Abstract
A new preparation of 1,5-benzodiazepine derivatives has been achieved in good to excellent yields by the condensation of o-phenylenediamine with a variety of ketones employing nano-γ-Fe2O3–SO3H as catalyst under microwave irradiation and solvent-free conditions. Recyclable nano-γ-Fe2O3–SO3H provided high reactivity and was easily separated from the reaction mixture by using an external magnet. The advantages offered by this method are based on the principles of ‘green chemistry’: a facile and rapid reaction, no solvent, easy separation of products and good to excellent yields..
Keywords
References
1.
Whiting
P.J.
, Drug Discov. Today , 2003 , 8 , 445 .
2.
Wang
J.
,
Hug
D.
,
Gautschi
K.
, and
Wieser
H. G.
, J. Epilepsy , 1993 , 6 , 180 .
3.
Aversa
M.C.
,
Ferlazzo
A.
,
Giannetto
P.
, and
Kohnke
F. H.
, Synthesis , 1986 , 230 , 231 .
4.
Huang
W.K.
,
Cheng
C. W.
,
Chang
S. M.
,
Lee
Y. P.
, and
Diau
E. W. G.
, Chem. Commun. , 2010 , 46 , 8992 .
5.
Maiti
G.
,
Kayal
U.
,
Karmakar
R.
, and
Bhattacharya
R. N.
, Tetrahedron Lett. , 2012 , 53 , 1460 .
6.
Jadhav
A.V.
, and
Kim
H.
, RSC Adv. , 2013 , 3 , 5131 .
7.
Goswami
S.V.
,
Thorat
P. B.
, and
Bhusare
S. R.
, J. Chem. Sci. , 2013 , 125 , 745 .
8.
Varala
R.
,
Enugala
R.
, and
Adapa
S. R.
, J. Braz. Chem. Soc. , 2007 , 18 , 291 .
9.
Varala
R.
,
Enugala
R.
, and
Adapa
S. R.
, ARKIVOK , 2006 , xiii , 171 .
10.
Makone
S.S.
, and
Vyawahare
D. B.
, Der Chem. Sinica , 2012 , 3 , 1369 .
11.
Kuo
C.W.
,
Wang
C. C.
,
Kavala
V.
, and
Yao
C. F.
, Molecules , 2008 , 13 , 2313 .
12.
Pan
X.Q.
,
Zou
J. P.
,
Huang
Z. H.
, and
Zhang
W.
, Tetrahedron Lett. , 2008 , 49 , 5302 .
13.
Gao
S.T.
,
Liu
W. H.
,
Ma
J. J.
,
Wang
C.
,
Liang
Q.
, Synth. Commun. , 2009 , 39 , 3278 .
14.
Kappe
C.O.
, Angew. Chem. Int. Ed. , 2004 , 43 , 6250 .
15.
Wang
D.
, and
Astruc
D.
, Chem. Rev. , 2014 , 114 , 6949 .
16.
Gawande
M.B.
,
Monga
Y.
,
Zboril
R.
, and
Sharma
R. K.
, Coord. Chem. Rev. , 2015 , 288 , 118 .
17.
Koukabi
N.
,
Kolvari
E.
,
Khazaei
A.
,
Zolfigol
M. A.
,
Shirmardi-Shaghasemi
B.
, and
Khavasi
H. R.
, Chem. Commun. , 2011 , 47 , 9230 .
18.
Kidwai
M.
,
Jain
A.
, and
Bhardwaj
S.
, Mol. Divers. , 2012 , 16 , 121 .
19.
Gawande
M.B.
,
Luque
R.
, and
Zboril
R.
, ChemCatChem. , 2014 , 6 , 3312 .
20.
Madrakian
T.
,
Afkhami
A.
,
Zolfigol
M. A.
,
Ahmadi
M.
, and
Koukabi
N.
, Nano-micro Lett. , 2012 , 4 , 57 .
21.
Amoozadeh
A.
, and
Rahmani
S.
, J. Mol. Catal. A: Chem. , 2015 , 396 , 96 .
22.
Amoozadeh
A.
,
Golian
S.
,
Rahmani
S.
, RSC Adv. , 2015 , 5 , 45974 .
23.
Tabrizian
E.
,
Amoozadeh
A.
,
Rahmani
S.
,
Imanifar
E.
,
Azhari
S.
, and
Malmir
M.
, Chin. Chem. Lett. , 2015 , http://dx.doi.org/10.1016/j.cclet.2015.06.013
24.
Amoozadeh
A.
,
Rahmani
S.
, and
Kolvari
E.
, Catal. Commun. , 2014 , 56 , 184 .
25.
Koukabi
N.
,
Kolvari
E.
,
Zolfigol
M. A.
,
Khazaei
A.
,
Shaghasemi
B. S.
, and
Fasahati
B.
, Adv. Synth. Catal. , 2012 , 354 , 2001 .
26.
Amoozadeh
A.
,
Kolvari
E.
,
Koukabi
N.
, and
Otokesh
S.
, J. Chin. Chem. Soc. , 2015 , 62 , 501 .
27.
Otokesh
S.
,
Koukabi
N.
,
Kolvari
E.
,
Amoozadeh
A.
,
Malmir
M.
, and
Azhari
S.
, S. Afr. J. Chem. , 2015 , 68 , 15 .
