Categories: Synthesis of O-Heterocycles > Furan Derivatives >
Synthesis of Furans
Name Reactions
Recent Literature
A 5-Endo-dig electrophilic cyclization of 1,4-diaryl but-3-yn-1-ones
with NBS or NIS/acetone and ICl/CH2Cl2 provides
3-halo-2,5-diarylfurans with high yields.
A. Sniady, K. A. Wheeler, R. Dembinski, Org. Lett., 2005, 7, 1769-1772.
Zinc chloride-catalyzed 5-endo-dig cycloisomerization of 1,4-di- and
1,2,4-trisubstituted but-3-yn-1-ones in dichloromethane at room temperature
provides 2,5-di- and 2,3,5-trisubstituted furans in high yields.
A. Sniady, A. Durham, M. S. Morreale, K. A. Wheeler, R. Dembinski, Org. Lett., 2007,
9, 1175-1178.
Different gold catalysts effect either selective bromine migration or
hydrogen shift in haloallenyl ketones, leading to the formation of 3- or
2-bromofurans, respectively. AuCl3-catalyzed transformations
include 1,2-halogen migrations via proposed halirenium intermediates and
allow for mild and efficient synthesis of various types of 3-halofurans.
A. W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc.,
2005, 127, 10500-10501.
Gold(III) porphyrin-catalyzed cycloisomerization of allenones gave the
corresponding furans in good to excellent yields (up to 98%) and with
quantitative substrate conversions. The Au(III) catalyst is recycable.
C.-Y. Zhou, P. W. H. Chang. C.-M. Che, Org. Lett.,
2006, 8, 325-328.
A mild, gold-catalyzed cascade reaction provides efficient access to highly
substituted furans. The substrates can be readily prepared from the
corresponding enones through cyclopropanation.
J. Zhang, H.-G. Schmalz, Angew. Chem. Int. Ed., 2006, 45, 6704-6707.
Easily accessible
propargyl vinyl ethers react in a cascade reaction of propargyl-Claisen
rearrangement and heterocyclization catalyzed by cationic triphenylphosphinegold(I)
to give tri- and tetrasubstituted furans.
M. H. Suhre, M. Reif, S. F. Kirsch, Org. Lett., 2005, 7, 3873-3876.
A new three-component cyclization catalyzed by palladium produces polysubstituted furans in good yields from readily
available substrates. A mechanism is proposed.
X.-H. Duan, X.-Y. Liu, L.-N. Guo, M.-C. Liao, W.-M. Liu, Y.-M. Liang, J. Org. Chem., 2005, 70, 6980-6983.
DABCO-catalyzed reactions of α-halo carbonyl compounds with
dimethyl acetylenedicarboxylate (DMAD) at room temperature gave polysubstituted furans and highly functionalized 2H-pyrans in
good yields.
M. Fan, Z. Yan, W. Liu, Y. Liang, J. Org. Chem., 2005, 70, 8204-8207.
The three-component coupling of aldehyde, dimethyl acetylenedicarboxylate (DMAD)
and cyclohexyl isocyanide proceeds efficiently in [bmim]BF4 ionic
medium under extremely mild conditions to afford 2-aminofurans in high yields.
The recovered ionic liquid was reused for five to six times with consistent
activity.
J. S. Yadav, B. V. S. Reddy, S. Shubashree, K. Sadashiv, J. J. Naidu, Synthesis,
2004, 2376-2380.
An efficient and highly versatile microwave-assisted Paal-Knorr condensation
of various 1,4-diketones gave furans, pyrroles and thiophenes in good yields.
In addition, transformations of the methoxycarbonyl moiety, such as Curtius
rearrangement, hydrolysis to carboxylic acid, or the conversion into amine
by reaction with a primary amine in the presence of Me3Al, are
described.
G. Minetto, L. F. Raveglia, A. Sega, M. Taddei, Eur. J. Org. Chem., 2005,
5277-5288.
Substituted 2-hydroxy-3-acetylfurans are synthesized by alkylation of
tert-butyl acetoacetate with an α-haloketone followed by treatment of the
obtained intermediate with trifluoroacetic acid (TFA). A second alkylation of
the intermediate followed by treatment with trifluoroacetic acid provides access
to disubstituted 2-methylfurans.
F. Stauffer, R. Neier, Org. Lett., 2000, 2,
3535-3537.
F. Stauffer, R. Neier, Org. Lett., 2000, 2,
3535-3537.
Coupling of acetylene, nitrile, and a titanium reagent generated new
azatitanacyclopentadienes in a highly regioselective manner. The subsequent
reaction with sulfonylacetylene and electrophiles gave substituted pyridines
virtually as a single isomer. Alternatively, the reaction of
azatitanacyclopentadienes with an aldehyde or another nitrile gave furans or
pyrroles having four different substituents again in a regioselective manner.
D. Suzuki, Y. Nobe, R. Tanaka, Y. Takayama, F. Sato, H. Urabe, J. Am. Chem. Soc.,
2005, 127, 7474-7479.
Various di- and triarylfurans were prepared in high yields from
but-2-ene-1,4-diones and but-2-yne-1,4-diones using formic acid in the
presence of a catalytic amount of palladium on carbon in poly(ethylene
glycol)-200 as solvent under microwave irradiation.
H. S. P. Rao, S. Jothilingam, J. Org. Chem., 2003, 68,
5392-5394.
H. S. P. Rao, S. Jothilingam, J. Org. Chem., 2003, 68,
5392-5394.
All isomers of (aminomethyl)furancarboxylic acids were prepared by the Delepine
reaction from alkyl (halomethyl)furancarboxylates. Treatment of the initially
formed quaternary salt with an ethanolic HCl solution gave the salts of the
corresponding unstable amino acid esters. Hydrolysis of the crude esters yielded
stable amino acid salts.
I. M. Lapina, L. M. Pevzner, A. A. Potekhin, Russ. J. Gen. Chem., 2006, 1304-1309.
