Electrogenerated base-promoted synthesis of 4-aryl-5-benzoyl-2-hydroxy-6-(trifluoromethyl)-1,4-dihydropy¬ridine-3-carbonitriles nanoparticles by three-component condensation of aromatic aldehydes, malononitrile and 4,4,4-trifluoro-1-phenylbutane-1,3-dione

Esmaeil Goodarzi, Behrooz Mirza

Abstract


An electrochemical strategy to the synthesis of novel 4-aryl-5-ben­zoyl-2-hydroxy-6-(trifluoromethyl)-1,4-dihydropyridine-3-carbonitriles nano­par­ti­cles via three-component reaction of aromatic aldehydes, malononitrile and 4,4,4-tri­fluoro-1-phenylbutane-1,3-dione in water/ethanol in an undivided cell in the presence 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


multi-component; electrosynthesis; 1,4-dihydropyridine; nano¬sized; aromatic aldehydes

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. Eur. 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. Gördes, S. Klaus, D. Strübing, M. Beller, Chem. Eur. 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. Diversity 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. Intermed. 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. 51 (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, in Organofluorine Compounds, H. Yamamoto, Ed., Springer Verlag, Berlin, 2000, p. 137 (https://dx.doi.org/10.1007/978-3-662-04164-2)

Fluorine in Bioorganic Chemistry, J. T. Welch, S. Eswarakrishnan, Eds., Wiley, New York, 1991

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 Cancer Res. 201 (2014) 145 (ISSN: 0080-0015)

T. Mohaddeseh, B. Mirza, M. Zeeb, J. Nanostruct. Chem. 8 (2018) 421 (https://dx.doi.org/10.1007/s40097-018-0282-5)

G. Esmaeil, B. Mirza, J. Chem. Res. 42 (2018) 521 (https://dx.doi.org/10.3184/174751918X15385231933446).

Z. M. Darvish, B. Mirza, S. Makarem, J. Heterocycl. 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, 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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