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Letters in Organic Chemistry

Author(s): Elham Moosazadeh, Enayatollah Sheikhhosseini*, Dadkhoda Ghazanfari and Shahla Soltaninejad

DOI: 10.2174/1570178616666181203145211

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Uncatalyzed Synthesis of New Antibacterial Bisarylidene Meldrum's Acid Derivatives Functionalized with Ether Groups

Page: [818 - 824] Pages: 7

  • * (Excluding Mailing and Handling)

Abstract

A series of new bisarylidene Meldrum’s acid derivatives (3a-i) were prepared in high yield by a condensation reaction between Meldrum's acid and ether functionalized dibenzaldehyde, without any catalyst. Regardless of the nature of the substitution, all the reactions were completed within 2-3 hours in ethanol at reflux condition. In the reactions, the column purification of the products was not needed. The FT-IR, 1H-NMR, 13C-NMR and mass spectra confirm the structure of the products. Furthermore, the antibacterial activities of some synthesized compounds were investigated. According to the results, these compounds showed good activities against Staphylococcus aureus, Bacillus cereus, E. coli and Pseudomonas aeruginosa.

Keywords: Meldrum's acid, knoevenagel condensation, bisarylidene meldrum's acid, ethylene ether spacer, biological activity media, mass spectra.

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[1]
Razus, A.C.; Birzan, L.; Cristian, L.; Tecuceanu, V. Arkivoc, 2009, 11, 31-44.
[2]
Gao, S.; Tzeng, T.; Lan, Y.T.; Liu, J.T.; Yao, C.F. Arkivoc, 2009, 12, 347-361.
[3]
Chen, B.C. Hetrocycles, 1991, 32, 529-597.
[4]
Medien, H.A.A. Zeitschrift für Naturforschung B, 2014, 57, 1320-1326.
[5]
Nikoofar, K.; Shahedi, Y. Curr. Org. Chem., 2017, 21, 1098-1130.
[6]
Mieriņa, I.; Jure, M. Chem. Heterocycl. Compd., 2016, 52, 7-9.
[7]
Shaabani, A.; Hooshmand, S.E. RSC Advances, 2016, 6, 58142-58159.
[8]
Mokhtari, T.S.; Sheikhhosseini, E.; Amrollahi, M.A.; Sheibani, H. J. Saudi Chem. Soc., 2017, 21, 300-305.
[9]
Kraus, G.A.; Krolski, M.E. J. Org. Chem., 1986, 51, 3347-3350.
[10]
Huang, X.; Xie, L. Synth. Commun., 1986, 16, 1701-1707.
[11]
Yin, Z.; Yang, L.; Wu, L. J. Chem. Sci., 2013, 125, 601-606.
[12]
Pita, B.; Sotelo, E.; Suarez, M.; Ravina, E.; Ochoa, E.; Verdecia, Y.; Novoa, H.; Blaton, N.; Ranter, C.; Peeters, O.M. Tetrahedron, 2000, 56, 2473-2479.
[13]
Brown, R.C.F.; Eastwood, F.W.; Harrington, K.J. Aust. J. Chem., 1974, 27, 2373-2384.
[14]
Brown, R.C.F.; McMullen, G.L. Aust. J. Chem., 1974, 27, 2385-2391.
[15]
Yang, G-P.; He, X.; Yu, B.; Hu, C-W. Appl. Organomet. Chem., 2018, 32, 4532-4539.
[16]
Feng, X.; Yang, T.; He, X.; Yu, B.; Hu, C-W. Appl. Organomet. Chem., 2018, 32, 4314-4321.
[17]
Sheikhhosseini, E.; Balalaie, S.; Bigdeli, M. Iran. J. Pharm. Res., 2016, 15(3), 337-342.
[18]
Ouaddari, H.; Beqqour, D.; Bennazha, J. I-E, Amrani.; Albizane, A.; Solhy, A.; Varma, R.S. Sustainable Chemistry and Pharmacy, 2018, 10, 1-8.
[19]
Davidson, D.; Bernhard, S.A. J. Am. Chem. Soc., 1948, 70, 3426-3428.
[20]
Corey, E.J. J. Am. Chem. Soc., 1952, 74, 5897-5905.
[21]
Fildes, D.; Caignaert, V.; Villemin, D.; Jaffres, P.A. Green Chem., 2001, 3, 52-56.
[22]
Bandgar, B.P.; Uppalla, L.S.; Sadavarte, V.S.J. J. Chem. Research (S), 2002, 2002, 40-41.
[23]
Hu, Y.; Wei, P.; Huang, H.; Le, Z-G.; Chen, Z-C. Synth. Commun., 2005, 35, 2955-2960.
[24]
Mudhar, H.; Witty, A. Tetrahedron Lett., 2010, 51, 4972-4974.
[25]
Song, A.; Wang, X.; Lam, K.S. Tetrahedron Lett., 2003, 44, 1755-1758.
[26]
Rao, P.S.; Venkatratnam, R.V. Indian J. Chem. Sect. B, 1993, 32B, 484-486.
[27]
Ghosh, S.; Das, J.; Chattopadhyay, S. Tetrahedron Lett., 2011, 52, 2869-2872.
[28]
Bandgar, B.P.; Uppalla, L.S.; Kurule, D.S. Green Chem., 1999, 1, 243-245.
[29]
Thorat, M.T.; Jagdale, M.H.; Mane, R.M.; Salunkhe, M.M.; Wadagaonkar, P.P. Curr. Sci., 1987, 56, 771-772.
[30]
Bigi, F.; Carlonil, S.; Ferrari, L.; Maggi, R.; Mazzacani, A.; Sartori, G. Tetrahedron Lett., 2011, 42, 5203-5205.
[31]
Tietze, L.F.; Beifuss, U. In comprehensive organic synthesis, Trost, B.M.; Fleming, I.; Heathcock, C.H. Oxford,. 1991.
[32]
Hedge, J.A.; Kruse, K.W.; Snyder, H.R. J. Org. Chem., 1961, 26, 3166-3170.
[33]
Shlaes, D.E.; Projan, S.J.; Edwards, J.E. ASM News, 2004, 70, 275-281.
[34]
O’Shea, R.; Moser, H.E. J. Med. Chem., 2008, 51, 2871-2878.
[35]
Faryabi, M.; Sheikhhosseini, E. J. Iran. Chem. Soc., 2015, 12(3), 427-432.
[36]
Hosseini, H.; Sheikhhosseini, E.; Ghazanfari, D. Iran. J. Catal., 2016, 6, 121-125.
[37]
Sheikhhosseini, E.; Soltaninejad, S. Iran. J. Sci. Technol. Trans. A Sci., 2017.
[38]
Sheikhhosseini, E. J. Saudi Chem. Soc., 2018, 22, 337-342.
[39]
Kim, J.; Marshal, M.R.; Wie, C. J. Agric. Food Chem., 1995, 43, 2839-2485.