Abstract
Michael reactions of indoles with α,β-unsaturated ketones were carried out under microwave irradiation in water, affording the corresponding products in good to excellent yields. The calix[6]arene sulfonic acids bearing pendent aliphatic chains, as efficient surfactant-type acid catalysts, can be recovered after simple work-up and reused directly several times without loss of catalytic activity.
References
1.
Sundberg R.J.
, Indoles. Academic Press , San Diego , 1996 .
2.
Maiti G.
, and
Kundu P.
, Synth. Commun. , 2007 , 37 , 2309 .
3.
Kumar V.
,
Kaur S.
, and
Kumar S.
, Tetrahedron Lett. , 2006 , 47 , 7001 .
4.
Reddy A.V.
,
Ravinder K.
, and
Goud T.V.
, Tetrahedron Lett. , 2003 , 44 , 6257 .
5.
Ji S.J.
, and
Wang S.Y.
, Ultrason. Sonochem. , 2005 , 12 , 339 .
6.
Zhang H.B.
,
Liu L.
, and
Liu Y.L.
, Synth. Commun. , 2007 , 37 , 173 .
7.
Damodiran M.
,
Kumar R.S.
, and
Sivakumar P.M.
, J. Chem. Sci. , 2009 , 121 , 65 .
8.
Gu Y.L.
,
Ogawa C.
, and
Kobayashi S.
, Org. Lett. , 2007 , 9 , 175 .
9.
Ma J.M.
,
Ng S.
, and
Yong Y.J.
, Chem. Asian J. , 2010 , 5 , 778 .
10.
Shinkai S.
,
Mori H.
, and
koreishi T.
, J. Am. Chem. Soc. , 1986 , 108 , 2409 .
11.
Shinkai S.
,
Araki K.
, and
Manabe O.
, J. Am. Chem. Soc. , 1988 , 110 , 7214 .
12.
Shinkai S.
,
Arimura T.
, and
Araki K.
, J. Chem. Soc. Perkin Trans. , 1989 , 2039 .
13.
Liu Y.L.
,
Liu L.
, and
Wang Y.L.
, Green Chem. , 2008 , 10 , 635 .
14.
Baghbanian S.M.
,
Babajani Y.
,
Tashakorian H.
,
Khakscar S.
, and
Farhang M.
, Comptes Rendus Chimie , 2013 , 16 , 129 .
15.
Yu C.J.
, and
Liu C.J.
, Molecules , 2009 , 14 , 3225 .
16.
Li J.T.
,
Dai H.G.
, and
Xu W.Z.
, J. Chem. Res. , 2006 , 42 .
17.
Gu D.G.
,
Ji S.J.
, and
Wang H.X.
, Synth. Commun. , 2008 , 38 , 1212 .
18.
Wang W.T.
,
Liu X.H.
, and
Cao W.D.
, Chem. Eur. J. , 2010 , 16 , 1664 .
19.
Kanwar D.
,
Rani R.
, and
Agarwal J.
, Ind. J. Chem. , 2010 , 49B , 1290 .
20.
Trost B.M.
, and
Quancard J.
, J. Am. Chem. Soc. , 2006 , 128 , 6314 .
21.
Schiffner J.A.
,
Woste T.H.
, and
Oestreich M.
, Eur. J. Org. Chem. , 2010 , 180 .
