Categories: Synthesis of O-Heterocycles >
Synthesis of 3(2H)-furanones
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Recent Literature
A novel approach to 3(2H)-furanones combines a transition-metal-catalyzed
activation of alkynes with a heterocyclization and subsequent 1,2-alkyl shift.
Starting 2-hydroxy-2-alkynylcarbonyl compounds can be prepared by simple
oxygenation of alkynyl carbonyl compounds using 2-iodoxybenzoic acid (IBX).
S. F. Kirsch, J. T. Binder, C. Liébert, H. Menz, Angew. Chem. Int. Ed., 2006, 45, 5878-5880.
Gold-catalyzed cyclizations of 2-oxo-3-butynoic esters or
disubstituted-1,2-diones with a variety of nucleophiles offer an efficient
and straightforward route to substituted 3(2H)-furanones under mild
reaction conditions.
Y. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett.,
2006, 8, 3445-3448.
A sequence consisting of an electrophilic cyclization in the presence of N-iodosuccinimide
(NIS) and an 1,2-migration allows the construction of 4-iodo-3-furanones from
2-alkynyl-2-silyloxy carbonyl compounds. In a more versatile variant, AuCl3
catalyzes the tandem reaction in the presence of NIS to provide highly
substituted heterocycles in good yields.
B. Crone, S. F. Kirsch, J. Org. Chem., 2007,
72, 5435-5438.
An N-Heterocyclic carbene efficiently catalyzed an intramolecular
nucleophilic substitution reaction to yield benzopyrones and benzofuranones
depending on the substitution pattern.
J. He, J. Zheng, J. Liu, X. She, X. Pan, Org. Lett.,
2006, 8, 4637-4640.
