Abstract
An efficient synthesis of a series of stilbenes is reported using 4-nitrotoluene and substituted arylaldehydes as starting materials in the presence of Cs2CO3 and polyethylene glycol under solvent-free microwave irradiation. Compared with conventional method, this strategy exhibited higher stereoselectivity, shorter reaction times and has a lower environmental impact.
References
1.
Saiko P.
,
Szakmary A.
,
Jaeger W.
, and
Szekere T.
, Mutat. Res. , 2008 , 658 , 68 .
2.
Baur J.A.
, and
Sinclair D.A.
, Nat. Rev. Drug Discov. , 2006 , 5 , 493 .
3.
Schultz T.P.
,
Cheng Q.
,
Boldin W.D.
,
Hubbard T.F.
,
Jin L.
,
Fisher T.H.
, and
Nicholas D.D.
, Phytochemistry , 1991 , 30 , 2939 .
4.
Schultz T.P.
,
Hubbard T.F.
,
Jin L.
,
Fisher T.H.
, and
Nicholas D.D.
, Phytochemistry , 1990 , 29 , 1501 .
5.
Pettit B.R.
, and
Anderson C.R.
, WO 2006124511 , 2006.
6.
Li Y.-Q.
,
Li Z.-L.
,
Zhao W.-J.
,
Wen R.-X.
,
Meng Q.-W.
, and
Zeng Y.
, Eur. J. Med. Chem. , 2006 , 41 , 1084 .
7.
Hart J.H.
, Annu. Rev. Phytopathol. , 1991 , 19 , 437 .
8.
Burns J.
,
Yokota T.
,
Ashihara H.
,
Lean M.E.J.
, and
Crozier A.
, J. Agric. Food Chem. , 2002 , 50 , 3337 .
9.
Bao J.
, and
Weber P.M.
, J. Am. Chem. Soc. , 2011 , 133 , 4164 .
10.
Pines D.
,
Pines E.
, and
Rettig W.
, J. Phys. Chem. A , 2003 , 107 , 236 .
11.
Soleas G.J.
,
Diamandis E.P.
, and
Goldberg D.M.
, Clin. Biochem. , 1997 , 30 , 91 .
12.
Geahlen R.L.
, and
McLaughlin J.L.
, Biochem. Biophys Res Commun. , 1989 , 165 , 241 .
13.
Bibby M.C.
, Drugs Future , 2002 , 27 , 475 .
14.
Hamel E.
, Med. Res. ReV. , 1996 , 16 , 207 .
15.
Roberts J.C.
, and
Pincock J. A.
, J. Org. Chem. , 2006 , 71 , 1480 .
16.
Burroughes J.H.
,
Bradley D.D.C.
,
Brown A.R.
,
Marks R.N.
,
Mackay K.
,
Friend R.H.
,
Burns P.L.
, and
Holmes A.B.
, Nature (Lond.) , 1990 , 347 , 539 .
17.
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 .
18.
Bosanac T.
,
Yang J.
, and
Wilcox C.S.
, Angew. Chem., Int. Ed , 2001 , 40 , 1875 .
19.
Kormos C.M.
, and
Leadbeater N.E.
, J. Org. Chem. , 2008 , 73 , 3854 .
20.
Morales-Morales D.
,
Redón R.
,
Yung C.
, and
Jensen C. M.
, Chem. Commun. , 2000 , 1619 .
21.
Kabir M.S.
,
Monte A.
, and
Cook J.M.
, Tetrahedron Lett. , 2007 , 48 , 7269 .
22.
Gedye R.
,
Smith F.
,
Westaway K.
,
Ali H.
,
Baldisera L.
,
Laberge L.
, and
Rousell J.
, Tetrahedron Lett. , 1986 , 27 , 279 .
23.
Salvadori J.
,
Balducci E.
,
Zaza S.
,
Petricci E.
, and
Taddei M.
, J. Org. Chem. , 2010 , 75 , 1841 .
24.
Lidström P.
,
Tierney J.
,
Wathey B.
, and
Westman J.
, Tetrahedron , 2001 , 57 , 9225 .
25.
Harjani J.R.
,
Nara S.J.
, and
Salunkhe M.M.
, Tetrahedron Lett. , 2002 , 43 , 1127 .
26.
Taha N.
,
Sasson Y.
, and
Chidambaram M.
, Appl. Catalysis A: General , 2008 , 350 , 217 .
27.
Wang M.-L.
, and
Chang K.-R.
, Ind. Eng. Chem. Res. , 1990 , 29 , 40 .
28.
Li X.B.
,
Wang L.
,
Zhang X.Q.
,
Gu H.M.
,
Guo J.
, and
Li B.L.
, J. Chem. Res. , 2010 , 34 , 489 .
29.
Wang L.-Y.
,
Zhang X.-G.
,
Shi Y.-P.
, and
Zhang Z.-X.
, Dyes Pigments , 2004 , 62 , 21 .
30.
Shengming Ma
,
Yu S.
,
Peng Z.
, and
Guo H.
, J. Org. Chem. , 2006 , 71 , 9865 .
31.
McConville M.
,
Saidi O.
,
Blacker J.
, and
Xiao J.
, J. Org. Chem. , 2009 , 74 , 2692 .
32.
Sun B.
,
Hoshino J.
,
Jermihov K.
,
Marler L.
,
Pezzuto J.M.
,
Mesecar A. D.
, and
Cushman M.
, Bioorg. Med. Chem. , 2010 , 18 , 5352 .
33.
Ketcham R.
,
Jambotkar D.
, and
Martinelli L.
, J. Org. Chem. , 1962 , 27 , 4666 .
34.
Wan P.
,
Davis M.J.
, and
Teo M.A.
, J. Org. Chem. , 1989 , 54 , 1354 .
35.
Tewari R.S.
,
Kumari N.
, and
Kendurkar P.S.
, J. Chem. Eng. Data , 1976 , 21 , 125 .