

Scopus Eid


  • 2-s2.0-70350519042

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4965

Number Of Pages


  • 3

Start Page


  • 6947

End Page


  • 6950

Volume


  • 50

Issue


  • 50

Place Of Publication


  • http://www.elsevier.com/wps/find/journaldescription.cws_home/233/description#description