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Synthesis of 3(2H)-furanones
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A base-induced intramolecular cyclization of
(4-aryl-2,4-dioxobutyl)methylphenylsulfonium salts provides 2-unsubstituted
5-aryl-3(2H)-furanones in excellent yield within 10 min. This procedure
is simple, and can be carried out under mild conditions and an ambient
atmosphere.
S. Inagaki, K. Saito, S. Suto, S. Suto, H. Aihara, A. Sugawara, S. Tamura, T.
Kawano, J. Org. Chem., 2018, 83,
13834-13846.
A catalyst generated from the combination of (p-CF3C6H4)3PAuCl
and AgOTf cyclizes readily available γ-hydroxyalkynones under mild conditions to give substituted
3(2H)-furanones in good yields. This method is also applicable to the preparation of
2,3-dihydro-4H-pyran-4-ones.
M. Egi, K. Azechi, M. Saneto, K. Shimizu, S. Akai, J. Org. Chem., 2010,
75, 2123-2126.
A simple protocol for the efficient synthesis of 3(2H)-furanones by
cycloisomerization of allenic hydroxyketones is achieved in water and in the
absence of any expensive metal catalysts.
M. Poonoth, N. Krause, J. Org. Chem., 2011,
76, 1934-1936.
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.
The combination of Rh(II)/Pd(0) catalysts promotes a cyclization/allylic
alkylation cascade of stable α-diazo-δ-keto-esters to efficiently provide highly
substituted 3(2H)-furanones with a C2-quaternary center under mild
conditions. Remarkably, this binary catalytic system shows high chemo-, regio-,
and stereoselectivity and excellent functional group tolerance.
Q.-Q. Zhou, M. Cheng, Q.-Liu, B.-Q. Qu, X.-Y. Huang, F. Yang, K. Ji, Z.-S. Chen, Org. Lett., 2021, 23,
9151-9156.
A Rh(II)-catalyzed oxy-alkynylation of acceptor-acceptor carbenes using EBX
reagents provides diverse C2-quaternary alkyne-substituted benzofuran-3-ones and
2,2,4,5-tetrasubstituted 3(2H)-furanones under mild conditions with high
functional group compatibility. The key alkyne-transfer step is likely to occur
through a tandem process involving a β-addition, an α-elimination, and a
1,2-shift.
Q. Liu, Y.-T. Ma, X.-Y. Huang, Y.-Z. Li, F. Yang, S. Ali, K. Ji, Z.-S. Chen, Org. Lett., 2023, 25,
4044-4049.
An unexpected facile domino reaction of α,β-acetylenic γ-hydroxy nitriles with
arenecarboxylic acids affords 4-cyano-3(2H)-furanones in good yield. The
reaction is triggered by the addition of an arenecarboxylic acid to a triple
bond, followed by intramolecular transesterification-enol formation and Claisen
condensation of the ketoacetonitrile tautomer with ester functional group.
B. A. Trofimov, O. A. Shemyakina, A. G. Mal'kina, I. A. Ushakov, O. N. Kazheva,
G. G. Alexandrov, O. A. Dyachenko, Org. Lett., 2010,
12, 3200-3203.
A facile alkylative intramolecular cyclization of
3-alkoxycarbonyl-2-oxopropyldiphenylsulfonium salts provides 4-alkylated 3(2H)-furanones
in good yields under mild conditions.
S. Inagaki, M. Ukaku, A. Chiba, F. Takahashi, Y. Yoshimi, T. Morita, T. Kawano, J. Org. Chem.,
2016, 81, 8363-8369.
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.
The combination of Cu(OTf)2 and diphenyl phosphate (DPP-H)
catalyzes a facile tandem oxa-Nazarov cyclization and dibromination of
conjugated 1,2-diketones and N-bromosuccinimide to provide
2,4-dibromo-3(2H)-furanones in good yields.
H. Yin, Y. Tian, C. Guo, R. Song, D. Yang, J. Lv, J. Org. Chem., 2023, 88,
15862-15870.
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.