Categories: Synthesis of N-Heterocycles >
Synthesis of quinolines and related compounds
Name Reactions
Recent Literature
An eco-friendly method allows the synthesis of 2,4-disubstituted quinolines via
Meyer-Schuster rearrangement of 2-aminoaryl ketones and phenylacetylenes in the
presence of a catalytic amount of zinc trifluoromethanesulfonate in the ionic
liquid [hmim]PF6. The ionic liquid can be recycled.
R. Sarma, D. Prajapati, Synlett, 2008,
3001-3005.
An environmentally friendly and highly efficient procedure gives
2,4-disubstituted quinoline derivatives by a simple alkynylation-cyclization
reaction of 2-aminoaryl ketones with phenylacetylenes in the presence of
indium(III) trifluoromethanesulfonate In(OTf)3 under microwave
irradiation and solvent-free conditions. The catalyst can be reused.
K. C. Lekhok, D. Prajapati, R. C. Boruah, Synlett, 2008,
655-658.
A Pd-catalyzed Wacker-type oxidative cyclization under air allows the
construction of 2-methylquinolines in good yields under mild conditions.
Z. Zhang, J. Tang, Z. Wang, Org. Lett., 2008,
10, 173-175.
A direct reaction between 2-aminobenzylic alcohol derivatives and either ketones
or alcohols in the presence of a base and benzophenone as hydride scavenger
allows the synthesis of polysubstituted quinolines without any transition-metal
catalyst.
R. Martínez, D. J. Ramón, M. Yus, J. Org. Chem., 2008,
73, 9778-9780.
An efficient and convenient nickel-catalyzed cyclization of 2-iodoanilines
with alkynyl aryl ketones gives 2,4-disubstituted quinolines. Naturally
occurring quinoline derivatives have been prepared in good yields. The
mechanism is discussed.
R. P. Korivi, C.-H. Cheng, J. Org. Chem., 2006, 71, 7079-7082.
A direct convergent two-component synthesis of quinolines from α,β-unsaturated
ketones and o-aminophenylboronic acid derivatives is regiocomplementary
to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic
rather than strongly acidic conditions.
J. Horn, S. P. Marsden, A. Nelson, D. House, G. G. Weingarten, Org. Lett.,
2008,
10, 4117-4120.
Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed
by acid-catalyzed Meyer-Schuster rearrangement gave 2-substituted and
2,4-disubstituted quinolines, respectively in good yields.
M. J. Sandelier, P. DeShong, Org. Lett., 2007,
9, 3209-3212.
4-Aryl and 4-vinyl quinolines were prepared via a sequential procedure involving
regioselective rhodium-catalyzed hydroarylation/hydrovinylation of
β-(2-aminophenyl)-α,β-ynones with arylboronic acids or potassium aryl and vinyl
trifluoroborates, followed by nucleophilic attack of the amino group onto the
carbonyl.
G. Abbiati, A. Arcadi, F. Marinelli, E. Rossi, M. Verdecchia, Synlett, 2006,
3218-3224.
A single-step conversion of various N-vinyl and N-aryl amides
to the corresponding pyridine and quinoline derivatives involves amide activation with trifluoromethanesulfonic anhydride in the
presence of 2-chloropyridine followed by π-nucleophile addition to the activated
intermediate and annulation. Compatibility of this chemistry with various functional groups is
noteworthy.
M. Movassaghi, M. D. Hill, O. K. Ahmad, J. Am. Chem. Soc.,
2007,
129, 10096-10097.
The direct conversion of amides, including sensitive N-vinyl amides,
to the corresponding trimethylsilyl alkynyl imines followed by a
ruthenium-catalyzed protodesilylation and cycloisomerization gives various
substituted pyridines and quinolines.
M. Movassaghi, M. D. Hill, J. Am. Chem. Soc.,
2006, 128, 4592-4593.
Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion
using Ts2O-tBuNH2 followed by in situ deprotection
with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity,
and with good functional group compatibility.
J. Yin, B. Xiang, M. H. Huffman, C. E. Raab, I. W. Davies, J. Org. Chem., 2007,
72, 4554-4557.
