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

Authors

Jasmine C. Jury, University of WollongongFollow
Nalivela Swamy, University of WollongongFollow
Arife Yazici, University of WollongongFollow
Anthony C. Willis, Australian National University
Stephen G. Pyne, University of WollongongFollow

RIS ID

31111

Publication Details

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. The Journal of Organic Chemistry, 74 (15), 5523-5527.

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.