Abstract
The one-pot, four-component reaction of phthalic anhydride, hydrazine hydrate, aromatic aldehydes and malononitrile afford 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives in the presence of potassium carbonate in ethanol under reflux conditions. These conditions offer simplified operation, easy purification, excellent yields and environmentally benign reaction conditions. Also, this method avoids the use of expensive catalysts, toxic solvents and chromatographic separation.
Keywords
References
1.
Singh
M. S.
, and
Chowdhury
S.
, RSC Adv. , 2012 , 2 , 4547 .
2.
Dhakshinamoorthy
A.
, and
Garcia
H.
, Chem. Soc. Rev. , 2014 , 43 , 5750 .
3.
Majumder
A.
,
Gupta
R.
, and
Jain
A.
, Green Chem. Lett. Rev. , 2013 , 6 , 151 .
4.
LinNg
V.W.
,
Tan
J. P. K.
,
Leong
J.
,
Voo
Z. X.
,
Hedrick
J. L.
, and
Yang
Y. Y.
, Macromolecules , 2014 , 47 , 1285 .
5.
Jain
R. P.
, and
Vederas
J. C.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 3655 .
6.
Zhang
L.
,
Guan
L. P.
,
Sun
X. Y.
,
Wei
C. X.
,
Chai
K. Y.
, and
Quan
Z. S.
, Chem. Biol. Drug Des. , 2009 , 73 , 313 .
7.
Sinkkonen
J.
,
Ovcharenko
V.
,
Zelenin
K. N.
,
Bezhan
I. P.
,
Chakchir
B. A.
,
Al-Assar
F.
, and
Pihlaja
K.
, Eur. J. Org. Chem. , 2002 , 2046 .
8.
Raghuvanshi
D.S.
, and
Singh
K. N.
, Tetrahedron Lett. , 2011 , 52 , 5702 .
9.
Ghahremanzadeh
R.
,
Imani Shakibaei
G.
, and
Bazgir
A.
, Synlett , 2008 , 8 , 1129 .
10.
Nabid
M.R.
,
Rezaei
S. J. T.
,
Ghahremanzadeh
R.
, and
Bazgir
A.
, Ultrason. Sonochem. , 2010 , 17 , 159 .
11.
Reddy
M.V.
, and
Jeong
Y. T.
, Tetrahedron Lett. , 2013 , 54 , 3546 .
12.
Azarifar
A.
,
Nejat-Yami
R.
, and
Azarifar
D.
, J. Iran. Chem. Soc. , 2013 , 10 , 297 .
13.
Shah
N.M.
,
Patel
M. P.
, and
Patel
R. G.
, J. Heterocyclic Chem. , 2012 , 49 , 1310 .
14.
Song
S.H.
,
Zhong
J.
,
He
Y. H.
, and
Guan
Z.
, Tetrahedron Lett. , 2012 , 53 , 7075 .
15.
Shaterian
H.R.
,
Mohammadnia
M.
, J. Mol. Liq. , 2012 , 173 , 55 .
16.
Torkiana
L.
,
Dabiri
M.
,
Salehi
P.
, and
Bararjanian
M.
, Helv. Chim. Acta , 2011 , 94 , 1416 .
17.
Safaei-Ghomi
J.
,
Shahbazi-Alavi
H.
,
Ziarati
A.
,
Teymuri
R.
, and
Saberi
M. R.
, Chinese Chem. Lett. , 2014 , 25 , 401 .
18.
Shaterian
H.R.
, and
Mohammadnia
M.
, Res. Chem. Intermed. , 2014 , 40 , 371 .
19.
Mosaddegh
E.
, and
Hassankhani
A.
, Tetrahedron Lett. , 2011 , 52 , 488 .
20.
Pooladian
B.
,
Ghasemi
E.
, and
Karimi-Jaberi
Z.
, Green Chem. Lett. Rev. , 2014 , 7 , 60 .
21.
Karimi-Jaberi
Z.
, and
Pooladian
B.
, Synth. Commun. , 2013 , 43 , 1188 .
22.
Karimi-Jaberi
Z.
, and
Pooladian
B.
, Sci. World J. , 2012 , 208796 .
23.
Misra
M.
,
Sharma
R.
,
Kant
R.
,
Maulik
P. R.
, and
Tripathi
R. P.
, Tetrahedron Lett. , 2011 , 67 , 740 .
24.
Shen
L.
,
Cao
S.
,
Wu
J.
,
Li
H.
,
Zhang
J.
,
Wu
M.
, and
Qian
X.
, Tetrahedron Lett. , 2010 , 51 , 4866 .
25.
Kumar
T.D. A.
,
Swathia
N.
,
Navatha
J.
,
Subrahmanyam
C. V. S.
, and
Satyanarayana
K.
, J. Sulfur Chem. , 2015 , 36 , 105 .
