Abstract
A highly stereoselective synthesis of stilbenes (trans-1,2-diarylethylenes) was achieved under solvent-free conditions from aryl-aldehydes and aromatic substances bearing an activated methyl group in the presence of anhydrous K2CO3 and poly(ethylene glycol). This method avoided the need for completely anhydrous condition and use of a noxious organic solvent.
References
1.
Hahm S.G.
,
Lee S.W.
,
Lee T.J.
,
Cho S.A.
,
Chae B.
,
Jung Y.M.
,
Kim S.B.
, and
Ree M.
, J. Phys. Chem. B. , 2008 , 112 , 4900 .
2.
Kovalska V.B.
,
Kryvorotenko D.V.
,
Balanda A.O.
,
Losytskyy M. Yu.
,
Tokar V.P.
, and
Yarmoluk S.M.
, Dyes Pigments , 2005 , 67 , 47 .
3.
Qian Y.P.
,
Cai Y.J.
,
Fan G.J.
,
Wei Q.Y.
,
Yang J.
,
Zheng L.F.
,
Li X.Z.
,
Fang J.G.
, and
Zhou B.
, J. Med. Chem. , 2009 , 52 , 1963 .
4.
Zhang Y.S.
,
Li S.Z.
,
Li J.
,
Pan X.Q.
,
Cahoon R.E.
,
Jaworski J.G.
,
Wang X.
,
Jez J.M.
,
Chen F.
, and
Yu O.
, J. Am. Chem. Soc. , 2006 , 128 , 13030 .
5.
Minutolo F.
,
Sala G.
,
Bagnacani A.
,
Bertini S.
,
Carboni I.
,
Placanica G.
,
Prota G.
,
Rapposelli S.
,
Sacchi N.
,
Macchia M.
, and
Ghidoni R.
, J. Med. Chem. , 2005 , 48 , 6783 .
6.
Pan M.H.
,
Chang Y.H.
,
Badmaev V.
, and
Nagabhushanam K.
, J. Agric. Food Chem. , 2007 , 55 , 7777 .
7.
Soomro S.A.
,
Schulz A.
, and
Meier H.
, Tetrahedron , 2006 , 62 , 8089 .
8.
Pettit G.R.
,
Singh S.B.
, and
Cragg G.M.
, J. Org. Chem. , 1985 , 50 , 3404 .
9.
Pettit G.R.
,
Singh S.B.
,
Schmidt J.M.
,
Nivin M.L.
,
Hamel E.
, and
Lin C.M.
, J. Nat. Prod. , 1988 , 51 , 517 .
10.
Chang J.Y.
,
Yang M.F.
,
Chang C.Y.
,
Chen C.M.
,
Kuo C.C.
, and
Liou J.P.
, J. Med. Chem. , 2006 , 49 , 6412 .
11.
Cushman M.
,
Nagarathnam D.
,
Gopal D.
,
Chakraborti A.K.
,
Lin C.M.
, and
Hamel E.
, J. Med. Chem. , 1991 , 34 , 2579 .
12.
Lin C.M.
,
Singh S.B.
,
Chu P.S.
,
Dempcy R.O.
,
Schmidt J.M.
,
Pettit G.R.
, and
Hamel E.
, Mol. Pharmacol. , 1988 , 34 , 200 .
13.
Zhang X.Q.
,
Gu H.M.
,
Xu H.J.
,
Fu H.
,
Li B.L.
,
Guo J.
,
Lai Y.T.
, and
Wang W.
China Patent, 200610086180.5.
14.
Li B.L.
,
Guo J.
,
Zhang X.Q.
,
Lai Y.T.
, and
Hu H.M.
, Z. Naturforsch., B , 2007 , 62b , 244 .
15.
Li B.L.
,
Guo J.
,
Lai Y.T.
,
Wang W.
,
Zhang X.Q.
,
Gu H.M.
,
Xu H.J.
, and
Fu H.
, China Patent, 200610086179.2.
16.
Wang L.Y.
,
Zhang X.G.
,
Shi Y.P.
, and
Zhang Z.X.
, Dyes Pigments , 2004 , 62 , 21 .
17.
Zou S.
,
Zhang X.J.
,
Lin H.Z.
, China Patent, 200310111885.4.
18.
Li B.L.
,
Zhang Z.G.
,
Wang W.
,
Li J.
, and
Wang C.W.
, Z. Naturforsch., B , 2008 , 63b , 77 .
19.
Liu Y.
,
Liang J.
,
Liu X.H.
,
Fan J.C.
, and
Shang Z.C.
, Chin. Chem. Lett. , 2008 , 19 , 1043 .
20.
Timko J.M.
,
Moore S.S.
,
Walba D.M.
,
Hiberty P.C.
, and
Cram D.J.
, J. Am. Chem. Soc. , 1977 , 99 , 4207 .
21.
Wang M.L.
, and
Chang K.R.
, Ind. Eng. Chem. Res. , 1990 , 29 (1 ), 40 .
22.
Cao Y.Q.
,
Dai Z.
,
Zhang R.
, and
Chen B.H.
, Synth. Commun. , 2004 , 34 , 2965 .
23.
Silverstein R.M.
,
Baeeler G.C.
, and
Morrill T.C.
, Spectrometric identification of organic compounds , John Wiley and Sons , New York , 1981 , pp. 264 –265 .