Abstract
[MeC(OH)2]+ClO4- as a super acidic ionic liquid is an extremely active catalyst for Biginelli-type reactions. The present method is especially effective for the inactive aliphatic aldehydes. The solvent-free conditions, high catalytic activity, wide substrates tolerance and convenient product isolation make the protocol more advantageous.
References
1.
Kappe C.O.
,
Shishkin O.V.
,
Uray G.
, and
Verdino P.
, Tetrahedron , 2000 , 56 , 1859 .
2.
Kappe C.O.
, J. Med. Chem. , 2000 , 35 , 1043 .
3.
Biginelli P.
, Gazz. Chim. Ital. , 1893 , 23 , 360 .
4.
Shaabani A.
, and
Bazgir A.
, Tetrahedron Lett. , 2004 , 45 , 2575 .
5.
Ahn B.J.
,
Gang M.S.
,
Chae K.
,
Oh Y.
,
Shin J.
, and
Chang W.
, J. Ind. Eng. Chem. , 2008 , 14 , 401 .
6.
Zhang X.L.
,
Li Y.P.
,
Liu C.J.
, and
Wang J.D.
, J. Mol. Catal. A: Chem. , 2006 , 253 , 207 .
7.
Li J.T.
,
Han J.F.
,
Yang J.H.
, and
Li T.S.
, Ultrason. Sonochem. , 2003 , 10 , 119 .
8.
Heravi M.M.
,
Behbahani F.K.
, and
Oskooie H.A.
, Chin. J. Chem. , 2008 , 26 , 2203 .
9.
Liu C.
,
Wang J.
, and
Li Y.
, J. Mol. Catal. A: Chem. , 2006 , 258 , 367 .
10.
Zhang H.
,
Zhou Z.
,
Xiao Z.
,
Xu F.
, and
Shen Q.
, Tetrahedron Lett. , 2009 , 50 , 1622 .
11.
Rafiee E.
, and
Shahbazi F.
, J. Mol. Catal. A: Chem. , 2006 , 250 , 57 .
12.
Shobha D.
,
Chari M.A.
, and
Ahn K.H.
, Chin. Chem. Lett. , 2009 , 20 , 1059 .
13.
Salehi P.
,
Dabiri M.
,
Zolfigol M.A.
, and
Fard M.A.B.
, Tetrahedron Lett. , 2003 , 44 , 2889 .
14.
Gohain M.
,
Prajapati D.
, and
Sandhu J.S.
, Synlett , 2004 , 235 .
15.
Ahmed B.
,
Khan R.A.
, and
Habibullah K.M.
, Tetrahedron Lett. , 2009 , 50 , 2889 .
16.
Fang D.
,
Zhang D.Z.
, and
Liu Z.L.
, Monatsh Chem. , 2010 , 141 , 419 .
17.
Tamaddon F.
, and
Bistgani J.M.
, Synlett , 2011 , 2947 .
18.
Hall N.F.
, and
Conant J.B.
, J. Am. Chem. Soc. , 1927 , 49 , 3047 .
19.
Conant J.B.
, and
Hall N.F.
, J. Am. Chem. Soc. , 1927 , 49 , 3062 .
20.
Fu N.Y.
,
Yuan Y.F.
,
Cao Z.
,
Wang S.W.
,
Wang J.T.
, and
Peppe C.
, Tetrahedron , 2002 , 58 , 4801 .
21.
Wang M.
,
Jiang H.
, and
Wang Z.
, J. Chem. Res. , 2005 , 691 .
22.
Eynde J.J.V.
,
Audiart N.
,
Canonne V.
,
Michel S.
,
Haverbeke Y.V.
, and
Kappe C.
, Heterocycles 1997 , 45 , 1967 .
23.
Yadav J.S.
,
Reddy B.V.S.
,
Sridhar P.
,
Reddy J.S.S.
,
Nagaiah K.
,
Lingaiah N.
, and
Saiprasad P.S.
, Eur. J. Org. Chem. , 2004 , 552 .
24.
da Silva D.L.
,
Reis F.S.
,
Muniz D.R.
,
Ruiz A.L.T.G.
,
de Carvalho J.E.
,
Sabino A.A.
,
Modolo L.V.
, and
de Fátima A.
, Bioorg. Med. Chem. , 2012 , 20 , 2645 .
25.
Li Y.X.
, and
Bao W.L.
, Chin. Chem. Lett. , 2003 , 14 , 993 .
26.
Ren Y.M.
, and
Cai C.
, Monatsh. Chem. , 2009 , 140 , 49 .
27.
Liang B.
,
Wang X.
,
Wang J.X.
, and
Du Z.
, Tetrahedron , 2007 , 63 , 1981 .
28.
Pandit S.
,
Shivaji R.
, and
Pandit V.
; Rasayan J. Chem. , 2009 , 2 , 907 .
29.
Phucho I.T.
,
Tumtin S.
,
Nongpiur A.
,
Nongrum R.
, and
Nongkhlaw R.L.
, J. Chem. Pharm. Res. , 2010 , 2 , 214 .
30.
Mistry S.R.
, and
Maheria K.C.
, J. Mol. Catal. A: Chem. , 2012 , 355 , 210 .
31.
Salama M.A.
, and
El-Essa S.A.
, Indian J. Chem. B , 42B , 173 .
32.
Shaabani A.
,
Seyyedhamzeh M.
,
Maleki A.
, and
Hajishaabanha F.
, Tetrahedron , 2010 , 66 , 4040 .