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Metal-Catalyzed Cycloisomerization Reactions of cis-4-Hydroxy-5-alkynylpyrrolidinones and cis-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-b]pyrroles and Furo[3,2-b]pyridines

Journal Article


Abstract


  • Furo[3,2-b]pyrroles and furo[3,2-b]pyridines can be conveniently prepared in good yields from the cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones, respectively, using Ag(I), Pd(II)/Cu(I), or Au(I) catalysis. In one case, the cycloisomerization product was unstable and produced a furan derivative by a ring-opening reaction.

UOW Authors


  •   Jury, Jasmine C. (external author)
  •   Nalivela, Kumara Swamy (external author)
  •   Yazici, Arife (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2009

Citation


  • Jury, J. C., Nalivela, K., Yazici, A., Willis, A. C. & Pyne, S. G. (2009). Metal-Catalyzed Cycloisomerization Reactions of cis-4-Hydroxy-5-alkynylpyrrolidinones and cis-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-b]pyrroles and Furo[3,2-b]pyridines. Journal of Organic Chemistry, 74 (15), 5523-5527.

Scopus Eid


  • 2-s2.0-68049114671

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/3655

Has Global Citation Frequency


Number Of Pages


  • 4

Start Page


  • 5523

End Page


  • 5527

Volume


  • 74

Issue


  • 15

Abstract


  • Furo[3,2-b]pyrroles and furo[3,2-b]pyridines can be conveniently prepared in good yields from the cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones, respectively, using Ag(I), Pd(II)/Cu(I), or Au(I) catalysis. In one case, the cycloisomerization product was unstable and produced a furan derivative by a ring-opening reaction.

UOW Authors


  •   Jury, Jasmine C. (external author)
  •   Nalivela, Kumara Swamy (external author)
  •   Yazici, Arife (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2009

Citation


  • Jury, J. C., Nalivela, K., Yazici, A., Willis, A. C. & Pyne, S. G. (2009). Metal-Catalyzed Cycloisomerization Reactions of cis-4-Hydroxy-5-alkynylpyrrolidinones and cis-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-b]pyrroles and Furo[3,2-b]pyridines. Journal of Organic Chemistry, 74 (15), 5523-5527.

Scopus Eid


  • 2-s2.0-68049114671

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/3655

Has Global Citation Frequency


Number Of Pages


  • 4

Start Page


  • 5523

End Page


  • 5527

Volume


  • 74

Issue


  • 15