CiteScore: 1.9     h-index: 21

Document Type : Original Research Article

Authors

1 Department of Chemistry, Shri Muktanand College, Gangapur, Tq.-Gangapur, Dist.-Aurangabad (MS) India 431-109

2 Department of Zoology, Shri Muktanand College, Gangapur, Tq.-Gangapur, Dist.-Aurangabad (MS) India 431-109

3 Department of Chemistry, Deogiri College, Station Road, Aurangabad (MS) India 431-005

Abstract

Ethyl methyl imidazolium hydroxide [EMIM][OH] ionic liquid catalyzed green protocol was developed for efficient and one-pot three-component condensation of various aromatic aldehydes, malononitrile, and dimedone under microwave irradiation for the synthesis of tetrahydrobenzo[b]pyran derivatives. The reaction proceeds in a short time period to afford moderate to excellent yield of products. The ionic liquid was recycled and reused for multiple time significantly, without a change in its catalytic efficiency. 

Graphical Abstract

Rapid and green synthesis of tetrahydrobenzo[b]pyran derivatives using reusable [EMIM][OH] ionic liquid

Keywords

[1]. Forsyth S.A., Pringle J.M., MacFarlane D.R. Aust. J. Chem., 2004, 57:113
[2]. Wasserscheid P., Keim W. Angewandte Chemie., 2000, 39:3772
[3]. Thorat V.V., Dake S.A., Deshmukh S.U., Rasokkiyam E., Uddin M.F., Pawar R.P. Lett. Org. Chem., 2013, 10:178
[4]. Ardhapure S.S., Siddiqui S.A, Tekale S.U., Ingle R.D., Shinde S.B., Pawar R.P. Eur. Chem. Bull., 2013, 2:320
[5]. Sarda S.R., Pathan M.Y., Paike V.V, Pachmase P.R., Jadhav W.N., Pawar R.P. Arkivoc, 2006, 2006:43
[6]. Farah M., Ake P. Drug Discov. Today, 2006, 11:3
[7]. Joshi V.M., Pawar R.P. Eur. Chem. Bull., 2013, 2:679
[8]. Larhed M., Hallberg A. Drug Discov. Today, 2001, 6:406
[9]. Gedye R., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., Rousell J. Tetrahedron Lett., 1986, 27:279
[10]. a) Martinez-Palou R. Mol. Div., 2006, 10:435; b) Nain S., Singh R., Ravichandran S. Adv. J. Chem. A, 2019, 2:94; c) Walter E.J., Ayi A.A., Chinyere A.A., Providence B.A., B. E. I.; Adv. J. Chem. A, 2019, 2:175.
[11]. Sarda S.R., Maslekar U.S., Jadhav W.N., Pawar R.P. E-Journal of Chemistry, 2009, 6:151
[12]. Flaxbart D. J. Am. Chem. Soc., 1997, 119:9086
[13]. Bonsignore L., Loy G., Secci D., Calignano A. Eur. J. Med. Chem., 1993, 28:517
[14]. Pore D.M., Unlade K.A., Dongare B.B., Desai U.V. Cat Lett., 2009, 132:104
[15]. Hatakeyama S., Ochi N., Numata H., Takano S. J. Chem. Soc. Commun., 1988, 1202
[16]. Martin N., Martínez‐Grau A., Seoane C., Marco J.L., Albert A., Cano F.H. Liebigs Ann. Chem., 1993, 7:801
[17]. Arnesto D., Horspool W.M., Martin N., Ramos A., Seaone C. J. Org. Chem., 1989, 54:3069 
[18]. El-Agrody A.M., Emam., El-Hakim M.H., Abdel-Lati M.S., Fakery A.H. J. Chem. Res., 1997, 320
[19]. Hekmatshoar R., Majedi S., Bakhtiari K. Catal. Commun., 2008, 9:307
[20]. Jin T.S., Wang A.Q., Wang X., Zhang J.S., Li T.S. Arkivoc, 2006, xiv:78
[21]. Devi I., Bhuyan P.J. Tetrahedron Lett., 2004, 45:8625
[22]. Balalaie S., Sheikh-Ahmadi M., Bararjanian M. Catal. Commun., 2007, 8:1724
[23]. Mobinikhaledi A., Ali M.Acta Chim. Slov., 2010, 57:931
[24]. Hazeri N., Maghsoodlou M.T., Fatemeh M., Kangani M., Saravani H., Molashahi E. Chin. J. Catal., 2014, 35:391
[25]. Wang X.S., Shi D.Q., Tu S.J., Yao C.S. Syn. Commun., 2003, 33:119
[26]. Lian X.Z., Huang Y., Li Y.Q.,  Zheng W.J. Monatshefte fur Chem., 2008, 139:129
[27]. a) Sheikhhosseini E., Ghazanfari D., Nezamabadi V. Iran. J. Cat., 2013, 3:197; b) Karami M., Gholami B., Hekmat-Zadeh T., Zare A. Chem. Method., 2019, 3:392; c) Momeni A.R., Samimi H.A., Vaezzadeh H. Chem. Method., 2018, 2:181,260; d) Kamran S., Amiri Shiri N. Chem. Method., 2018, 2:23
[28]. Balalaie S., Barajanin M., Amani A.M., Movassagh B. Synlett, 2006, 263
[29]. Fotouhi L., Heravi M.M., Fatehi A., Bakhtiari K. Tetrahedron Lett., 2007, 48:5379
[30]. Tu S., Gao Y., Guo C., Shi D., Lu Z. Syn. Commun., 2002, 32:2137
[31]. Mohammadi Ziarani G., Badiei A., Azizi M., Zarabadi P. Iran. J. Chem. Chem. Eng., 2011, 30:59
[32]. Yi Y., Hongyun G., Xiaojun L. J. Het. Chem., 2011, 48:1264