Abstract
The synthesis of a series of 2-arylpyrrolo[2,3,4-kl]acridin-1(2H)-ones, three of which are novel, though a one-pot three-component reaction of dimedone, various anilines, and isatin has been achieved in the presence of magnetite nanoparticles supported silica-sulfonic acid as catalyst under solvent-free conditions at 80 °C. The procedure avoids hazardous reagents/solvents and is more eco-friendly than existing methods. Fe3O4@silica-sulfonic acid is shown to be a highly efficient catalyst, and could be readily recovered using a simple external magnet and reused several times without any significant loss in activity. The catalyst was fully characterised by FTIR, SEM, XRD, EDX and VSM.
Get full access to this article
View all access options for this article.
References
1.
Ulaczyk-Lesanko
A.
, and
Hall
D. G.
, Curr. Opin. Chem. Biol. , 2005 , 9 , 266 .
2.
Domling
A.
, and
Ugi
I.
, Angew. Chem. Int. Ed. , 2000 , 39 , 3168 .
3.
Zhang
Y.
,
Zhao
Y.
, and
Xia
C.
, J. Mol. Catal. A: Chem. , 2009 , 306 , 107 .
4.
Suganuma
S.
,
Nakajima
K.
,
Kitano
M.
,
Yamaguchi
D.
,
Kato
H.
,
Hayashi
S.
, and
Hara
M.
, Solid State Sci. , 2010 , 12 , 1029 .
5.
Zamani
F.
, and
Hosseini
S. M.
, Catal. Commun. , 2014 , 43 , 164 .
6.
Gill
C. G.
,
Price
B. A.
, and
Jones
W. J.
, J. Catal. , 2007 , 251 , 145 .
7.
Iaoying
X.
,
Chen
L.
,
Han
B.
,
Yang
X.
, and
Duan
H.
, Polymer , 2010 , 51 , 2533 .
8.
Lu
A. H.
,
Salabas
E. L.
, and
Schüth
F.
, Angew. Chem. Int. Ed. , 2007 , 46 , 1222 .
9.
Naeimi
H.
,
Rashid
Z.
,
Zarnani
A. H.
, and
Ghahremanzadeh
R.
, New. J. Chem. , 2014 , 38 , 348 .
10.
Esmaeilpour
M.
,
Sardarian
A. R.
, and
Javidi
J.
, J. Appl. Catal. A-Gen. , 2012 , 445-446 , 359 .
11.
Maleki
A.
, Tetrahedron Lett. , 2013 , 54 , 2055 .
12.
Kiasat
A. R.
, and
Davarpanah
J.
, J. Mol. Catal. A-Chem. , 2013 , 373 , 46 .
13.
Li
B-L.
,
Zhang
M.
,
Hu
H-C.
,
Du
X.
, and
Zhang
Z-H.
, New. J. Chem. , 2014 , 38 , 2435 .
14.
Desbois
N.
,
Gardette
M.
,
Papon
J.
,
Labarre
P.
,
Maisonial
A.
,
Auzeloux
P.
,
Lartigue
C.
,
Bouchon
B.
,
Debiton
E.
, and
Blache
Y.
, Bioorg. Med. Chem. , 2008 , 16 , 7671 .
15.
Oppegard
L. M.
,
Ougolkov
A. V.
,
Luchini
D. N.
,
Schoon
R. A.
,
Goodell
J. R.
,
Kaur
H.
,
Billadeau
D. D.
,
Ferguson
D. M.
, and
Hiasa
H.
, Eur. J. Pharmacol. , 2009 , 602 , 223 .
16.
Goodell
J. R.
,
Ougolkov
A. V.
,
Hiasa
H.
,
Kaur
H.
,
Remmel
R.
,
Billadeau
D. D.
, and
Ferguson
D. M.
, J. Med. Chem. , 2008 , 51 , 179 .
17.
Kapuriya
N.
,
Kapuriya
K.
,
Zhang
X.
,
Chou
T. C.
,
Kakadiya
R.
,
Wu
Y. T.
,
Tsai
T. H.
,
Chen
Y. T.
,
Lee
T. C.
, and
Shah
A.
, Bioorg. Med. Chem. , 2008 , 16 , 5413 .
18.
Belmont
P.
, and
Dorange
I.
, Expert Opin. Ther., Pat. , 2008 , 18 , 1211 .
19.
Taraporewala
I. B.
, Tetrahedron Lett. , 1991 , 32 , 39 .
20.
Kavitha
H. P.
, Asian J. Chem. , 2004 , 16 , 1191 .
21.
Giorgio
C. D.
,
Shimi
K.
,
Boyer
G.
,
Delmas
F.
, and
Galy
J. P.
, Eur. J. Med. Chem. , 2007 , 42 , 1277 .
22.
Patel
N. A.
,
Surti
S. C.
,
Patel
R. G.
, and
Patel
M. P.
, Phosphorus Sulfur Silicon Relat., Elem. , 2008 , 183 , 2191 .
23.
Chauhan
P. M. S.
, and
Srivastava
S. K.
, Curr. Med. Chem. , 2001 , 8 , 1535 .
24.
Lee
Y.
,
Hyun
S.
,
Kim
H. J.
, and
Yu
J.
, Angew. Chem. Int. Ed. , 2007 , 47 , 134 .
25.
Wang
H.
,
Li
L.
,
Lin
W.
,
Xu
P.
,
Huang
Z.
, and
Shi
D.
, Org. Lett. , 2012 , 14 , 4598 .
26.
Jiang
B.
,
Wang
X.
,
Li
M. Y.
,
Wu
Q.
,
Ye
Q.
,
Xu
H. W.
, and
Tu
S. J.
, Org. Biomol. Chem. , 2012 , 10 , 8533 .
27.
Cao
C.
,
Xu
C.
,
Lin
W.
,
Li
X.
,
Hu
M.
,
Wang
J.
,
Huang
Z.
,
Shi
D.
, and
Wang
Y.
, Molecules , 2013 , 18 , 1613 .
28.
Kefayati
H.
,
Narchin
F.
, and
Rad-Moghadam
K.
, Tetrahedron Lett. , 2012 , 53 , 4573 .
29.
Karimi-Jaberi
A. Z.
, and
Jaafarizadeh
A.
, Res. Chem. Intermed. , 2014 , 40 , doi: 10.1007/s11164-014-1576-y .
30.
Ghasemzadeh
M. A.
,
Safaei-Ghomi
J.
, and
Molaei
H.
, C. R. Chimie , 2012 , 15 , 969 .
31.
Ghasemzadeh
M. A.
, and
Safaei-Ghomi
J.
, J. Chem. Res. , 2014 , 38 , 313 .
32.
Ghasemzadeh
M. A.
,
Safaei-Ghomi
J.
, and
Zahedi
S.
, J. Serb. Chem. Soc. , 2013 , 78 , 769 .
33.
Safaei-Ghomi
J.
, and
Ghasemzadeh
M. A.
, Chin. Chem. Lett. , 2012 , 23 , 1225 .
34.
Hedayati
V. R.
, and
Ghasemzadeh
M. A.
, J. Chem. Res. , 2015 , 39 , 56 .
35.
Hu
Y.
,
Zhang
Z.
;
Zhang
H.
,
Luo
L.
, and
Yao
S.
, J. Solid State Electrochem. , 2012 , 16 , 857 .
36.
Deng
Y. H.
,
Qi
D. W.
,
Deng
C. H.
,
Zhang
X. M.
, and
Zhao
D. Y.
, J. Am. Chem. Soc. , 2008 , 130 , 28 .