Abstract
Nanostructured SiO2–H2SO)4 has been prepared and shown to efficiently catalyse the one-pot, three-component reaction of an aromatic aldehyde, malononitrile and a cyclic 1,3-diketone at reflux, to afford the corresponding 4H-chromene derivative in high yield. 4H-Chromene derivatives are important pharmacological agents exhibiting spasmolytic, diuretic, anticoagulant, anticancer, and antianaphylactic activities.
Keywords
References
1.
Ugi I.
, Angew. Chem. Int Ed Engl. , 1982 , 21 , 810 .
2.
Dömling A.
, and
Ugi I.
, Angew. Chem. Int Ed. , 2000 , 39 , 3169 .
3.
Dömling A.
, Chem. Rev. , 2006 , 106 , 17 .
4.
Foye W.O.
, Prinicipi di Chemico Farmaceutica; Piccin: Padova , Italy , 1991 , p. 416 .
5.
Andreani L.L.
, and
Lapi E.
, Bull. Chim. Farm. , 1960 , 99 , 583 .
6.
Zhang Y.L.
,
Chen B.Z.
,
Zheng K.Q.
,
Xu M.L.
,
Lei X.H.
, Yao Xue Xue Bao , 1982 , 17 , 17 . Chem. Abstr. , 1982, 96 , 135383e.
7.
Bonsignore L.
,
Loy G.
,
Secci D.
, and
Calignano A.
, Eur. J. Med. Chem. , 1993 , 28 , 517 .
8.
Skaker R.M.
, Pharmazie , 1996 , 51 , 148 .
9.
Abdolmohammadi S.
, and
Balalaie S.
, Tetrahedron Lett. , 2007 , 48 , 3299 .
10.
Heravi M.M.
,
Jani B.A.
,
Derikvand F.
,
Bamoharram F.F.
, and
Oskooie H.A.
, Catal. Commun. , 2008 , 10 , 272 .
11.
Khurana J.M.
,
Nand B.
, and
Saluja P.
, Tetrahedron , 2010 , 66 , 5637 .
12.
Kidwai M.
, and
Saxena S.
, Synth. Commun. , 2006 , 63 , 2737 .
13.
Abdel-Latif F.F.
,
Mashaly M.M.
, and
El-Gawish E.H.
, J. Chem. Res. , 1995 , 1220 .
14.
Shestopalov A.M.
,
EmelianovaYu M.
, and
Nesterov V.N.
, Russ. Chem. Bull. , 2003 , 52 , 1164 .
15.
Devi I.
, and
Bhuyan P.J.
, Tetrahedron Lett. , 2004 , 45 , 8625 .
16.
Fotouhi L.
,
Heravi M.M.
,
Fatehi A.
, and
Bakhtiari K.
, Tetrahedron Lett. , 2007 , 48 , 5379 .
17.
Jin T.-S.
,
Wang A.-Q.
,
Wang X.
,
Zhang J.-S.
, and
Li T.-S.
, Synlett , 2004 , 871 .
18.
Shi D.
,
Mou J.
,
Zhuang Q.
, and
Wang X.
, J. Chem. Res. , 2004 , 821 .
19.
Wang L.-M.
,
Shao J.-H.
,
Tian H.
,
Wang Y.-H.
, and
Liu B.
, J. Fluorine Chem. , 2006 , 127 , 97 .
20.
Wang X.-S.
,
Shi D.-Q.
,
Tu S.-J.
, and
Yao C.-S.
, Synth. Commun. , 2003 , 33 , 119 .
21.
Balalaie S.
,
Bararjanian M.
,
Mohammad A.
, and
Movassagh B.
, Synlett , 2006 , 263 .
22.
Balalaie S.
,
Bararjanian M.
, and
Sheikh-Ahmadi M.
, Synth. Commun. , 2007 , 37 , 1097 .
23.
Sadeghi B.
,
Mirjalili B.F.
, and
Hashemi M.M.
, Tetrahedron Lett. , 2008 , 49 , 2575 .
24.
Mirjalili B.F.
,
Hashemi M.M.
,
Sadeghi B.
, and
Emtiazi H.
, J. Chin. Chem., Soc. , 2009 , 56 , 386 .
25.
Gao S.
,
Hsuan Tsai C.
,
Tseng C.
, and
Yao C.F.
, Tetrahedron , 2008 , 64 , 9143 .