Multicomponent synthesis of novel azo-linked 9-Aryl-1H-xanthene-1,8(2H)-diones using ionic liquid [BDBDMIm]HSO4

Document Type : Original Article

Authors

1 Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran

2 Department of Chemistry, Payame Noor University, Tehran, Iran

Abstract

The synthesis of ten novel azo dyes derived from 9-Aryl-1H-xanthene-1,8(2H)-dione derivatives from one equivalent of azo-linked salicylaldehydes and two equivalent of dimedone in the presence of 3,3'-(butane-1,4-diyl)bis(1,2-dimethyl-1H-imidazol-3-ium)hydrogensulfate, as a green media, in short reaction time and high yield is reported. Azo-linked aldehydes containing electron withdrawing groups (such as nitro and halide) or electron releasing groups (such as methyl and methoxy group) were employed and reacted well to give the corresponding xanthenes in the yields ranging from 82 to 95%. This method provides several advantages such as environmental friendliness, solvent free, simple work-up, and mild reaction condition. All of synthesized compounds were characterized by FT-IR, 1HNMR and 13CNMR spectroscopy and elemental analyses.

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References

[1]. T. Ueno, T. Honda, T. Jinboand, Chemical Abstracts, 106 (1987) 176.

[2]. H. Sato, M. Tsuzuki, H. Sato, Chemical Abstracts, 35 (1990) 112.
[3]. E. A. Schneider, Wrightman, F. Phytohormones and Related Compounds: A Comprehensive Treatise 1 (1978), 29-105.
[4]. T. Hideo, Jpn. Tokkyo Koho JP 56005480, 1981; Chemical Abstracts, 95 (1981) 80922b.
[5]. Lambert, R. W.  Martin, J. A.  Merrett, J. H.  Parkes, K. E. B. Thomas, G. J. PCT Int. Appl. WO 9706178. 1997; Chemical Abstracts, 126 (1997) 212377y.
[6]. W. H. Frishman, The New England Journal of Medicine, 308 (1983) 940.
[7]. A. Brossi, S. Teitel, G. V. Parry, Chapter 3 The Ipecac Alkaloids. The Alkaloids, 13 (1971) 189.
[8]. E. Schlittler, Chapter 13 Rauwolfia Alkaloids with Special Reference to the Chemistry of Reserpine. The Alkaloids, 8 (1965) 287.
[9]. E. A. Kolodina, M. Shvartsberg, N. P. Gritsan, Mendeleev Communications, 18 (2008) 302.
[10]. B. A. Hess Jr., L. J. Schaad, C.W. Holyoke Jr, Tetrahedron 28 (1972) 3657.
[11]. M. Balon, M. C. Carmona, M. A. Munoz, J. Hidalgo, Tetrahedron, 45 (1989) 7501.
[12]. K. Deres, C. H. Schroeder, A. Paessens, S. Goldmann, H. J. Hacker, O. Weber, T. Kramer, U. Niewoehner, U. Pleiss, J. Stoltefuss, E. Graef, D. Koletzki, R. N. A. Masantschek, A. Reimann, R. Jaeger, R. Grob, B. Beckermann, K. H. Schlemmer, D. Haebich, H. R. Waigmann, Science, 299 (2003) 893.                         
[13]. I. Couto, I. Tellitu, E. Domínguez, Arkivoc,(2011) 115.
[14]. D. R. Duguay, M. T. Zamora, J. M. Blacquiere, F. E. Appoh, C. M. Vogels, S. L. Wheaton, F. J.  Baerlocher, A. Decken, S. A. Westcott, Central European Journal of Chemistry, 6 (2008) 562.
[15]. B. B. Bhowmik, P. Ganguly, Spectrochimica Acta Part A, 61 (2011) 1997.
[16]. R. M. Ion, A. Planner, K. Wiktorowicz, D. Frackowiak, Acta Biochimica Polonica, 45 (1998) 833.
[17]. C. G. Knight, T. Stephens, Biochemical Journal, 258 (1989) 683.
[18]. G. Casiraghi, G. Casnati, M. Cornia, Tetrahedron Letters, 14 (1973) 679.
[19]. C. W. Kuo, J. M. Fang, Synthetic Communications,31 (2006) 877.
[20]. A. Jha, J. Beal, Tetrahedron Letters, 45 (2004) 8999.
[21]. B. Dos, K. Laxminarayana, M. Krishnaiah, Y. Srinivas, Synlett 12 (2007) 3107.
[22]. B. Rajitha, B. Sunil Kumar, Y. Thirupathi Reddy, P. N. Reddy, N. Sreenivasulu, Tetrahedron Letters, 46 (2005) 8691. 
[23]. M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes and Pigments, 76 (2008) 836.
[24]. G. H. Mahdavinia, Sh. Rostamizadeh, A. M. Amani, Z. Emdadi, Ultrasonics Sonochemistry, 16 (2009) 7.
[25]. G. Song, B. Wang, H. Luo, L. Yang, Catalysis Communications, 8 (2007) 673.
[26]. L. Nagarapu, S. Kantevari, V. C. Mahankhali, S. Apuri, Catalysis Communications, 8 (2007) 1173.
[27]. M. A. Pasha, V. P. Jayashankara, Bioorg. Med. Chem. Lett. 17 (2007) 621.
[28]. W. Su, D. Yang, C. Jin, B. Zhang, Tetrahedron Letters, 49 (2008) 3391. 
[29]. J. V. Madhav, Y. T. Reddy, P. N. Reddy, M. N. Reddy, S. Kuarm, P. A. Crooks, B. Rajitha, Journal of Molecular Catalysis A: Chemical, 304 (2009) 85.
[30]. M. Dabiri, M. Baghbanzadeh, M. Sh. Nikcheh, E. Arzroomchilar, Bioorganic & Medicinal Chemistry Letters, 18 (2008) 436.
[31]. M. A. Bigdeli, M. M. Heravi, G. H. Mahdavinia, Journal of Molecular Catalysis A: Chemical, 275 (2007) 25.
[32]. M. R. Yazdanbakhsh, H. Yousefi, M. Mamaghani, E. O. Moradi, M. Rassa, H. Pouramir, M. Bagheri, Journal of Molecular Liquids, 169 (2012) 21.  
[33]. A. Mohammadi, M. R. Yazdanbakhsh, N. Mahmoodi, Progress in Color, Colorants and Coatings, 5 (2012) 23.
[34]. E. O. Moradi-e-Rufchahi, M. R. Yazdanbakhsh, Journal of Color Science and Technology, 4 (2010) 83.
[35]. M. Nikpassand, L. Zare Fekri, P. Farokhian, Synthetic Communications, 45 (2015) 2303.
[36]. N. V. Plechkova, K. R. Seddon, Chemical Reviews, 37 (2008) 123.
[37]. P. A. Z. Suarez, J. Dupont, Journal de Chimie Physique, 95 (1998) 1626.
[38]. D. J. Adams, P. Dyson, S. T. Taverner, Chemistry in Alternative Reaction Media, John Wiley & Sons Ltd, (2004).
[39]. M. J. Earle, K. R. Seddon, Pure and Applied Chemistry, 72 (2000) 1391.
[40]. V. I. Parvulescu, C. Hardacre, Chemical Reviews, 107 (2007) 2615.
[41]. M. Nikpassand, M. Mamaghani, F. Shirini K. Tabatabaeian, Ultrasonics Sonochemistry, 17 (2010) 301.
[42]. L. Zare Fekri, M. Nikpassand, K. Hassanpour, Current Organic Chemistry, 12 (2015) 76.
Applied Chemistry Today
Volume 14, Issue 51
July 2019
Pages 325-336

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