Document Type: Original Research Article

Authors

Department of Chemistry, The Gandhigram Rural Institute-Deemed to be University, Gandhigram, Dindigul district, Tamilnadu-624 302, India

Abstract

A useful method for Knoevenagel condensation has been developed from the reaction between active methylene compound 1 and aldehyde 2 using the water extract of onion as a green catalyst. This method is suitable for variety of aldehydes including, substituted aromatic, aliphatic, α, β-unsaturated, and heterocyclic with malononitrile or ethyl cyanoacetate, and affords the α-cyanoacrylonitriles and α-cyanoacrylatesin excellent yields (Up to 98%). The products are isolated without column chromatography. The use of water extract of onion has several advantages such as low price, easy handling, simple work up procedure and environmentally benign.

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Main Subjects

[1]. Knoevenagel E. Eur. J. Inorg. Chem., 1896, 29:172

[2]. Khezri S.H., Mohammad M.V., Eftekhari S.B., Hashemi M.M., Baniasadi M.H., Green Chem. Lett. Rev., 2007, 1:61

[3]. Kim S.Y., Kwon P.S., Kwon T.W. Synth. Commun., 1997, 27:533

[4]. Hayashi T. J. Org. Chem., 1966, 31:3253

[5]. Girisha K.S., Kalluraya B., Narayana V., Padmashree. Eur. J. Med. Chem., 2010, 45:4640

[6]. Prajapati D., Sandhu S.J. J. Chem. Soc. Perkin Trans 1, 1993, 1:739

[7]. Zhou L.W., Tan H.B., Qiu S.X., Chen G.Y., Liu H.X., Zheng C. Tetrahedron Lett., 2017, 58:1817

[8]. Ghoshal A., Sarkar A.R., kumaran R.S., Hegde S., Manickam G., Jayashankaran J. Tetrahedron Lett., 2012, 53:1748

[9]. Hu W., Guan Z., Deng X., He Y.H. Biochim., 2012, 94:656

[10]. Xue F., MacKerell A.D., Heinzl G., Hom K. Tetrahedron Lett., 2013, 54:1700

[11]. Ding Y., Ni X., Gu M., Li S., Huang H., Hu Y., Catalysis Commun., 2015, 64:101

[12]. Biradar J.S., Sasidhar B.S., Eur. J. Med. Chem., 2011, 46:6112

[13]. Kudirka R.A., Barfield R.M., McFarland J.M., Drake P.M., Carlson A., Banas S., Zmolek W., Garofalo A.W., Rabuka D. ACS Med. Chem. Lett., 2016, 7:994

[14]. Robichaud B.A., Liu K.G. Tetrahedron Lett., 2011, 52:6935

[15]. Modak A., Mondal J., Bhaumik A. Appl. Catal., A 2013, 459:41

[16]. Wu J., Jiang H. Synth. Commun., 2011, 41:1218

[17]. Yi B.W., Yin Q.Y., Cai C. Org. Prep. Proced. Int., 2007, 39:71

[18]. Rao S.P., Venkataratnam R.V. Tetrahedron Lett., 1991, 32:5821

[19]. Martinez F., Orcajo G., Briones D., Leo P., Calleja G. Microporous Mesoporous Mater., 2017, 246:43

[20]. Reddy B.M., Patil M.K., Rao K.N., Reddy G.K. J. Mol. Cat. A: Chem., 2006, 258:302

[21]. Ying A., Wang L., Qiu F., Hu H., Yang J. C. R. Chim., 2015, 18:223

[22]. Islam S.K.M., Roy A.S., Dey R.C., Paul S. J. Mol. Cat. A: Chem., 2014, 394:66

[23]. Chena X., Arrueboc M., Yeunga K.L. Catal. Today, 2013, 204:140

[24]. Xu J., Shen K., Xue B., Li X.Y. J. Mol. Cat. A: Chem., 2013, 372:105

[25]. Kantam M.L., Choudary B.M., Reddy C.V., Rao K.K., Choudary B.M., Figueras F. Chem. Commun., 1998, 9:1033

[26]. Bennazha J., Zahouily M., Sebti S., Boukhari A., Holt E.M. Catal. Commun., 2001, 1:101

[27]. El Maadi A.,  Matthiesen L.C., Ershadi P., Baker J. Herron D.M., Holt M.E. J. Chem. Cryst., 2003, 33:757

[28]. Pullabhotla V.S.R.R., Rahman A., Jonnalagadda S.B., Catal. Commun., 2009, 10:365

[29]. Gupta R., Gupta M., Paul S., Gupta R. Bull. Korean. Chem. Soc., 2009, 30:2419

[30]. Ren Y., Lu J., Jiang O., Cheng X., Chen J. Chinese. J. Catal., 2015, 36:1949

[31]. Yang Y., Yao F.H., Xi F.G., Gao E.G. J. Mol. Cat A: Chem., 2014, 390:198

[32]. Göksu H., Gültekin E. Chem. Select, 2017, 2:458

[33]. Yu Y., Wu XJ., Zhao M., Ma Q., Chen J., Chen B., Sindoro M., Yang J., Han S, Lu Q., Zhang H. Angew. Chem. Int. Ed., 2016, 55:1

[34]. Sakthivel B., Dhakshinamoorthy A. J. Colloid Interface Sci., 2017, 485:75

[35] . Elhamifar D., Kazempoor S. J. Mol. Cat. A: Chem., 2016, 415:74

[36]. Zhao S., Wanga X., Zhang L., RSC Adv., 2013, 3:11691

[37]. Guo-hua G., Liang L., Ting Z., Jin-bao G., Ye L., Ming-yuan H, Chem. Res. Chin. Univ., 2007, 23:169 [38]. Harjani J.R., Nara S.J., Salunkhe M.M. Tetrahedron Lett., 2002, 43:1127

[39]. Balalaie S., Poursaeed A., Khoshkholgh M.J., Bijanzadeh H.R., Wolf E. C. R. Chim., 2012, 15:283 [40]. Sobrinho R.C.M.A., Oliveira P.M.D., D'Oca C.R.M., Russowsky D., D'Oca M.G.M. RSC Adv., 2017, 7:3214

[41]. Elhamifar D., Kazempoora S., Karimib B., Catal. Sci. Technol., 2016, 6:4318

[42]. Gawande M.B., Jayaram R.V., Catal. Commun., 2006, 7:931

[43]. Moison H., Texier-Boullet F., Foucaud A. Terrohedron, 1987, 43:537

[44]. Jain D., Khatri C., Rani A. Fuel Process. Technol., 2010, 91:1015

[45]. Hosseini-Sarvari M., Sharghi H., Etemad S. Chin. J. Chem., 2007, 25:1563

[46]. Texier-Boullet F., Foucaud A. Tetrahedron Lett., 1982, 23:4927

[47]. Moison H., Boullet T.F., Foucaud A. Tetrahedron Lett., 1987, 43:537

[48]. Malakooti R.., Mahmoudi H., Hosseinabadi R., Petrov S., Migliori A. RSC Adv., 2013, 3:22353

[49] . Choudary B.M., Kantam L.M., Sreekanth P., Bandopadhyay T., Figueras F, Tuel A. J. Mol. Catal. A: Chem., 1999, 142:361

[50]. Sarmaha B., Satpati B., Srivastava R. J. Colloid Interface Sci., 2017, 493:307

[51]. Dhakshinamoorthy A., Heidenreich N., Lenzen D., Stock N. CrystEngComm., 2017, 19:4187

[52] . Zhang A.Q., Zhang N., Hong S., Zhang M. Synth. Commun., 2009, 39:3024  

[53]. Dong F., Li Y.Q., Dai R.F. Chin. Chem. Lett., 2007, 18:266

[54] . Bezerra D.P., Azevedo D.C.S., Pinheiro L.G., Filho J.M., Oliveira A.C. Chem. Eng. J., 2015, 264:565 [55]. Al- Momani L.A., Lorbach V., Detry J., Geilenkirchen P., Muller M. ARKIVOC, 2016, VI:172

[56]. Li G.W., Xiao J., Zhang W.Q. Chin. Chem. Lett., 2014, 24:52   

[57] . Ammar H.B., Chtourou M., Frikha M.H. Trabelsi M. Ultrason.Sonochem., 2015, 22:559

[58]. Astle M.J., Gergel W.C. J. Org. Chem., 1956, 21:493

[59] . Balalaie S., Bararjanian M., Hekmat S., Salehi P. Synth. Commun., 2006, 36:2549

[60]. Suresh, Sandhu J.S. Green Chem. Lett. Rev., 2009, 2:189

[61]. Gangwar B.P., Palakollu V., Singh A., Kanvah S., Sharma S. RSC Adv., 2014, 4:55407

[62]. Sebti S., Smahi A., Solhy, A. Tetrahedron Lett., 2002, 43:1813

[63] . Skeist I., Handbook of Adhesives, 3rd ed.; Van Nostrand Reinhold: New York, 1990 ; p 463

[64]. Linden C.L., Shalaby S.W. J. Biomed. Mater. Res., 1997, 38:348

[65]. Forseth M., O’Grady K., Toriumi D. J. LongTerm Eff. Med. Implants, 1992, 2:221

[66]. Kimura K., Sugiura K. U.S. Pat. 4,321,180, 1982

[67] . Romero I.L., Malta J.B.N.S., Silva C.B., Mimica L.M.J., Soong K.H. Hida R.Y. Ind. J. Ophthalmol., 2009, 57:341

[68]. Kim Y.J., Moon J.H., Choi H.J., Ko B.M., Lee J.C., Min S.K., Yoo H.Y., Lee M.S. Dig. Endosc., 2011, 23: 326

[69]. Vauthier C., Dubernet C., Fattal E., Pinto-Alphandary H., Couvreur P. ‎Adv. Drug Deliv. Rev., 2003, 55:519

[70]. Tahtouh M., Kalman J.R., Reedy B.J. J. Polym. Sci. A: Polym. Chem., 2011, 49:257

[71] . Macgregor J.H., Pugh C. J. Chem. Soc., 1945, 0:535

[72] . Rammohan P. Open J. Org. Chem., 2013, 1:47

[73] . Deshmukh M.B., Patil S.S., Jadhav S.D., Pawar P.B. Synth. Commun., 2012, 42:1177

[74]. Patil S.S., Jadhav S.D., Deshmukh M.D. Indian. J. Chem., 2013, 52B:1172

[75] . Fonseca A.M., Monte F.J.Q., Oliveira M.C.F., Mattos M.C.M., Cordell G.A., Braz-Filho R., Lemos T.L.G. J. Mol. Catal. B: Enzyme., 2009, 57:78

[76] . Pal R. Int. J. Chem. Appl., 2013, 2:26

[77]. Saxena A., Tripathi R.M., Singh R.P., Dig J. Nanomater. Biostruct., 2010, 5:427

[78]. Abboud Y., Eddahbi A., Bouari A.E., Aitenneite H., Brouzi K., Mouslim J. J. Nanostructure Chem., 2013, 3:84

[79]. Corzo-Martinez, M., Corzo, N., Villamiel, M., Trends Food Sci.Technol., 2007, 18:609

[80] . Pawlikowska P.B., Gawron A., Pol. J. Pharmacol., 1995, 47:531

[81] . Augusti K.T. Indian J.Exp. Biol., 1996, 34:634

[82] . Cho J.W., Cho S.Y., Lee S.R., Lee K.S. Int. J. Mol. Med., 2010, 25:347

[83] . Gauglitz G.G., Korting H.C.,  Pavicic T., Ruzicka T., Jeschke M.G. Mol Med., 2011, 17:113

[84]. Chanprapaph K., Tanrattanakorn S., Wattanakrai P., Wongkitisophon P., Vachiramon V. Dermatol Res Pract., 2012, 2012:1

[85]. El-Demerdash F.M., Yousef M. I., Abou EI-Naga N.I., Food Chem. Toxicol., 2005, 43:57

[86] . Jaiswal N., Rizvi S.I. Current Nutr. Food Sci., 2012, 8:126

[87]. Ly T.N., Hazama C., Shimoyamada M., Ando H., Kato K., Yamauchi R., J. Agric. Food Chem., 2005, 53:8183

[88] . Thomson S.J., Rippon P., Butts C., Olsen S., Shaw M., Joyce N.I., Eady C.C. J. Agric. Food Chem., 2013, 61:10574

[89]. Imai S., Tsuge N., Tomotake M., Nagatome Y., Sawada H., Nagata T., Kumagai H. Nature, 2002, 419:625

[90]. Ascenzi P., Azzi A. IUBMB Life, 2003, 55:49

[91]. Block E. Sci. Am., 1985, 252:114

[92]. Prabakaran K., Sivakumar M., Perumal M.S. Chem. Select, 2017, 2:2363

[93] . Siebenhaar B., Casagrande B., Studer M., Blaser H.U. Can. J. Chem., 2001, 79:566

[94] . Saad G.R., Naoum M.M., Rizk H.A. Can. J. Chem., 1989, 67:284

[95] . Pasha M.A., Manjula K. J. Saudi. Chem. Soc., 2011, 15:283

[96]. Popp F.D., Catala A. J. Org. Chem., 1961, 26:2738

[97]. Yadav J.S., Subba Reddy B.V., Basak A.K.  Visali B., Narsaiah A.V., Nagaiah K. Eur. J. Org. Chem., 2004, 2004:546

[98]. Fuji K., Kawabata T., Node M., Fujita E. J. Org. Chem., 1984, 49:3214

 

How to cite this manuscript: Prabakaran Kaliyan,Sivakumar Matam, Seenivasa Perumal Muthu*. Water extract of onion catalyzed Knoevenagel condensation reaction: an efficient green procedure for synthesis of α-cyanoacrylonitriles and α-cyanoacrylates. Asian Journal of Green Chemistry, 3(2) 2019,137-153. DOI: 10.22034/ajgc.2018.137885.1079