Abstract
A series of 2-amino-4-aryl-5-oxo-4,5-dihydropyrano[3,2-c]chromene derivatives has been synthesised by the reaction of 4-hydroxycoumarin and substituted cinnamonitriles catalysed by KF-montmorillonite. The structures were characterised by IR and 1H NMR spectroscopic data and confirmed by X-ray diffraction analysis.
Keywords
References
1.
Soine
T.O.
, J. Pharm. Sci. , 1964 , 53 , 231 .
2.
Mitra
A.K.
,
De
A.
,
Karchaudhuri
N.
,
Misra
S.K.
, and
Mukhopadhyay
A.K.
, J. Ind. Chem. Soc. , 1998 , 75 , 666 .
3.
Romines
K.R.
,
Morris
J.K.
,
Howe
W.J.
,
Tomich
P.K.
,
Horng
M.M.
,
Chong
K.T.
,
Hinshaw
R.R.
,
Anderson
D.J.
,
Strohbach
J.W.
,
Tumer
S.R.
, and
Mizsak
S.A.
, J. Med. Chem. , 1996 , 39 , 4125 .
4.
Zhao
H.
,
Neamati
N.
,
Hong
H.
,
Mazumder
A.
,
Wang
S.
,
Sunder
S.
,
Milne
G.W.A.
,
Pommier
Y.
, and
Bruke
T.R.
, J. Med. Chem. , 1997 , 40 , 242 .
5.
Darbarwar
M.
, and
Sundaramurthy
V.
, Synthesis , 1982 , 337 .
6.
Boehm
H.J.
,
Boehringer
M.
,
Bur
D.
,
Gmeunder
H.
,
Huber
W.
,
Klaus
W.
,
Kostrewa
D.
,
Kuehne
H.
,
Luebbers
T.
,
Meunier-Keller
N.
, and
Mueller
F.
, J. Med. Chem. , 2000 , 43 , 2664 .
7.
Tao
J.
,
Hu
S.
,
Pacholec
M.
, and
Walsh
C.T.
, Org. Lett , 2003 , 5 , 3233 .
8.
Lafitte
D.
,
Lamour
V.
,
Tsvetkov
P.O.
,
Makarov
A.A.
,
Klich
M.
,
Deprez
P.
,
Moras
D.
,
Briand
C.
, and
Gilli
R.
, Biochem. , 2002 , 41 , 7217 .
9.
Yu
X.M.
,
Shen
G.
,
Neckers
L.
,
Blake
H.
,
Holzbeierlein
J.
,
Cronk
B.
, and
Blagg
B.S.J.
, J. Am. Chem. Soc. , 2005 , 127 , 12778 .
10.
Burlison
J.A.
, and
Blagg
B.S.J.
, Org. Lett , 2006 , 8 , 4855 .
11.
El-Agrody
A.M.
,
El-Latif
M.S.
,
Fakery
A.H.
, and
Bedair
A.H.
, J. Chem. Res. (S) , 2000 , 26 .
12.
Wang
J.
,
Shi
D.Q.
,
Zhuang
Q.Y.
,
Wang
X.S.
, and
Hu
H.W.
, J. Chem. Res. (S) , 2004 , 818 .
13.
Hauke
V.
,
Trendel
J.M.
, and
Albrecht
P.
, Tetrahedron Lett , 1994 , 35 , 2227 .
14.
Chalais
S.
,
Laszlo
P.
, and
Mathy
A.
, Tetrahedron Lett , 1986 , 27 , 2627 .
15.
Dauben
W.G.
,
Cogen
J.M.
, and
Behar
V.
, Tetrahedron Lett. , 1990 , 31 , 3241 .
16.
Cornelis
A.
, and
Laszlo
P.
, Synthesis , 1980 , 849 .
17.
Braibante
M.E.F.
,
Braibante
H.S.
,
Missio
L.
, and
Andricopulo
A.
, Synthesis , 1994 , 898 .
18.
Villemin
D.
, and
Martin
B.
, J. Chem. Res. (S) , 1994 , 146 .
19.
Cornelis
A.
,
Laszlo
P.
, and
Pennetreau
P.
, Bull. Soc. Chim. Belg. , 1984 , 93 , 961 .
20.
Cabral
J.
,
Laszlo
P.
, and
Mahe
L.
, Tetrahedron Lett. , 1989 , 30 , 3969 .
21.
Shi
D.Q.
,
Wang
X.S.
,
Yao
C.S.
, and
Mu
L.L.
, J. Chem. Res. (S) , 2002 , 344 .
22.
Zhuang
Q.Y.
,
Wu
N.
,
Shi
D.Q.
,
Tu
S.J.
, and
Wang
X.S.
, Chin. J. Org. Chem. , 2006 , 26 , 1217 .
23.
Wu
N.
,
Li
X.N.
,
Xu
X.
, and
Shi
D.Q.
, J. Chem. Res. , 2007 , 561 .
24.
Wu
N.
,
Li
X.N.
,
Wang
Y.M.
, and
Shi
D.Q.
, J. Chem. Res. , 2008 , 16 .
25.
Shi
D.Q.
,
Wu
N.
,
Zhuang
Q.Y.
, and
Zhang
Y.
, Acta Cryst. , 2004 , E60 , o2359 .
26.
Shi
D.Q.
,
Wu
N.
,
Zhuang
Q.Y.
, and
Zhang
Y.
, Acta Cryst. , 2004 , E60 , o87 .
27.
Shi
D.Q.
,
Wang
J.
,
Zhuang
Q.Y.
, and
Wang
X.S.
, Chin. J. Org. Chem. , 2006 , 26 , 643 .