Efficient Synthesis of α-Oximinoketones using Carboxyl and Nitrite Functionalized Graphene Quantum Dots: Dual role of Nanostructure as a Catalyst and Reagent
DOI:
https://doi.org/10.24297/jac.v12i6.6098Keywords:
Carboxyl and nitrite functionalized graphene quantum dotsAbstract
Carboxyl and nitrite functionalized graphene quantum dots (CNGQDs) was used for the efficient synthesis of α-oximinoketones under free mineral acid conditions at room temperature. CNGQDs was prepared via o-nitrozation of carboxyl and hydroxyl graphene quantum dots (CHGQDs) and used as a nitrosonium source and also as an efficient acidic catalyst for the synthesis of α-oximinoketones. The structure of the catalyst was characterized by FT-IR, XRD, TGA and photoluminescence techniques. The structures of the synthesized products were confirmed by FT-IR, 1H-NMR and 13C-NMR spectroscopic techniques. Stability and recyclability of the prepared homogeneous catalyst was studied in details. Reaction times and yields of the products were compared with previous reported methods resulting high yields and also shorter reaction times.
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References
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[2] Benoit, R., Sauter, H. and Kirstgen, R. Eur. Pat. Appl. Ep. 1992, 188, 498.
[3] Misslitz, U., Meyer, N. and Kast, J. Ger. Offen. DE 4. 1991, 18, 623.
[4] Mohan, R. R. 1991. Synthesis of thiazolidinyl-benzylidene/methyl benzylidene-hydrazides and their Mannich bases as CNS active and anti-inflammatory agents. Indian Drugs. 29 (1991), 120-122.
[5] Plate, R. Eur. Pat. Appl. Ep. 1993, 279, 559.
[6] Lazarevski, G. and Djokic, S. Eur. Pat. Appl. Ep. 1991, 35, 448.
[7] McOmie, J. F. W. 1973. Protective Groups in Organic Chemistry, vol. 46, Plenum Press, London, New York.
[8] Huang, L., Cheng, K., Yao, B., Xie, Y. and Zhang, Y. 2011. Iron-promoted C-C bond cleavage of 1,3-diketones: A route to 1,2-diketones under mild reaction conditions. J. Org. Chem. 76 (Jun, 2011), 5732-5737.
[9] Weissermer, K. and Arpe, H. J. 1978. Industrial Organic Chemistry, Springer Verlag, p.222.
[10] Cameron, M., Gowenlock, B. G. and Boyed, A. S. F. 1996. Studies in nitrosopyrazoles. Part 1. Preparative and spectroscopic studies of some 3,5-dialkyl-4-nitrosopyrazoles. J. Chem. Soc. Perkin. Trans. 2. (1996), 2271-2274.
[11] Ren, R. X. and Ou, W. 2001. Preparation of cyclic ketoximes using aqueous hydroxylamine in ionic liquids. Tetrahedron Lett. 42 (Nov, 2001), 8445-8446.
[12] Zolfigol, M. A. 2001. An efficient and chemoselective method for oximination of β-diketones under mild and heterogeneous conditions. Molecules. 6 (Jul, 2001), 694-698.
[13] Hajipour, A. R., Mohammadpoor-Baltrok, I., Nikbaghat, K. and Imanzadeh, G. 1999. Solid-phase synthesis of oximes. Synth. Comm. 29 (May, 1999), 1697-1701.
[14] Sharghi, H. and Sarvari, M. H. 2000. A mild and versatile method for the preparation of oximes by use of calcium oxide 1. J. Chem. Research (S). (Oct, 2000), 24-25.
[15] Valizadeh, H., Shomali, A. and Gholipour, H. 2012. Nitrite ionic liquids (IL-ONO and [bmim]NO2) as effective nitrosonium sources for the synthesis of α-oximinoketones under mild heterogeneous conditions. Chin. J. Chem. 30 (Jul, 2012), 163-166.
[16] Welsher, K., Liu, Z., Daranciang, D. and Dai, H. 2008. Selective probing and imaging of cells with single walled carbon nanotubes as near-infrared fluorescent molecules. Nano Lett. 8 (Jan, 2008), 586-590.
[17] (a) Liu, R., Wu, D., Liu, S., Koynov, K., Knoll, W. and Li, Q. 2009. An aqueous route to multicolor photoluminescent carbon dots using silica spheres as carriers. Angew. Chem. 121 (2009), 4668. (b) Liu, R.; Wu, D.; Liu, S.; Koynov, K.; Knoll, W.; Li, Q. 2009. An Aaueous route to multicolor photoluminescent carbon dots using silica spheres as carriers. Angew. Chem. Int. Ed. 48 (Apr, 2009), 4598-4601.
[18] Zhu, H., Wang, X., Li, Y., Wang, Z., Yang, F. and Yang, X. 2009. Microwave synthesis of fluorescent carbon nanoparticles with electrochemiluminescence properties. Chem. Commun. (Jul, 2009), 5118-5120.
[19] Yang, S. T., Wang, X., Wang, H. F., Lu, F. S., Luo, P. J. G., Cao, L., Meziani, M. J., Liu, J. H., Liu, Y., Chen, M., Huang, Y. and Sun, Y. P. 2009. Carbon dots as nontoxic and high-performance fluorescence imaging agents. J. Phys. Chem. C. 113 (Sept, 2009), 18110-18114.
[20] Zhao, Q. L., Zhang, Z. L., Huang, B. H., Peng, J., Zhang, M. and Pang, D. W. 2008. Facile preparation of low cytotoxicity fluorescent carbon nanocrystals by electrooxidation of graphite. Chem. Commun. (Sept, 2008), 5116-5118.
[21] Cao, L., Wang, X., Meziani, M. J., Lu, F., Wang, H., Luo, P. G., Lin, Y., Harruff, B. A., Veca, L. M., Murray, D., Xie, S. Y. and Sun, Y. P. 2007. Carbon dots for multiphoton bioimaging. J. Am. Chem. Soc. 129 (Aug, 2007), 11318-11319.
[22] Zheng, L. Y., Chi, Y. W., Dong, Y. Q., Lin, J. P. and Wang, B. B. 2009. Electrochemiluminescence of eater-soluble carbon nanocrystals released slectrochemically from Graphite. J. Am. Chem. Soc. 131 (Mar, 2009), 4564-4565.
[23] Pan, D., Guo, L., Zhang, J., Xi, C., Xue, Q. H., Huang, J. and et al. 2012. Cutting sp2clusters in graphene sheets into colloidal graphene quantum dots with strong green fluorescence. J. Mater. Chem. 22 (Jan, 2012), 3314-3318.
[24] Shomali, A., Valizadeh, H., Banan, A. and Mohammad-Rezaei, R. 2015. Efficient synthesis of Xanthene derivatives using carboxyl functionalized graphene quantum dots as an acidic nano-catalyst under microwave irradiation. RSC Advances. 5 (Oct, 2015), 88202-88208.
[25] Valizadeh, H., Shomali, A., Nourshargh, S. and Mohammad-Rezaei, R. 2015. Carboxyl and nitrite functionalized graphene quantum dots as a highly active reagent and catalyst for rapid diazotization reaction and synthesis of azo-dyes under solventfree conditions. Dyes and Pigments. 113 (Sept, 2015), 522-528.
[26] Kelly, K. F. and Billups, W. E. 2013. Synthesis of Soluble Graphite and Graphene. Accounts of Chemical Research. 46 (Nov, 2013), 4-13.
[27] Pan, D., Zhang, J., Li, Z. and Wu, M. 2010. Hydrothermal route for cutting graphene sheets into blue-luminescent graphene quantum dots. Adv Mater. 22 (Feb, 2010), 734-738.
[28] Mohammed, A. H. A. and Nagendrappa, G. 2003. A remarkably simple -oximation of ketones to 1,2-dione monooximes using the chlorotrimethylsilane–isoamyl nitrite combination. Tetrahedron Lett. 44 (Mar, 2003), 2753-2755.
[29] Ferris, A. 1959. Communications- α-oximino ketones. I. The "normal" and "abnormal" beckmann rearrangements. J. Org. Chem. 24 (Apr, 1959), 580-581.
[30] Zolfigol, M. A. and Choghamarani, A. G. 2003. Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the chemoselective α-nitrosation of β-diketones under mild conditions. Phosphorus, Sulfur, and Silicon. 178 (Oct, 2003), 1623-1629.
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Published
2017-04-25
How to Cite
Shomali, A., & Valizadeh, H. (2017). Efficient Synthesis of α-Oximinoketones using Carboxyl and Nitrite Functionalized Graphene Quantum Dots: Dual role of Nanostructure as a Catalyst and Reagent. JOURNAL OF ADVANCES IN CHEMISTRY, 12(6), 4089–4096. https://doi.org/10.24297/jac.v12i6.6098
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