Abstract
A simple efficient method for the synthesis of novel amides of phenyl-1, 4-dioxyacetic acid as molecular tweezers under solvent-free conditions and microwave irradiation has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. The structures of the products were confirmed by IR, 1H NMR, MS spectra and elemental analyses and their binding properties were examined by UV-vis spectral titration. Preliminary results indicated that these molecular tweezers show good selectivity for neutral organic molecules.
References
1.
Albrecht
M.
,
Zauner
J.
,
Burgert
R.
,
Rottele
H.
, and
Frohlich
R.
, Mater. Sci. Eng., C , 2001 , 18 , 185 .
2.
Beer
P.D.
, and
Gale
P. A.
, Chem. Int. Ed. , 2001 , 40 , 486
3.
Mandado
M.
,
Ramón
J. M. H.
, and
Estévez
C. M.
, J. Mol. Struct. , 2008 , 1 , 854 .
4.
Kim
K.S.
, and
Kim
H. S.
, Tetrahedron , 2005 , 61 , 12366 .
5.
Bernier
N.
,
Carvalho
S.
,
Li
F.
,
Delgado
R.
, and
Felix
V.
, J. Org. Chem. , 2009 , 74 , 4819 .
6.
Lee
H.J.
,
Yoon
I. J.
,
Yoo
C. L.
,
Pyun
H. J.
,
Cha
G. S.
, and
Nam
H.
, Anal. Chem. , 2000 , 72 , 4694 .
7.
Hutchings
M.G.
,
Grossel
M. C.
,
Merckel
D. A. S.
,
Chippendale
A. M.
,
Kenworthy
M.
, and
McGeorge
G.
, Cryst. Growth Des. , 2001 , 1 , 339 .
8.
Mizuno
T.
,
Wei
W. H.
,
Eller
L. R.
, and
Sessler
J. L.
, J. Am. Chem. Soc. , 2002 , 124 , 1134 .
9.
Zhao
X.X.
,
Zhao
Z. G.
,
Li
X. L.
, and
Wu
X. M.
, Chin. Chem Lett. , 2009 , 20 , 397 .
10.
Kumar
V.
, and
Maitra
U.
, J. Org. Chem. , 2000 , 65 , 7764
11.
Anil
N.
,
Satish
A.
,
Umesh
, and
Bull
G.
, Chem. Soc. Jpn. , 1988 , 75 , 2161 .
12.
Wang
J.H.
, and
Zhang
Z.
, Chin. J. Appl. Chem. , 1994 , 11 , 4 .
13.
Martinez
L.E.
,
Leighton
J. L.
,
Carsten
D. H.
, and
Jacobsen
E. N.
, J. Am. Chem. Soc. , 1995 , 117 , 5897 .
14.
Leighton
J.L.
, and
Jacobsen
E. N.
, J. Org. Chem. , 1996 , 61 , 389 .
15.
Wei
T.B.
,
Liu
H.
,
Li
M. L.
, and
Zhang
Y. M.
J. Chem. Res. , 2005 , 7 , 432 .
16.
Yin
W.
,
Ma
Y.
, and
Xu
J. X.
, J. Org. Chem. , 2006 , 71 , 4312 .
17.
Rao
M.L. N.
,
Awasthi
D. K.
, and
Banerjee
D.
, Tetrahedron Lett. , 2007 , 48 , 431 .
18.
Qu
G.R.
,
Geng
M. W.
, and
Han
S. H.
, Chin. J. Org. Chem. , 2007 , 27 , 449 .
19.
Zhao
Z.G.
,
Liu
X. L.
, and
Zhou
C. E.
, Chin. Chem Lett. , 2007 , 18 , 1067 .
20.
Colacino
E.
,
Lamaty
F.
,
Martinez
J.
, and
Parrot
I.
Tetrahedron Lett. , 2007 , 48 , 5317 .
21.
Xue
C.H.
,
Hu
R.
,
Mu
Q. M.
,
Li
F.
, and
Chen
S. H.
, Acta Chim. Sinica. , 2000 , 58 , 717 .
22.
Moustafa
H.Y.
, J. Indian Chem. Soc. , 1996 , 73 , 435 .
