A novel application of Co3O4@SiO2 nanocomposite as an efficient and robust catalyst for the preparation of some imidazolone derivatives

Document Type: Research Paper

Authors

Department of Chemistry, Qom Branch, Islamic Azad University, Qom, PO Box 37491-13191, Iran

Abstract

In the present work, a simple, green and efficient procedure for the synthesis of imidazolone derivatives is described via the reaction of oxazolones and different arylamines in the presence of Co3O4@SiO2 nanocomposite as a catalyst under solvent-free conditions at 90°C. The catalyst has been fully analyzed by FT-IR, FE-SEM, EDX, and XRD analysis. The present method offers several advantages such as high yields, short reaction times, mild reaction conditions and recoverability of the catalyst. In addition, the obtained heterocyclic compounds were analyzed by FT-IR and 1HNMR spectroscopy analysis.

Graphical Abstract

A novel application of Co3O4@SiO2 nanocomposite as an efficient and robust catalyst for the preparation of some imidazolone derivatives

Highlights

  • An efficient synthesis of imidazolone by Co3O4@SiO2
  • Characterization of the catalyst by FT-IR, FE-SEM, EDX, VSM and XRD analysis
  • The main advantages were high yields, short reaction times, and reusability of the catalyst.

Keywords


[1] S. Renault, S. Bertrand, F. Carreaux, J.P. Bazureau, Parallel solution-phase synthesis of 2-alkylthio-5-arylidene-3,5-dihydro-4H-imidazol-4-one by one-pot three-component domino reaction, J. Combin. Chem. 9 (2007) 935-942.
[2] M. Nematpour, S.R. Koohi, E. Abedi, M. Lotfi, A green, one-pot formation of imidazolone and pyrimidinone derivatives containing a sulfonyl group, J. Chem. Res. 40 (2016) 652-654.
[3] D. Djukanovic, M. Petkovic, M. Simic, P. Jovanovic, G. Tasic, V. Savic, Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot, domino dehydration/base promoted cyclisation process, Tetrahedron Lett. 59 (2018) 914-917.
[4] S.O. Zaitseva, S.V. Golodukhina, N.S. Baleeva, E.A. Levina, A.Y. Smirnov, M.B. Zagudaylova, M.S. Baranov, Azidoacetic acid amides in the synthesis of substituted arylidene-1-h-imidazol-5-(4h)-ones, ChemistrySelect, 3 (2018) 8593-8596.
[5] D.E. Demong, I. Ng, M.W. Miller, A.W. Stamford, A novel method for the preparation of 4-arylimidazolones, Org Lett. 15 (2013) 2830-2833.
[6] H. Joshi, P. Upadhyay, D. Karia, A.J. Baxi, Synthesis of some novel imidazolinones as potent anticonvulsant agents, Eur. J. Med. Chem. 38 (2003) 837-840.
[7] K.R. Olsen, A.J. Kolar, N-acylimines as intermediates in reactions of α-substituted α-amino acids and dehyroamino acids, Tetrahedron Lett. 16 (1975) 3579-3582.
[8] M. Goodman, C.B. Glaser, Formation and reactions of amino acids and peptide oxazolones, Tetrahedron Lett. 10 (1969) 3473-3475.
[9] D. Beaufils, G. Danger, L. Boiteau, J.C. Rossia, R. Pascal, Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings, Chem. Commun. 50 (2014) 3100-3102.
[10] S. Fozooni, M.A. Tikdari, H. Hamidian, H. Khabazzadeha, A synthesis of some new 4-arylidene-5(4H)-oxazolone azo dyes and an evaluation of their solvatochromic behaviour, Arkivoc, XIV (2008) 115-123.
[11] G.O. Urut, S. Alp, D. Topkaya, Synthesis, spectral, and thermal properties of some phosphorus-containing 9,10-anthraquininoid, thermally stable dyes, Dyes and Pigments, 145 (2017) 103-111.

[12] N.B. Patel, H.R. Patel, Synthesis and antibacterial and antifungal studies of novel nitrogen containing heterocycles from 5-ethylpyridin-2-ethanol, Indian J. Pharm. Sci. 72 (2010) 613-620.
[13] N.B. Patel, H.R. Patel, Design and synthesis of new imidazolinone derivatives as potential antifungal agents, J. Heterocyclic Chem. 48 (2011) 373-380.
[14] H. Lehr, S. Karlan, M.W. Goldberg, Derivatives of 4(5H)-imidazolone, J. Am. Chem. Soc. 75 (1953) 3640-3645.
[15] S. Fozooni, H. Khoshdast, H. Hassani, H. Hamidian, Synthesis of oxazolone and imidazolone derivatives in presence of H2O2 promoted fly ash as a novel and efficient catalyst, J. Sci. I. R. Iran, 28 (2017) 221-230.
[16] L.D. Luca, Naturally occurring and synthetic imidazoles: Their chemistry and their biological activities, Curr. Med. Chem. 13 (2006) 1-23.
[17] P.T. Oskoie, Y. Mansoori, Fe3O4@ZrO2-SO3H Nanoparticles: A new magnetically retrievable catalyst for esterification of mono- and dicarboxylic acids, J. Particle Sci. Techol. 4 (2018) 1-12.
[18] C.J. Jia, M. Schwickardi, C. Weidenthaler, W. Schmidt, S.B. Korhonen, M. Weckhuysen, F. Schüth, Co3O4-SiO2 Nanocomposite: A very active catalyst for co oxidation with unusual catalytic behavior, J. Am. Chem. Soc. 133 (2011) 11279-11288.
[19] G.A. M. Ali, O.A. Fouad, S.A. Makhlouf, M.M. Yusoff, K.F. Chong, Co3O4/SiO2 nanocomposites for supercapacitor application, J. Solid State Electr. 18 (2014) 2505-2512.
[20] J. Dong, L. Song, J.J. Yin, W. He, Y. Wu, N. Gu, Y. Zhang, Co3O4 nanoparticles with multi-enzyme activities and their application in immunohistochemical assay, ACS. Appl. Mater. Interf. 6 (2014) 1959-1970.
[21] M. Sivachidambaram, J.J. Vijaya, K. Kaviyarasu, L.J. Kennedy, H.A. Al-Lohedane, R.J. Ramalingam, A novel synthesis protocol for Co3O4 nanocatalystsand their catalytic applications, RSC Adv. 7 (2017) 38861-38870. 

[22] S. Bazgir, S. Farhadi, Microwave-assisted rapid synthesis of Co3O4 nanorods from CoC2O4.2H2O nanorods and its application in photocatalytic degradation of methylene blue under visible light irradiation, Int. J. Nano Dimens. 8 (2017) 284-297.
[23] C. Qian, X. Guo, W. Zhang, H. Yang, Y. Qian, F. Xu, S. Qian, S. Lin, T. Fan, Co3O4 nanoparticles on porous bio-carbon substrate as catalyst for oxygen reduction reaction, Micropor. Mesopor. Mat. 277 (2019) 45-51.
[24] M.A. Ghasemzadeh, M.H. Abdollahi-Basir, Z. Elyasi, Synthesis of some novel imidazoles catalyzed by Co3O4 nanoparticles and evaluation of their antibacterial activities, Comb. Chem. High T. Scr. 21 (2018) 271-280.
[25] M.A. Ghasemzadeh, B. Molaei, M.H. Abdollahi-Basir, F. Zamani, Preparation and catalytic study on a novel amino-functionalized silica-coated cobalt oxide nanocomposite for the synthesis of some indazoles, Acta Chim. Slov. 64 (2017) 73-82.
[26] R. Suthakaran, S. Kavimani, P. Venkaiaiah, K. Suganthi, Synthesis and antimicrobial activity of 3-(2-(4z)-4-substituted benzylidene-4,5-dihydro-5-oxo-2-phenyl imidazol-1-yl)ethyl)-6,8-un/dibromo subtituted-2-substituted quinazoline-(3h)-one, Rasayan J. Chem. 1 (2008) 22-29.
[27] K.D. Hartlen, A.P.T. Athanasopoulos, V. Kitaev, Facile preparation of highly monodisperse small silica spheres (15 to >200 nm) suitable for colloidal templating and formation of ordered arrays, Langmuir, 24 (2008) 1714-1720.
[28] K. Azizi, M. Karimi, H.R. Shaterian, A. Heydari, Ultrasound irradiation for the green synthesis of chromenes using L-arginine-functionalized magnetic nanoparticles as a recyclable organocatalyst, RSC Adv. 4 (2015) 42220-42225.