Abstract
Sequential functionalisation of 2-aryl-4-chloro-3-iodoquinolines via palladium–catalysed cross-coupling with phenylboronic acid followed by displacement of the 4-chloro atom from the resulting 2,3-diaryl-4-chloroquinolines with methoxide ion yielded 2,3-diaryl-4-methoxyquinolines. The latter were also prepared via Suzuki–Miyaura cross-coupling of 2-aryl-3-iodo-4-methoxyquinolines with phenylboronic acid. Demethylation of the methoxy compounds (BBr3) gave the 2,3-diaryl-4(1H)-quinolinones.
References
1.
Wang
M.
,
Liu
Y.
, and
Huang
Z.
, Tetrahedron Lett. , 2001 , 42 , 2553 .
2.
Hadjeri
M.
,
Mariotte
A.
, and
Boumendjel
A.
, Chem. Pharm. Bull , 2001 , 49 , 1352 .
3.
Xia
Y.
,
Yang
Z.
,
Xia
P.
,
Hackl
T.
,
Hamel
E.
,
Mauger
A.
,
Wu
J.
, and
Lee
K.J.
, J. Med. Chem. , 2001 , 44 , 3932 .
4.
De
S.K.
, and
Gibbs
R.A.
, Tetrahedron Lett , 2005 , 46 , 1647 .
5.
Maguire
M.P.
,
Sheets
K.R.
,
McVety
K.
,
Spada
A.P.
, and
Zilberstein
A.
, J. Med. Chem. , 1994 , 37 , 2129 .
6.
Alguinaldo
A.M.
,
Dalangin-Mallari
V.M.
,
Macabeo
A.P.G.
,
Byrne
L.T.
,
Abe
F.
,
Yamauchi
T.
, and
Franzblau
S.G.
, Int. J. Antimicrobial Agents , 2007 , 29 , 738 .
7.
Mphahlele
M.J.
,
Nwamadi
S.M.
, and
Mabeta
P.
, J. Heterocyclic Chem. , 2006 , 43 , 255 .
8.
Ryabukhin
S.V.
,
Volochnyuk
D.M.
,
Plaskon
A.S.
,
Naumchik
V.S.
, and
Tolmachev
A.A.
, Synthesis , 2007 , 1214 .
9.
Hoekstra
W.J.
,
Patel
H.S.
,
Liang
X.
,
Blane
J-PE.
,
Heyer
D.O.
,
Willson
T.M.
,
Iannone
M.A.
,
Kadwell
S.H.
,
Miller
L.A.
,
Pearce
K.H.
,
Simmons
G.A.
, and
Shearin
J.
, J. Med. Chem. , 2005 , 48 , 2243 .
10.
Miyaura
N.
,
Yanagi
T.
, and
Suzuki
A.
, Synth. Commun. , 1981 , 11 , 513 .
11.
Miyaura
N.
, and
Suzuki
A.
, J. Organomet. Chem. , 1999 , 576 , 147 .
12.
Zhang
P.
,
Kwong
F.Y.
,
Tian
Y.
, and
Cha
K.S.
, J. Org. Chem. , 1998 , 63 , 6886 .
13.
Tsvetkov
A.V.
,
Latyshev
G.V.
,
Lukashev
N.V.
, and
Beletskaya
I.P.
, Tetrahedron Lett , 2002 , 43 , 7267 .
14.
Ali
N.M.
,
McKillop
A.
,
Mitchell
M.B.
,
Rebelo
R.A.
, and
Wallbank
P.J.
, Tetrahedron , 1992 , 48 , 8117 .
15.
Miyaura
N.
,
Yamada
K.
,
Suginome
H.
, and
Suzuki
A.
, J. Am. Chem. Soc. , 1985 , 107 , 972 .
16.
Miyaura
N.
, and
Suzuki
A.
, J. Org. Chem. , 1990 , 68 , 130 .
17.
Kato
H.
,
Wakao
K.
,
Yamada
A.
, and
Mutoh
Y.
, J. Chem. Soc. Perkin Trans. 1 , 1988 , 189 .
18.
Jenekhe
S.A.
,
Lu
L.
, and
Alam
M.M.
, Macromolecules , 2001 , 34 , 7315 .
19.
Dziewonski
K.
,
Moszew
J.
,
Jastrzebska
W.
,
Kochanski
R.
,
Maksymowicz
J.
,
Stachowicz
P.
,
Strasikowna
I.
, and
Trzesinski
P.
, Rocz. Chem. , 1934 , 14 , 1123 .