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.
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.
Jury
Jasmine C
JC
School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.
Swamy
Nalivela Kumara
NK
Yazici
Arife
A
Morgan
Ian R
IR
Willis
Anthony C
AC
Pyne
Stephen G
SG
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D019216:Metals, Heavy / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D019216:Metals, Heavy; D010880:Piperidines; D011725:Pyridines; D011758:Pyrroles; D011759:Pyrrolidines