CiteScore: 2.1     h-index: 21

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.

Graphical Abstract

Water extract of onion catalyzed Knoevenagel condensation reaction: an efficient green procedure for synthesis of α-cyanoacrylonitriles and α-cyanoacrylates

Keywords

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