Abstract
Use of imidazolium ionic liquids [Bmim][CF3COO] and [Bmim]OH as a catalyst for synthesis of 3-arylidene(thio)chroman-4-ones by the condensation of (thio)chroman-4-ones and aromatic aldehydes under microwave irradiation conditions. A series of 3-arylidene(thio)chroman-4-ones were obtained as the only product and considerable increase of yield was founded within short time. The products 3-arylidene(thio)chromanones were assigned the (E)-configuration based on 1H NMR spectroscopic data.
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References
1.
Chen P.
, and
Yang J.S.
, Chem. Pharm. Bull. , 2007 , 55 , 655 .
2.
Purushothaman K.K.
,
Kalyani K.
,
Subramaniam K.
, and
Shanmughanathan S.P.
, Indian J. Chem., Sect. B , 1982 , 21 , 383 .
3.
McPherson D.D.
,
Cordell G.A.
,
Soejarto D.D.
,
Pezzuto J.M.
, and
Fong H.H.S.
, Phytochemistry , 1983 , 22 , 2835 .
4.
Wall M.E.
,
Wani M.C.
,
Manikumar G.
,
Taylor H.
, and
McGivney R.
, J. Nat. Prod. , 1989 , 52 , 774 .
5.
Nakib T.A.
,
Bezjak V.
,
Meegan M.J.
, and
Chandy R.
, Eur. J. Med. Chem. , 1990 , 25 , 455 .
6.
Desideri N.
,
Olivieri S.
,
Stein M.L.
,
Sgro R.
,
Orsi N.
, and
Conti C.
, Antiviral Chem. Chemother , 1997 , 8 , 545 .
7.
Basavaiah D.
,
Bakthadoss M.
, and
Pandiaraju S.
, Chem. Commun. , 1998 , 1639 .
8.
Sangwan N.K.
, and
Rastogi S.N.
, Indian J. Chem. Sect. B , 1981 , 20 , 135 .
9.
Wagner G.
,
Garbe C.
,
Vieweg H.
,
Brunn M.
, and
Dittrich A.
, Pharmazie , 1979 , 34 , 55 .
10.
Roberts J.F.
,
Alhassan M.
,
Xicluna A.
,
Ombetta J.E.
,
Mercier M.F.
,
Mercier R.
, and
Laude B.
, Bull. Soc. Chim. Fr. , 1993 , 130 , 788 .
11.
Farkas L.
,
Gottsegen A.
,
Nogradi M.
, and
Strelisky J.
, Punctata Tetrahedron , 1971 , 27 , 5049 .
12.
Pfeiffer P.
, and
von Bank G.
, J. Prakt. Chem. , 1938 , 151 , 319 .
13.
Woods L.
, and
Dix P.
, J. Org. Chem. , 1959 , 24 , 1126 .
14.
Levai A.
,
Dinya Z.
,
Schag J.B.
,
Toth G.
, and
Szollosy A.
Pharmazie , 1981 , 36 , 465 .
15.
Levai A.
, and
Szabo Z.
, Pharmazie , 1992 , 47 , 56 .
16.
Yang X.F.
,
Wang M.W.
, and
Li C.J.
, Org. Lett. , 2003 , 5 , 657 .
17.
Kim Y.J.
, and
Varma R.S.
, Tetrahedron Lett. , 2005 , 46 , 7447 .
18.
Ranu B.C.
, and
Jana R.
, J. Org. Chem. , 2005 , 70 , 8621 .
19.
Shen J.H.
,
Wang H.
,
Sun Y.
,
Liu H.C.
, and
Liu Z.M.
, Chin. J. Catal. , 2007 , 28 , 1009 .
20.
Li J.
,
Sun H.
,
Cai X.C.
, and
Dai L.Y.
, Chin. J. Org. Chem. , 2007 , 27 , 1296 .
21.
Liu B.Y.
,
Yang H.L.
,
Dong J.F.
,
Han J.
, and
Wei F.X.
, Acta. Sci. Natur. Univ. Sunyatseni. , 2007 , 46 , 278 .
22.
Siddaiah V.
,
Rao C.V.
,
Venkateswarlu S.
,
Krishnaraju A.V.
, and
Subbaraju G.V.
, Bioorg. Med. Chem. , 2006 , 14 , 2545 .
23.
Keane D.D.
,
Marathew G.
,
O'Sullivan W.I.
,
Philbin E.M.
,
Simons R.M.
, and
Teague P.C.
, J. Org. Chem. , 1970 , 6 , 2286 .
24.
Bennett P.
,
Donnelly J.A.
,
Meaney D.C.
, and
O'Boyle P.
, J. Chem. Soc. Perkin. Trans.1 , 1972 , 1554 .
25.
Runu B.C.
, and
Banerjee S.
, Org. Lett. , 2005 , 7 , 3049 .
26.
Pierre B.
,
Ana-Paula D.
,
Nicholas P.
,
Kuppuswamy K.
, and
Michael G.
, Inorg. Chem. , 1996 , 35 , 1168 .
27.
Li J.T.
,
Li H.Y.
,
Li H.Z.
, and
Xiao L.W.
, J. Chem. Res. , 2003 , 6 , 394 .