Abstract
An efficient and reusable catalyst, alkaline–modified Montmorillonite K10, has been developed and used in the Knoevenagel condensation. A series of condensation reactions based on ultrasound irradiation of different types of active methylene compounds and a variety of aromatic aldehydes showed the high efficiency of the prepared catalyst. This protocol has notable advantages, such as being eco-friendly, the ease of the work-up and reuse of the catalyst. The isolated compounds were synthesized in high yields (83–100%) in a short reaction time and were obtained, after crystallization, in pure form (IR, NMR and GC) without further purification. When ethyl cyanoacetate was used as active methylene compound, the reaction is highly stereoselective with only E geometry.
Similar content being viewed by others
References
Tietze LF (1996) Chem Rev 96:115–136
Parida KM, Rath D (2009) J Mol Catal A: Chem 310:93–100
Bartoli G, Bosco M, Carlone A, Dapozzo R, Galzerano P, Melichiorre P, Sambri L (2008) Tetrahedron Lett 49:2555–2557
Goa Y, Wu P, Tatsumi T (2004) J Catal 224:107–114
Cardillo G, Fabbroni S, Gentilucci L, Gianotti M, Tolomelli A (2003) Synth Commun 33:1587–1594
Narsaiah AV, Basak AR, Visali B, Nagaiah K (2004) Synth Commun 34:2893–2901
Calvino-Casilda V, Martin-Aranda RM, Lopez-Peinado AJ, Sobczak I, Ziolek M (2009) Catal Today 142:278–282
Rao PS, Venkataratnam RV (1991) Tetrahedron Lett 32:5821–5822
Ammar HB, Chtourou M, Frikha MH, Trabelsi M (2015) Ultrason Sonochem 22:559–564
Moison H, Texier-Boullet F, Faucaud A (1987) Tetrahedron 43:537–542
Saravanamurugan S, Palanichamy M, Hartmann M, Murugesan V (2006) Appl Catal A Gen 298:8–15
Corma A, Fornes V, Martin-Aranda RM, Reiy F (1992) J Catal 134:58–65
Reddy B, Patil MK, Rao KN, Reddy GK (2006) J Mol Catal A: Chem 258:302–307
Bennazha J, Zahouily M, Sebti S, Boukhari A, Holt EM (2001) Catal Commun 2:101–104
Gawande MB, Jayram RV (2006) Catal Commun 7:931–935
Sahani AJ, Burange AS, Jayaram RV (2018) Res Chem Intermed. https://doi.org/10.1007/s11164-018-3587-6
Yan H, Zhang HY, Wang L, Zhang Y, Zhao J (2018) Reac Kinet Mech Cat. https://doi.org/10.1007/s11144-018-1439-4
Subba Rao YV, Choudary BM (1991) Synth Commun 21:1163–1166
Moussaoui Y, Ben Salem R (2007) CR Chim 10:1162–1169
Yadav MK, Chudasama CD, Jasra RV (2004) J Mol Catal A: Chem 216:51–59
Hart MP, Brown DR (2004) J Mol Catal A: Chem 212:315–321
Chtourou M, Abdelhédi R, Frikha MH, Trabelsi M (2010) Ultrason Sonochem 17:246–249
Corma A, Martin-Aranda RM (1991) J Catal 130:130–137
Beavers WA, Culp RD (2004) U. S. Patent 6 794 325 B1
de la Fuente MA, Juarez M, de Rafael D, Olano A (1999) Food Chem 66:301–306
Ayoub M, Abdullah AZ (2013) Catal Commun 34:22–25
Martin-Aranda RM, Ortega-Cantero E, Rojas-Cervantes ML, Vicente-Rodriguez MA, Banares-Munoz MA (2002) Catal Lett 84:201–204
Molu ZB, Yurdakoc K (2010) Microporous Mesoporous Mater 127:50–60
Rode CV, Kshirsagar VS, Nadgeri JM, Patil KR (2007) Ind Eng Chem Res 46:8413–8419
Chtourou M, Frikha MH, Trabelsi M (2006) Appl Clay Sci 32:210–216
Duran-Valle CJ, Fonseca IM, Calvino-Casilda V, Picallo M, Lopez-Peinado AJ, Martin-Aranda RM (2005) Catal Today 107–108:500–506
Abdullaha AZ, Wibowoa TY, Zakaria R (2011) Chem Eng J 167:328–334
Postole G, Chowdhury B, Karmakar B, Pinki K, Banerji J, Auroux A (2010) J Catal 269:110–121
Climent MJ, Corma A, Iborna S, Velty A (2002) J Mol Catal A: Chem 182–183:327–342
Basavaiah D, Bakthadoss M (1998) Chem Commun 0:1639–1640
Zhao S, Wang X, Zhang L (2013) RSC Adv 3:11691–11696
Ye W, Jiang H, Yang XC (2011) J Chem Sci 123:331–334
Liu Y, Liang J, Liu XH, Fan JC, Shang ZC (2008) Chin Chem Lett 19:1043–1046
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Chtourou, M., Lahyani, A. & Trabelsi, M. Alkaline–modified montmorillonite K10: an efficient catalyst for green condensation reaction of aromatic aldehydes with active methylene compounds. Reac Kinet Mech Cat 126, 237–247 (2019). https://doi.org/10.1007/s11144-018-1495-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-018-1495-9