Green and efficient synthesis of new β-amido-aroyl carbonyl derivatives catalyzed by choline chloride/urea as a deep eutectic solvent Scientific paper

Main Article Content

Anita Berjis
https://orcid.org/0000-0001-8002-6232
Behroox Mirza
https://orcid.org/0000-0002-1334-9418
Hossein Anaraki-Ardakani
https://orcid.org/0000-0002-0512-8033

Abstract

A green and highly efficient synthesis of some new β-amido-aroyl carbonyl derivatives has been achieved through a one-pot, three-component reaction of dimedone/barbituric acid derivatives, arylglyoxals, and amides in choline chloride/urea as a deep eutectic solvent (DES). The use of biode­grad­able materials, short reaction time and high yields of products introduced this protocol as an efficient environmentally friendly method. The DES could be easily recovered and reused about four times with satisfied catalytic activity.

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How to Cite
[1]
A. Berjis, B. Mirza, and H. Anaraki-Ardakani, “Green and efficient synthesis of new β-amido-aroyl carbonyl derivatives catalyzed by choline chloride/urea as a deep eutectic solvent: Scientific paper”, J. Serb. Chem. Soc., vol. 86, no. 6, pp. 547-553, Jun. 2021.
Section
Organic Chemistry

References

B. M. Trost, Science 254 (1991) 1471 (https://doi.org/10.1126/science.1962206)

S. Pal, M. Nasim Khan, S. Karamthulla , L. H. Choudhury, Tetrahedron Lett. 56 (2015) 359 (https://doi.org/10.1016/j.tetlet.2014.11.095)

A. J. Von Wangelin, H. Neumann, D. Gördes, S. Klaus, D. Strübing , M. Beller, Chem. Eur. J. 9 (2003) 4286 (https://doi.10.1002/chem.200305048)

P. T. Anastas, Crit. Rev. Anal. Chem. 29 (1999) 167 (https://doi.org/10.1080/10408349891199356)

P. Liu, J. W. Hao, L. P. Mo, Z. H. Zhang. RSC Adv. 5 (2015) 48675 (https://doi.org/10.1039/c5ra05746a)

Y. Cui, C. Li, J. Yin, S. Li, Y. Jia, M. Bao. J. Mol. Liq. 236 (2017) 338 (https://doi.org/10.1016/i.gee.2019.03.002)

Q. Zhang, K. De.Oliveira Vigier, S. Royer, F. Jerome, Chem. Soc. Rev. 41 (2012) 7108 ( https://doi.org/10.1039/c2cs35178a)

N. Azizi, T. Soleymani Ahooi , M. Mahmoudi Hashemi, J. Mol. Liq. 246 (2017 ) 221 (https://doi.org/10.1016/j.molliq.2017.09.049)

P. Liu, J.-W. Hao, L.-P. Mo, Z.-H. Zhang. RSC Adv. 5 (2015) 48675 (https://doi.org/10.1039/c5ra05746a)

E. Habibi, K. Ghanemi, M. Fallah-Mehrjardi, A. Dadolahi-Sohrab, Anal. Chim. Acta 762 (2013) 61 (https://doi.10.1016/j.aca.2012.11.054)

A. Shaabani, S. E. Hooshmand, A. Tavousi Tabatabaei, Tetrahedron Lett. 57 (2016) 351 (https://doi.org/10.1016/j.tetlet.2015.12.017)

A. K. Sanap, G. S. Shankarling, RSC Adv. 4 (2014) 34938 (https://doi.org/10.1039/C4RA05858E)

A. P. Abbott, R. C. Harris, K. S. Ryder, C. D’Agostino, L. F. Gladden, M. D. Mantle, Green Chem. 13 (2011 ) 82 (https://doi.org/10.1039/C0GC00395F)

S. Khandelwal, Y. K. Tailor, M. Kumar, J. Mol. Liq. 215 (2016) 345 (https://doi.org/10.1016/j.molliq.2015.12.015)

E. L. Smith, A. P. Abbott, K. S. Ryder, Chem. Rev. 114 (2014) 11060 (https://doi.org/10.1021/cr.300162p)

J. Barluenga, B. Olano, S. Fustero, J. Org. Chem. 50 (1985) 4052 (https://doi.org/10.1021/jo00221a018)

I. Nageshwar Rao, E. N. Prabhakaran, S. Kumar Das, J. Iqbal, J. Org. Chem. 68 (2003) 4079 (https://doi.org/10.1021/jo020559c)

R. P. Cheng, S. H. Gellman, W. F. De. Grado, Chem. Rev. 101 (2001) 3219. (https://doi.org/10.1021/cr000045i)

U. Dahn, H. Hagenmaier, H. Hohne, W. A. König, G. Wolf, H. Zahner. Arch. Microbiol. 107 (1997) 143 (https://doi.org/10.1007/bf00446834)

R. M. Kumbhare, M. Sridhar, J. Chem. Sci. 124 (2012) 495 (https://doi.org/10.1007/s12039-011-0183-3)

G. L. Buchanan, Chem. Soc. Rev. 17 (1988) 91 (https://doi.org/10.1039/CS9881700091)

D. Bahulayan, S. K. Das, J. Iqbal, J. Org. Chem. 68 (2003) 5735 (https://doi.org/10.1021/jo02734p)

A. Javid, M. M. Heravi , F. F. Bamoharram, Monatsh. Chem. 143 (2012) 831 (https://doi.org/10.1007/s00706-011-0669-1)

24. R. Khoeiniha, A. Olyaei, M. Saraei, J. Heterocyclic Chem. 54 (2017) 1746 (https://doi.org/10.1002/jhet.2752)

O. N. Petrova1, L. L. Zamigajlo, K. S. Ostras, S. V. Shishkina, O. V. Shishkin, A. V. Borisov, V. I. Musatov1, M. G. Shirobokova, V. V. Lipson, Chem. Heterocycl. Comp. 51 (2015) 310 (https://doi.org/10.1007/s10593-015-1700-y)

F. Jafari, S. Kodabakhshi , S. Gharehzadeh Shirazi, RSC Adv. 4 (2014) 48095 (https://doi.org/10.1039/C4RA90049A)

S. Khodabakhshi, B. Karami, Tetrahedron Lett. 55 (2014) 7136 (https://doi.org/10.1016/j.tetlet.2014.11.016)

S. Khodabakhshi, M. Khaleghi Abbasabadi, M. Baghrnejad, F. Marahel, J. Chin. Chem. Soc. 62 (2015) 9 (https://doi.org/10.1002/jccs.201400266)

B. Khalili, P. Jajarmi, B. Eftekhari-Sis , M. M. Hashemi, J. Org. Chem. 73 (2008) 2090 (https:// doi.org/10.1021/jo702385n)

J. Khalafy, M. Ezzati, M. Rimaz, A.d Poursattar Marjani, H. Yaghoobnejad Asl, J. Iran. Chem. Soc. 11 (2014) 1067 (https://doi.org/10.1007/s13738-013-0378-2)

J. Khalafy, M. Rimaz, M. Ezzati, R. H. Prager, Bull. Korean Chem. Soc. 33 (2012) 9 (http://dx.doi.org/10.5012/bkcs.2012.33.9.2890)