Abstract
2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) was used as an efficient catalysts for a one-pot, three-component Mannich reaction of cyclohexanone or acetophenone with aromatic aldehydes and aromatic amines under solvent free condition. This protocol has the advantage of high yield, mild reaction conditions, lower catalyst loading and simple work up procedure.
References
1.
Kobayashi
S.
, and
Ishitani
H.
, Chem. Rev. , 1999 , 99 , 1069 .
2.
Arend
M.
,
Westermann
B.
, and
Risch
N.
, Angew. Chem. Int. Ed. , 1998 , 37 , 1045 .
3.
Arend
M.
, Angew. Chem. Int. Ed. , 1999 , 38 , 2873 .
4.
Cordova
A.
, Acc. Chem. Res. , 2004 , 37 , 102 .
5.
Duthaler
R.O.
, Angew. Chem. Int. Ed. , 2003 , 42 , 975 .
6.
Iimura
S.
,
Nobutou
D.
,
Manable
K.
, and
Kobayashi
S.
, Chem. Commun. , 2003 , 1644 .
7.
Pandey
G.
,
Singh
R. P.
,
Garg
A.
, and
Singh
V. K.
, Tetrahedron Lett. , 2005 , 46 , 2137 .
8.
Loh
R.T. P.
, and
Chen
S. L.
, Org. Lett. , 2002 , 4 , 3647 .
9.
Kikuchi
S.
,
Kobayashi
T.
, and
Hashimoto
Y.
, Tetrahedron Lett. , 2006 , 47 , 1973 .
10.
Takahashi
E.
,
Fujisawa
H.
, and
Mukaiyama
T.
, Chem. Lett. , 2004 , 33 , 936 .
11.
Komoto
I.
, and
Kobayashi
S.
, J. Org. Chem. , 2004 , 69 , 680 .
12.
Wang
R.
,
Li
B.
,
Huang
T.
,
Shi
L.
, and
Lu
X.
, Tetrahedron Lett. , 2007 , 48 , 2071 .
13.
List
B.
,
Pojarliev
P.
,
Biller
W. T.
, and
Martin
H. J.
, J. Am. Chem. Soc. , 2002 , 124 , 827 .
14.
Ibrahem
I.
,
Casas
J.
, and
Córdova
A.
, Angew. Chem. Int. Ed. , 2004 , 43 , 6528 .
15.
Mitsumori
S.
,
Zhang
H.
,
Cheong
P. H. Y.
,
Houk
K. N.
,
Tanaka
F.
, and
Barbas
C. F.
III
, J. Am. Chem. Soc. , 2006 , 128 , 1040 .
16.
Takahiko
A.
,
Jun
T.
, and
Hirotaka
K.
, Adv. Synth. Catal. , 2002 , 344 , 338 .
17.
Buckle
D.R.
, Encyclopaedia of reagent for organic synthesis ,
Paquette
L.A.
, ed.; John Wiley & Sons : Chichester, UK , 1995 ; Vol. 3 , pp. 1699 .
18.
Braude
E.A.
,
Linstead
R. P.
, and
Wooldridge
K. R.
, J. Chem. Soc. , 1956 , 3037 .
19.
Aubele
D.L.
, and
Floreancig
P. E.
, Org. Lett. 2002 , 4 , 3443 .
20.
Zhang
Y.H.
, and
Li
C. J.
, J. Am. Chem. Soc. , 2006 , 128 , 4242 .
21.
Tsang
A.S. K.
, and
Todd
M. H.
, Tetrahedron Lett. , 2009 , 50 , 1199 .
22.
Ollevier
T.
, and
Nadeau
E.
, J. Org. Chem. , 2004 , 69 , 9292 .
23.
Eftekhari-Sis
B.
,
Abdollahifar
A.
,
Hashemi
M. M.
, and
Zirak
M.
, Eur. J. Org. Chem. , 2006 , 5152 .
24.
Jafari
A.A.
,
Moradgholi
F.
, and
Tamaddon
F.
, Eur. J. Org. Chem. , 2009 , 1249 .
25.
Wu
H.
,
Sheen
Y.
,
Wan
L. Fancy
,
Zhang
P.
,
Chen
C.
, and
Wang
W.
, Tetrahedron , 2007 , 63 , 2404 .
26.
Manabe
K.
,
Mori
Y.
, and
Kobayashi
S.
, Tetrahedron , 2001 , 57 , 2537 .
27.
Guo
Q.
,
Liu
H.
,
Guo
C.
,
Luo
S.
,
Gu
Y.
, and
Gong
L.
, J. Am. Chem. Soc. , 2007 , 129 , 3790 .
28.
Akiyama
T.
,
Matsuda
K.
, and
Fuchibe
K.
, Synlett. , 2005 , 2 , 322 .
29.
Goswami
P.
, and
Das
B.
, Tetrahedron Lett. , 2009 , 50 , 2384 .
30.
Wang
R.
,
Li
B.
,
Huang
T. K.
,
Shi
L.
, and
Lu
X. X.
, Tetrahedron Lett. , 2007 , 48 , 2071 .