Categories: Synthesis of N-Heterocycles >
Synthesis of quinolines and related compounds
Name Reactions
Recent Literature
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.
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.
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.
