Abstract
A novel heterogeneous silica nanosphere-supported ferrocene-containing ionic liquid catalyst (SiO2@Imid-Cl@Fc) was designed and synthesised and was systematically characterised by Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) and X-ray diffraction (XRD) analysis. The catalytic activity of the SiO2@Imid-Cl@Fc catalyst was tested in a one-pot, three-component reaction of malononitrile and kojic acid with 15 aromatic aldehydes at room temperature under ultrasound irradiation. The products were pyrano[3,2-b]pyran derivatives, four of which are new. The catalyst exhibited good catalytic performance over short reaction times (15–20 min) and could be recycled at least five times without significant loss of activity.
Keywords
References
1.
Polshettiwar V.
and
Varma R.S.
, Green Chem. , 2010 , 12 , 743 .
2.
Pradhan S.
,
Swarnima K.
and
Mishra B.G.
, J. Chem. Sci. , 2016 , 128 , 1119 .
3.
Gawande M.B.
,
Monga Y.
,
Zboril R.
and
Sharma R.
, Coordin. Chem. Rev. , 2015 , 288 , 118 .
4.
Niknam K.
and
Abolpour P.
, J. Chem. Sci. , 2015 , 127 , 1315 .
5.
Sharma R.
and
Sharma S.
, Dalton Trans. , 2014 , 43 , 1292 .
6.
Mehnert C.P.
,
Cook R.A.
,
Dispenziere N.C.
and
Afeworki M.
, J. Am. Chem. Soc. , 2002 , 124 , 12932 .
7.
Selvam T.
,
Machoke A.
and
Schwieger W.
, Appl. Catal. A: Gen. , 2012 , 445 , 92 .
8.
Mehnert C.P.
, Chem. Eur. J. , 2005 , 11 , 50 .
9.
Xin B.
and
Hao J.
, Chem. Soc. Rev. , 2014 , 43 , 7171 .
10.
Rashinkar G.
and
Salunkhe R.
, J. Mol. Catal. A-Chem. , 2010 , 316 , 146 .
11.
Rashinkar G.
,
Kamble S.
,
Kumbhar A.
and
Salunkhe R.
, Catal. Commun. , 2011 , 12 , 1442 .
12.
da Rocha D.R.
,
de Souza A.C.
,
Resende J.A.
,
Santos W.C.
,
dos Santos E.A.
,
Pessoa C.
,
de Moraes M.O.
,
Costa-Lotufo L.V.
,
Montenegro R.C.
and
Ferreira V.F.
, Org. Biomol. Chem. , 2011 , 9 , 4315 .
13.
El-Agrody A.M.
,
Fouda A.M.
and
Khattab E.S.A.
, Med. Chem. Res. , 2013 , 22 , 6105 .
14.
Ferreira S.B.
,
de Carvalho da Silva F.
,
Bezerra F.A.
,
Lourenco M.
,
Kaiser C.R.
,
Pinto A.C.
and
Ferreira V.F.
, Arch. Pharm. , 2010 , 343 , 81 .
15.
He M.
,
Yang N.
,
Sun C.
,
Yao X.
and
Yang M.
, Med. Chem. Res. , 2011 , 20 , 200 .
16.
Shahrisa A.
,
Miri R.
,
Esmati S.
,
Saraei M.
,
Mehdipour A.R.
and
Sharifi M.
, Med. Chem. Res. , 2012 , 21 , 284 .
17.
Schiller R.
,
Tichotová L.
,
Pavlík J.
,
Buchta V.
,
Melichar B.
,
Votruba I.
,
Kuneš J.
,
Špulák M.
and
Pour M.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 7358 .
18.
Hussain H.
,
Aziz S.
,
Schulz B.
and
Krohn K.
, Nat. Prod. Commun. , 2011 , 6 , 841 .
19.
Osman S.
,
Albert B.J.
,
Wang Y.
,
Li M.
,
Czaicki N.L.
and
Koide K.
, Chem. Eur. J. , 2011 , 17 , 895 .
20.
Bisht S.S.
,
Jaiswal N.
,
Sharma A.
,
Fatima S.
,
Sharma R.
,
Rahuja N.
,
Srivastava A.
,
Bajpai V.
,
Kumar B.
and
Tripathi R.P.
, Carbohyd. Res. , 2011 , 346 , 1191 .
21.
Wang S.
,
Milne G.
,
Yan X.
,
Posey I.J.
,
Nicklaus M.C.
,
Graham L.
and
Rice W.G.
, J. Med. Chem. , 1996 , 39 , 2047 .
22.
Wang Y.
,
Mo S.-Y.
,
Wang S.-J.
,
Li S.
,
Yang Y.-C.
and
Shi J.-G.
, Org. Lett. , 2005 , 7 , 1675 .
23.
Baghbanian S.M.
,
Rezaei N.
and
Tashakkorian H.
, Green Chem. , 2013 , 15 , 3446 .
24.
Banitaba S.H.
,
Safari J.
and
Khalili S.D.
, Ultrason. Sonochem. , 2013 , 20 , 401 .
25.
Li Y.
,
Zhao B.
,
Du B.
,
Jiang Q.
,
Wang X.
and
Cao C.
, Tetrahedron Lett. , 2013 , 54 , 227 .
26.
Asghari S.
,
Baharfar R.
,
Alimi M.
,
Ahmadipour M.
and
Mohseni M.
, Monatsh. Chem. , 2014 , 145 , 1337 .
27.
Meng X.X.
,
Du B.X.
,
Zhao B.
,
Li Y.L.
and
Chen C.F.
, J. Chem. Res. , 2013 , 37 , 638 .
28.
Mansoor S.S.
,
Ariffin A.
and
Sudhan S.
, Res. Chem. Intermed. , 2015 , 41 , 6687 .
29.
Asghari S.
and
Mohammadnia M.
, Res. Chem. Intermed. , 2016 , 42 , 1899 .
30.
Kataev E.A.
,
Reddy M.R.
,
Reddy G.N.
,
Reddy V.H.
,
Reddy C.S.
and
Reddy B.V.S.
, New. J. Chem. , 2016 , 40 , 1693 .
31.
Suslick K.S.
, Ultrasound: Its Chemical, Physical, and Biological Effects (Ed.), VCH Publishers , Weinheim , 1988 .
32.
Sweet J.D.
and
Casadonte D.J. Jr
, Ultrason. Sonochem. , 2001 , 8 , 97 .
33.
Ziarati A.
,
Safaei-Ghomi J.
and
Rohani S.
, Ultrason. Sonochem. , 2013 , 20 , 1069 .
34.
Pagadala R.
,
Maddila S.
and
Jonnalagadda S.B.
, Ultrason. Sonochem. , 2014 , 21 , 472 .
35.
Leonelli C.
and
Mason T.J.
, Chem. Eng. Process , 2010 , 49 , 885 .
36.
Tabassum S.
,
Govindaraju S.
and
Pasha M.A.
, Ultrason. Sonochem. , 2015 , 24 , 1 .
37.
Teimuri-Mofrad R.
,
Shahrisa A.
,
Gholamhosseini-Nazari M.
and
Arsalani N.
, Res. Chem. Intermed. , 2016 , 42 , 3425 .
38.
Shahrisa A.
,
Teimuri-Mofrad R.
and
Gholamhosseini-Nazari M.
, Synlett , 2015 , 26 , 1031 .
39.
Shahrisa A.
,
Teimuri-Mofrad R.
and
Gholamhosseini-Nazari M.
, Mol. Divers. , 2015 , 19 , 87 .
40.
Teimuri-Mofrad R.
,
Gholamhosseini-Nazari M.
,
Esmati S.
and
Shahrisa A.
, J. Chem. Sci. 2017 , doi: 10.1007/s11164-017-3024-2.
41.
Teimuri-Mofrad R.
,
Gholamhosseini-Nazari M.
,
Esmati S.
and
Shahrisa A.
, J. Chem. Sci. 2017 , doi: 10.1007/s12039-017-1343-x.
42.
He Y.
and
Yu X.
, Mater. Lett. , 2007 , 61 , 2071 .