Abstract
An efficient catalyst-free procedure has been developed for one-pot aminomethylation of some electron-rich aromatic compounds such as 1- and 2-naphthols, indole, N-methylindol and benzamide, in [omim][BF4] ionic liquid at room temperature. The ionic liquid can be recovered and reused without any noticeable loss of performance.
Keywords
References
1.
Grumbach
H.J.
,
Arend
M.
, and
Risch
N.
, Synthesis , 1996 , 883 .
2.
Kleinman
E.F.
, In:
Trost
B.M.
, and
Fleming
I.
(eds), Comprehensive organic synthesis , 1991 , Vol. 2 , chap. 4.1, p. 893 . Pergamon Press , Oxford .
3.
Tramontini
M.
, and
Angiolini
L.
, Mannich bases, chemistry and uses , CRC Press , Boca Raton , 1994 .
4.
Traxler
P.
,
Trinks
U.
,
Buchdunger
E.
,
Mett
H.
,
Meyer
T.
,
Müller
M.
,
Regenass
U.
,
Rösel
J.
, and
Lydon
N.
, J. Med. Chem. , 1995 , 38 , 2441 .
5.
Arend
M.
,
Westermann
B.
, and
Risch
N.
, Angew. Chem. Int. Ed. , 1998 , 37 , 1044 .
6.
Wilkes
J.S.
, Green Chem. , 2002 , 4 , 73 .
7.
Welton
T.
, Chem. Rev. , 1999 , 99 , 2071 .
8.
Martins
M.A.P.
,
Frizzo
C.P.
,
Moreira
D.N.
,
Zanatta
N.
, and
Bonacorso
H.G.
, Chem. Rev. , 2008 , 108 , 2015 .
9.
Keskin
S.
,
Talay
D.K.
,
Akman
U.
, and
Hortacsu
O.
, J. Supercrit. Fluids , 2007 , 43 , 150 .
10.
Welton
T.
, Coord. Chem. Rev. , 2004 , 248 , 2459 .
11.
Hajipour
A.R.
, and
Rafiee
F.
, J. Iran. Chem. Soc. , 2009 , 6 , 647 .
12.
Sharifi
A.
,
Mirzaei
M.
, and
Naimi-Jamal
M.R.
, Monatsh. Chem. , 2001 , 132 , 875 .
13.
Mojtahedi
M.M.
,
Sharifi
A.
,
Mohsenzadeh
F.
, and
Saidi
M.R.
, Synth. Commun. , 2000 , 30 , 69 .
14.
Sharifi
A.
,
Mohsenzadeh
F.
, and
Naimi-Jamal
M.R.
, J. Chem. Res. (S), 2000 , 394 .
15.
Jha
A.
,
Paul
N.K.
,
Trikha
S.
, and
Cameron
T.S.
, Can. J. Chem. , 2006 , 84 , 843 –853 .
16.
Huang
P.J.J.
,
Cameron
T.S.
, and
Jha
A.
, Tetrahedron Lett. , 2009 , 50 , 51 .
17.
Chi
K.W.
,
Ahn
Y.S.
,
Shim
K.T.
,
Park
T.H.
, and
Ahn
J.S.
, Bull. Korean Chem. Soc. , 1999 , 20 , 973 .
18.
Feldman
J.R.
, and
Wagner
E.C.
, J. Org. Chem. , 1942 , 7 , 31 .
19.
Lieberman
S.V.
, and
Wagner
E.C.
, J. Org. Chem. , 1949 , 14 , 1001 .
20.
Fang
D.
,
Gong
K.
,
Zhang
D.Z.
, and
Liu
Z.L.
, Monatsh. Chem. , 2009 , 140 , 1325 .
21.
Fang
D.
,
Luo
J.
,
Zhou
L.X.
, and
Liu
Z.L.
, Catal. Lett. , 2007 , 116 , 76 .
22.
Caibo
Y.
, Synth. Commun. , 2010 , 40 , 3640 .
23.
Haslinger
E.
, and
Wolschann
P.
, Monatsh. Chem. , 1980 , 111 , 563 .
24.
Shriner
R.L.
,
Grillot
G.F.
, and
Teeters
W.O.
, J. Am. Chem. Soc. , 1946 , 68 , 946 .
25.
Assimomytis
N.
,
Sariyannis
Y.
,
Stavropoulos
G.
,
Tsoungas
P.G.
,
Varvounis
G.
, and
Cordopatis
P.
, Synlett , 2009 , 17 , 2777 .
26.
Li
J.T.
,
Sun
S.F.
, and
Sun
M.X.
, Ultrason. Sonochem. , 2011 , 18 , 42 .
27.
Park
S.
, and
Kazlauskas
R.J.
, J. Org. Chem. , 2001 , 66 , 8395 .
28.
Slattery
J.M.
,
Daguenet
C.
,
Dyson
P.J.
,
Schubert
T.J.S.
,
Krossing
I.
, Angew. Chem. Int. Ed. , 2007 , 46 , 5384 .
29.
Min
G.H.
,
Yim
T.
,
Yeong Lee
H.
,
Kim
H.J.
,
Mun
J.
,
Kim
S.
,
Oh
S.M.
, and
Kim
Y.G.
, Bull. Korean Chem. Soc. , 2007 , 28 , 1562 .
