Abstract
A convenient method for the Michael addition of active methylene compounds to chalcone derivatives has been developed using the inexpensive and environmentally friendly reagent I2/K2CO3 at room temperature. The method is mild and proceeds with good to high yields.
References
1.
Clemens R.J.
, US Patent 5017649, 1991 .
2.
Nakamura N.
,
Shigemori K.
,
Otsuki T.
,
Mashimo Y.
,
Kawashima M.
,
Ikeda A.
,
Sato T.
, and
Saito H.
, WO Patent 0116203, 2001 .
3.
Richard M.G.
, US Patent 5993693, 1999 .
4.
Noomen A.
, Prog. Org. Coat. , 1997 , 32 , 137 .
5.
James H.E.
, and
Indubhai A.S.
, EP Patent 0022440, 1981 .
6.
Davey W.
, and
Gwilt J.R.
, J. Chem. Soc. , 1957 , 1015 .
7.
Garcia-Raso A.
,
Garcia-Raso J.
,
Campaner B.
,
Mestres R.
, and
Sinisterra J.V.
, Synthesis , 1982 , 1037 .
8.
Ganesh S.
, and
Sarkar A.
, Tetrahedron Lett. , 1991 , 32 , 1085 .
9.
Li T.L.
,
Cui Y.
,
Chen G.F.
,
Cheng Z.L.
, and
Li T.S.
, Synth. Commun. , 2003 , 33 , 353 .
10.
Yadav J.S.
,
Reddy B.V.S.
,
Reddy M.S.
, and
Prasad A.R.
, Tetrahedron Lett. , 2002 , 43 , 9703 .
11.
Bandgar B.P.
, and
Shaikh K.A.
, Tetrahedron Lett. , 2003 , 44 , 1959 .
12.
Saeeng R.
,
Sirion U.
,
Sahakitpichan P.
, and
Isobe M.
, Tetrahedron Lett. , 2003 , 44 , 6211 .
13.
Phukan P.
, J. Org. Chem. , 2004 , 69 , 4005 .
14.
Phukan P.
, Tetrahedron Lett. , 2004 , 45 , 4785 .
15.
Banik B.K.
,
Fernandez M.
, and
Alvarez C.
, Tetrahedron Lett. , 2005 , 46 , 2479 .
16.
Hessian K.O.
, and
Flynn B.L.
, Org. Lett. , 2006 , 8 , 243 .
17.
Bosco J.W.J.
,
Agrahari A.
, and
Saikia A.K.
, Tetrahedron Lett. , 2006 , 47 , 4065 .
18.
Rosnati V.
,
Saba A.
, and
Salimbeni A.
, Tetrahedron Lett. , 1981 , 22 , 167 .
19.
Toda F.
,
Takumi H.
,
Nagami M.
, and
Tanaka K.
, Hetrocycles , 1998 , 47 , 469 .
20.
Bram G.
,
Sansoulet J.
,
Galons H.
, and
Miocque M.
, Synth. Commun. , 1988 , 18 , 367 .
21.
Kim D.Y.
,
Huh S.C.
, and
Kim S.M.
, Tetrahedron Lett. , 2001 , 42 , 6299 .
22.
Dere R.T.
,
Pal R.R.
,
Patil P.S.
, and
Salunkhe M.M.
, Tetrahedron Lett. , 2003 , 44 , 5351 .
23.
Zhang Z.
,
Dong Y.W.
,
Wang G.W.
, and
Komatsu K.
, Synlett. , 2003 , 61 .
24.
Ooi T.
,
Ohara D.
,
Fukumoto K.
, and
Maruoka K.
, Org. Lett. , 2005 , 7 , 3195 .
25.
Ren Y.M.
, and
Cai C.
, Synth. Commun. , 2007 , 37 , 2209 .
26.
Ren Y.M.
, and
Cai C.
, Catal. Lett. , 2007 , 118 , 134 .
27.
Ren Y.M.
, and
Cai C.
, Catal. Commun. , 2008 , 9 , 1017 .
28.
Mohamed Z.
,
Bahija M.
,
Hind C.
,
Abdessamad M.
,
Bouchaib B.
, and
Mohamed O.
, Arkivoc , 2006 , xiii , 178 .
29.
Shi D.
,
Lu Z.
,
Wang S.
,
Tu S.
, and
Dai G.
, Synth Commun. , 1998 , 28 , 4003 .
30.
Gu C.L.
,
Liu L.
,
Sui Y.
,
Zhao J.L.
,
Wang D.
, and
Chen Y.J.
Tetrahedron: Asymmetry , 2007 , 18 , 455 .
31.
Li J.T.
,
Chen G.F.
,
Xu W.Z.
, and
Li T.S.
, Ultrason. Sonochem. , 2003 , 10 , 115 .