Electrogenerated based-promoted synthesis of nanoparticles 5 benzoyl 4 (aryl) 2 hydroxy 6 trifluoromethyl 1,4 dihydro py-ridine 3 carbonitriles by three-component condensation of aryl aldehydes, malononitrile and 4,4,4 trifluoro 1 phenylbuta 1,3 dione

Esmaeil Goodarzi, Behrooz Mirza

Abstract


An electrochemical strategy to the synthesis of novel 5-benzoyl-4-(a­ryl)-2-hydroxy-6-trifluoromethyl-1,4-dihydro-pyridine-3-carbonitriles nano­par­ti­cles via three-component reaction of aryl aldehydes, malononitrile and 4,4,4-tri­fluoro-1-phenylbuta-1,3-dione in water/ethanol in an undivided cell in the present of sodium bromide as an electrolyte is described. This method has several advantages such as high to excellent product yields (65–85 %), atom economy, environment friendly, and no need for chromatographic separations.


Keywords


phenylbuta-1,3-dione in water/ethanol in an undivided cell in the present of sodium bromide as an electrolyte is described. This method has several advantages such as high to excellent product yields (65–85 %), atom economy, environment friendly, and no n

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References


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

H. Bienayme, C. Hulme, G. Oddon, P. Schmidt, Chem. sEur. J. 6 (2000) 3321 (https://dx.doi.org/10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A).

A. J. Von Wangelin, H. Neumann, D. Go¨rdes, S. Klaus, D, Stru¨bing, M. Beller, Chem.sEur. J. 9 (2003) 4286 (https://dx.doi.org/ 10.1002/chem.200305048)

R. V. A. Orru, M. de Greef, Synthesis, (2003) 1471 (https://dx.doi.org/ 10.1055/s-2003-40507)

M. N. Elinson, A. S. Dorofeev, F. M. Miloserdov G. I. Nikishin, Mol. Divers. 13 (2009) 47 (https://dx.doi.org/ 10.1007/s11030-008-9100-1)

M. N. Elinson, A. I. Ilovsaiky, A. S. Dorofeev, V. M. Merkulova, N. O. Stepanov, F. M. Miloserdov, Y. N. Ogibin, G. I. Nikishin, Tetrahedron 63 (2007) 10543 (https://dx.doi.org/10.1016/j.tet.2007.07.080)

L. Wang, J. Gao, L. Wan, Y. Wang,C. Yao, Res. Chem. Intermediat 41 (2015) 2775 (https://dx.doi.org/10.1007/s11164-013-1387-6)

M. N. Elinson, A. S. Dorofeev, F. M. Miloserdov, A. I. Ilovaisky, S. K. Feducovich, P. A. Belyakov, G. I. Nikishin, Adv. Synth. Catal. 350 (2008) 591 (https://dx.doi.org/ 10.1007/s11030-009-9207-z)

S. Makarem, A. R. Fakhari, A. A. Mohammadi, Ind. Eng. Chem. Res. 5 (2012) 2200 (https://dx.doi.org/10.1021/ie200997b)

F. Bossert, H. Meyer, E.Wehinger, Angew. Chem. Int. Ed. Engl. 20 (1981) 762 (https://dx.doi.org/10.1002/anie.198107621)

R. Mannhol, B. Jablonk, W. Voigdt, K. Schoenafinger, K. Schrava, Eur. J. Med. Chem. 27 (1992) 229 (https://dx.doi.org/10.1016/0223-5234(92)90006-M)

G. L. Reid, P. A. Meredith, F. Pasanisi, J. Cardiovasc. Pharmacol. 7 (1985) S18 (https://journals.lww.com/cardiovascularpharm/Abstract/1985/07004/Clinical_Pharmacological_Aspects_of_Calcium.4.aspx)

R. Shan, C. Velazquez, E. Knaus, J. Med. Chem. 47 (2004) 254 (https://dx.doi.org/ 10.1021/jm030333h)

M. Kawase, A. Shah, H. Gaveriya, N. Motohashi, H. Sakagami, A. Varga, J. Molnar. Bioorg. Med. Chem. 10 (2002)1051 (https://dx.doi.org/10.1016/S0968-0896(01)00363-7)

T. Hiyama, Organofluorine Compounds, Springer–Verlag, Berlin, 2000 (https://dx.doi.org/10.1007/978-3-662-04164-2)

J. T. Welch, S. Eswarakrishnan (Eds.), Fluorine in Bioorganic Chemistry, Wiley, New York, 1991 (https://dx.doi.org/10.1002/recl.19911100913)

J. Prabhakaran, M. D. Underwood, R. V. Parsey, V. Arango, V. J. Majo, N. R. Simpson, R. V. Heertum, J. J. Mann, J. S. D. Kumar, Biorg. Med. Chem. 15 (2007) 1802 (https://dx.doi.org/10.1016/j.bmc.2006.11.033).

X. Liu, C. Xu, M. Wang, Q. Liu, Chem. Rev. 115 (2015) 683 (https://dx.doi.org/10.1021/cr400473a)

R. Dey, S. Sultana, B. Bishayi, J. Neuroimmunol. 316 (2018) 23 (https://dx.doi.org/10.1016/j.jneuroim.2017.12.006)

G. Russo, G. M. Paganotti, S. Soeria-Atmadja, M. Haverkamp, D. Ramogola-Masire, V. Vullo, L. L. Gustafsson, Infect. Genet. Evol. 192 (2016) 207 (https://dx.doi.org/10.1016/j.meegid.2015.11.014)

K. J. Palmer, S. M. Holliday, R. N. Brogden, Drugs. 1993 (1993) 430 (https://dx.doi.org/10.2165/00003495-199345030-00009)

J. Hasskarl, Recent Results in Cancer Res. 201 (2014) 145 (ISSN: 0080-0015)

T. Mohaddeseh, B. Mirza, M. Zeeb, Journal of Nanostructure in Chemistry 8 (2018) 421 (https://dx.doi.org/10.1007/s40097-018-0282-5)

G. Esmaeil, B. Mirza, Journal of Chemical Research 10 (2018) 521 (https://dx.doi.org/10.3184/174751918X15385231933446).

Z. M. Darvish, B. Mirza,S. Makarem, J. Heterocyclic Chem. 54 (2017) 1763 (https://doi.org/10.1002/jhet.2755)

D. Nematollahi, J. Azizian, M. Сargordan-Arani, M. Hesari, S. Јameh-Bozorghi, A. Alizadeh, L. Fotohi, B. Mirza, Chem. Pharm. Bull. 56 (2008) 1562 (https://dx.doi.org/10.1248/cpb.56.1562)

S. Makarem, A. R. Fakhari, A. A. Mohammadi, Ind. Eng. Chem. Res. 51 (2012) 2200 (https://dx.doi.org/10.1021/ie200997b)

S. Makarem; B. Mirza; Z. Mohammad Darvish; N. Amiri Notash; S. Ashrafi, Anal. Bioanal. Chem. Res. 6 (2019) 231 (https://dx.doi.org/10.22036/abcr.2018.142244.1230).




DOI: https://doi.org/10.2298/JSC190316063G

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