Facile Knoevenagel condensation Using Sulfonic Acid Functionalized Nanoporous silica (SBA-Pr-SO3H)

Document Type : Research Paper


1 Department of Chemistry, Alzahra University, P. O. Box 19938939973, Tehran, Iran

2 Department of Chemistry, Alzahra University, P.O.Box 19938939973, Tehran, Iran

3 School of Chemistry, College of Science, University of Tehran, Tehran, Iran


Knoevenagel condensation between barbituric acid and aldehyde was investigated in the presence of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) and resulted in the formation of arylidene and bis-arylidene barbiturates. Excellent yields and short reaction times are related to the high efficiency of SBA-Pr-SO3H that the reactions take place easily in its nano-pores. SBA-Pr-SO3H as an efficient heterogeneous nanoporous solid acid catalyst which was prepared by silica functionalization with (3-mercaptopropyl) trimethoxysilane followed by oxidation with H2O2, can be easily removed from the reaction mixture by simple filtration, and also recovered and reused without noticeable loss of reactivity.

[1]   Jursic B.S., J. Heterocycl. Chem., 38(2001), 655.
[2]   Ryabukhin S.V., Plaskon A.S., Volochnyuk D.M., Pipko S.E., Shivanyuk A.N., Tolmachev A.A., J. Comb. Chem., 9(2007), 1073.
[3]   Han J., Xu Y., Su Y., She X., Pan X., Catal. Commun., 9(2008), 2077.
[4]   Parvin M.N., Jin H., Ansari M.B., Oh S.M., Park S.E., Appl. Catal, A, 413–414(2012), 205.
[5]   Hu Y., He Y.H., Guan Z., Catal. Commun., 11(2010), 656.
[6]   Martins L., Hölderich W., Hammer P., Cardoso D., J. Catal., 271(2010), 220.
[7]   Gracia M.D., Jurado M.J., Luque R., Campelo J.M., Luna D., Marinas J.M., Romero A.A., Microporous Mesoporous Mater., 118(2009), 87.
[8]   Rajasekhar Pullabhotla V.S.R., Rahman A., Jonnalagadda S.B., Catal. Commun., 10(2009), 365.
[9]   Jursic B.S., Stevens E.D., Tetrahedron Lett., 44(2003), 2203.
[10]        Siddiqui Z.N., Khan T., Tetrahedron Lett., 54(2013), 3759.
[11]        Schulz D.W., MacDonald R.L., Brain Res., 209(1981), 177.
[12]        Gulliya K.S., Uses for barbituric acid analogs. U.S Patent, 5869494 (1999).
[13]        Gulliya K.S., Anti-cancer uses for barbituric acid analogs. U.S Patent, 5674870 (1997).
[14]        Sokmen B.B., Ugras S., Sarikaya H.Y., Ugras H.I., Yanardag R., Appl. Biochem. Biotechnol., 171(2013), 2030.
[15]        Mohammadi Ziarani G.,Shakiba Nahad M., Lashgari N., Badiei A., J. Nanostruct. Chem., 5(2014), 39.
[16]        Mohammadi Ziarani G., Faramarzi S., Lashgari N., Badiei A., J. Iran. Chem. Soc., 11(2014), 701.
[17]        Mohammadi Ziarani G., Asadi S., Badiei A., Mousavi S., Gholamzadeh P., Res. Chem. Intermed., 41(2015), 637.
[18]        Mohammadi Ziarani G., Mousavi S., Lashgari N., Badiei A., Shakiba Nahad M., Iran. J. Chem. Chem. Eng., 32(2013), 9.
[19]        Mohammadi Ziarani G., Lashgari N., Badiei A., J. Mol. Catal. A: Chem., 397(2015), 166.
[20]        Mohammadi Ziarani G., Mousavi S., Lashgari N., Badiei, A., J. Chem. Sci., 125(2013), 1359.
[21]        Shinde S., Rashinkar G., Kumbhar A., Kamble S., Salunkhe R., Helv. Chim. Acta, 94(2011), 1943.
[22]        Deb M.L., Bhuyan P.J., Tetrahedron Lett., 46(2005), 6453.
[23]        Lu J., Li Y., Bai Y., Tian M., Heterocycles, 63(2004), 583.
[24]        Borse B.N., Shukla S.R., Sonawane Y.A., Shankerling G.S., Synth. Commun., 43(2013), 865.