Choline Chloride-Oxalic Acid as a Deep Eutectic Solvent Promoted Synthesis of Aroylamido Coumarin Derivatives in Excellent Yields
محورهای موضوعی : پلیمر
Hamed Asadi
1
(Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran.)
Hossein Anaraki-Ardakani
2
(Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran.)
Parviz Torabi
3
(Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran.)
Narges Taheri
4
(Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran.)
کلید واژه:
چکیده مقاله :
An efficient and green protocol for synthesis of title compounds has been achieved via a one pot, three component reaction of 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one, aryl glyoxals and amides in choline chloride/oxalic acid as a deep eutectic solvent (DES) has been described. The DES system offers advantages in terms of environmentally benign, biodegradable, short reaction times, high yield and the use of safe and inexpensive components. DES can be easily recovered and can be reused for other runs without any reduction in the activity.
[1]. Y. J. Huang, F. Y. Yang and C. J. Zhu, J. Am. Chem. Soc., 127, 16387 (2005).
[2]. R. W. Armstrong, A. P. Combs, P. A.Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res.,
29, 123 (1996).
[3]. R. D. H. Murray, Nat. Prod. Rep., 12, 477 (1995).
[4]. A. Lacy and R. O’Kennedy, Curr. Pharm. Des., 10, 3797 (2004).
[5]. D. Guilet, D. Guilet, J. J. Hélesbeux, D. Séraphin, T. Sévenet, P. Richomme , J. J. Bruneton,
Nat. Prod., 64, 563 (2001) .
[6]. S. Emami and S. Dadashpour, Eur J. Med. Che., 102, 611 (2015).
[7]. Y. Cui, C. Li, J. Yin, S. Li, Y. Jia, M. Bao, J. Mol. Liq., 236,338 (2017).
[8]. Q. Zhang, K. De. Oliveira Vigier, S. Royer, F. Jerome, Chem. Soc. Rev., 41, 7108 (2012).
[9]. N. Azizi, T. Soleymani Ahooi, M. Mahmoudi Hashemi , Journal of Molecular Liquids, 246,
221 (2017).
[10]. M. Francisco, A. Van den Bruinhorst , M. C. Kroon, Angew Chem Int Ed., 52, 3074 (2013).
[11]. A. Shaabani, S. E. Hooshmand, A. T. Tabatabaei , Tetrahedron Lett,.57, 351 (2016).
[12] H. R. Lobo, B. S. Singh, G. S. Shankarling, Catal. Commun., 27, 179 (2012).
[13] A. Shaabani, S. E. Hooshmand, A. Tavousi Tabatabaei, Tetrahedron Lett. 57, 351 (2016).
[14] A. K. Sanap, G. S. Shankarling, RSC Adv., 4, 34938 (2014).
[15] A. P. Abbott, R. C. Harris, K. S. Ryder, C. D’Agostino, L. F. Gladden, M. D. Mantle, Green
Chem. 13, 82 (2011).
[16] S. Khandelwal, Y. K. Tailor, M. Kumar, J. Mol. Liq., 215, 345 (2016).
[17] E. L. Smith, A. P. Abbott, K. S. Ryder, Chem. Rev., 114, 11060(2014).
[18] M. Bakavoli, H. Eshghi, M. Rahimizadeh, M. R. Housaindokht, A. Mohammadi, H.
Monhemi, Res. Chem. Intermed., 41, 3497 (2015).
[19]. S. Khodabakhshi and B. Karami, Tetrahedron Letters, 55, 7136 (2014).
[20]. S. Khodabakhshi, B. Karami and K. Eskandari, Res. Chem. Intermed., 41, 7263(2015).
[21]. S. Khodabakhshi, M. Khaleghi Abbasabadi, M. Baghrnejad and F. Marahel, J. Chin. Chem.
Soc., 62, 9 (2015).
[22]. S. Khodabakhshi, M. Khaleghi Abbasabadi, S. Heydarian, S. Gharehzadeh Shirazi, F.
Marahel, Letters in Organic Chemistry, 12,465 (2015).
[23]. M. Arfavi-Safari, H. Anaraki-Ardakani, R. Badri, E. Tahanpesar, Journal of Applied Chemical
Research, 13, 3, 27 (2019).
[24]. H. Anaraki-Ardakani, M. H. Mosslemin, M. Anary-Abbasinejad, N. Shams, S. H.
Mirhosseini, Arkivoc xi, 343 (2010).
[25]. H. Anaraki-Ardakani, M. Noei and A.Tabarzad, Chinese Chemical Letters, 23, 45 (2012).
[26]. H. Asai, H.Anaraki-Ardakani,P. Torabi , N.Taheri, Rev. Roum. Chim., 65(9), 795 (2020).
[27]. M. Arfavi-Safari, H. Anaraki-Ardakani, R. Badri, E. Tahanpesar, Journal of Chemical
Research, 41, 6, 321 (2017).
[28]. B. Khalili, P. Jajarmi, B. Eftekhari-Sis and M. M. Hashemi, J. Org. Chem., 73, 2090 (2008).
[29]. A. P. Abbott, D. Boothby, G. Capper, D. L. Davies, R. K. Rasheed , J. Am. Chem. Soc.,
126, 9142 (2004).
[30]. A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed, V. Tambyrajah, Chem. Commun.,
70(2003).