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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Zeolite-encapsulated Mn(II) Complex: A New Nano Catalyst for the Synthesis of Modafinil and Its Derivatives

Author(s): Mohammad Javad Taghizadeh*, Huoman Karimi and Akbar Mirzaie

Volume 16, Issue 7, 2019

Page: [541 - 549] Pages: 9

DOI: 10.2174/1570178615666180622123944

Price: $65

Abstract

The Mn-hydrazone Schiff base encapsulated into NaY has been prepared and characterized as a new heterogeneous catalyst. Elemental analysis, UV-Vis, infrared spectroscopic analysis, diffused reflectance spectroscopy, thermal analysis, small angle X-ray diffraction, and N2 sorption demonstrate the existence of Mn-hydrazone schiff base in the nanopores of zeolite-Y. MnII(Hsal- hrz)/Y, which showed excellent catalytic property in oxidation with various sulfide compounds including important drugs such as adrafinil and modafinil, using hydroperoxide-urea (UHP) as oxidant. Thioanisole conversion was high (98%).

Keywords: Heterogeneous catalyst, sulfoxidation, adrafinil, modafinil, zeotite, hydrazone.

Graphical Abstract
[1]
Maurya, M.R.; Chandrakar, A.K.; Chand, S. J. Mol. Catal. A Chem., 2007, 263, 227-237.
[2]
Jin, C.; Fan, W.; Jia, Y.; Fan, B.; Ma, J. Li. R. J. Mol. Catal. A Chem., 2006, 249, 23-30.
[3]
Zhu, D.; Mei, F.; Chen, L.; Li, T.; Mo, W.; Li, G. Energy Fuels, 2009, 23, 2359-2363.
[4]
Modi, C.K.; Trivedi, P.M. Microporous Mesoporous Mater., 2012, 155, 227-232.
[5]
Baleizao, C.; Gigante, B.; Sabater, M.J.; Garcia, H.; Corma, A. Appl. Catal. A Gen., 2002, 228, 279-288.
[6]
Kim, G.J.; Park, D.W. Catal. Today, 2000, 63, 537-547.
[7]
Xiang, S.; Zhang, Y.; Xin, Q.; Li, C. Chem. Commun., 2002, 1, 2696-2697.
[8]
Peukert, S.; Jacobsen, E.N. Org. Lett., 1999, 1, 1245-1248.
[9]
Jia, M.; Seifert, A.; Thiel, W.R. J. Catal., 2004, 221, 319-324.
[10]
Sakthivel, A.; Zhao, J.; Hanzlik, M.; Chiang, A.S.T.; Herrmann, W.A.; Kuhn, F.E. Adv. Synth. Catal., 2005, 347, 473-483.
[11]
Zhao, J.Q.; Wang, W.Y.; Zhang, Y.C. J. Inorg. Organomet. Polym. Mater., 2008, 18, 441-446.
[12]
Kureshy, R.I.; Prathap, K.J.; Kumar, M.; Kumar, B.P.; Hasan Khan, N.; Abdi, S.H.R.; Bajaj, H.C. Tetrahedron, 2011, 67, 8300-8307.
[13]
Wang, B.; Wasielewski, M.R. J. Am. Chem. Soc., 1997, 119, 12-21.
[14]
Maity, N.C.; Abdi, S.H.R.; Kureshy, R.I.; Khan, N.H.; Suresh, E.; Dangi, G.P.; Bajaj, H.C. J. Catal., 2011, 277, 123-129.
[15]
Ready, J.M.; Jacobson, E.N. J. Am. Chem. Soc., 2001, 123, 2687-2688.
[16]
Kureshy, R.I.; Khan, N.H.; Abdi, S.H.R.; Vyas, A.P.; Singh, S.; Ahmad, I.; Jasra, R.V. J. Catal., 2004, 224, 229-235.
[17]
Banisafar, A.; LaDuca, R.L. Inorg. Chim. Acta, 2011, 373, 295-300.
[18]
Balkus, K.; Gabrielov, A.G.; Bell, S.L.; Bedioui, F.; Roue, L.; Devynck, J. Inorg. Chem., 1994, 33, 67-72.
[19]
Gabrielow, A.G.; Balkus, J.K.J.; Bell, S.L.; Bedioui, F.; Devynck, J. Microporous Mater., 1994, 2, 119-126.
[20]
Skrobot, F.C.; Rosa, I.L.V.; Marques, P.A.; Martins, P.R.; Rocha, J.; Valente, A.A.; Iamamoto, Y. J. Mol. Catal. A Chem., 2005, 237, 86-92.
[21]
Khan, T.A.; Hriljac, J.A. Inorg. Chim. Acta, 1999, 294, 179-182.
[22]
Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Moosavifar, M. J. Mol. Catal. A Chem., 2009, 302, 68-75.
[23]
Zhan, B.Z.; Li, X.Y. Chem. Commun., 1998, 3, 349-350.
[24]
Mostafa, S.I.; Ikeda, S.; Ohtani, B. J. Mol. Catal. A Chem., 2005, 225, 181-188.
[25]
Saha, P.K.; Dutta, B.S.; Jana, R.; Bera, S.; Saha, K.; Okamoto, S. Polyhedron, 2007, 26, 563-571.
[26]
Salama, T.M.; Ali, I.O.; Hanafy, A.I.; Al-Meligy, W.M. Mater. Chem. Phys., 2009, 113, 159-165.
[27]
Datta, A.; Karan, N.K.; Mitra, S.; Rosair, G. Nature, 2002, 57b, 999-1002.
[28]
Ouyang, X.M.; Fei, B.L.; Okamuro, T.A.; Sun, W.Y.; Tang, W.X.; Ueyama, N. Chem. Lett., 2002, 31, 362-363.
[29]
Gupta, K.C.; Sutar, A.K. Coord. Chem. Rev., 2008, 252, 1420-1450.
[30]
Bagherzadeh, M.; Zare, M. J. Sulfur Chem., 2011, 32, 335-343.
[31]
Bagherzadeh, M.; Latifi, R.; Tahsini, L.; Amani, V.; Ellern, A.; Woo, L.K. Polyhedron, 2009, 28, 2517-2521.
[32]
Ainscough, E.W.; Brodie, A.M.; Denny, W.A.; Finlay, G.J.; Gothe, S.A.; Ranford, J.D. J. Inorg. Biochem., 1999, 77, 125-133.
[33]
Melnyk, P.; Leroux, V.; Sergheraerta, C.; Grellier, P. Bioorg. Med. Chem. Lett., 2006, 16, 31-35.
[34]
Gravert, D.J.; Griffin, J.H. J. Org. Chem., 1993, 58, 820-825.
[35]
Vicini, P.; Zani, F.; Cozzini, P.; Doytchinova, I. Eur. J. Med. Chem., 2002, 37, 553-564.
[36]
Rollas, S.; Gulerman, N.; Erdeniz, H. Farmaco, 2002, 57, 171-174.
[37]
Iskander, M.F.; El-Sayed, L.; Salem, N.M.H.; Haase, W.; Linder, H.J.; Foro, S. Polyhedron, 2004, 23, 23-31.
[38]
Das, S.; Pal, S. J. Organomet. Chem., 2006, 691, 2575-2579.
[39]
Szklarzewicz, J.; Gruszewska, A. Transition Met. Chem, 2005, 30, 27-34.
[40]
Maurya, M.R.; Agarwal, S.; Bader, C.; Ebel, M.D. Rehder. Dalton Trans., 2005, 44, 537-544.
[41]
Bagherzadeh, M. Amini. M. Inorg. Chem. Commun., 2009, 12, 21-25.
[42]
Correa, R.J.; Salomao, G.C.; Olsen, M.H.N.; Cardozo, F.L.; Drago, V.C.; Fernandes, O.A.C. Appl. Catal. A, 2008, 336, 35-39.
[43]
Naskar, S.; Biswas, S.; Mishra, D.; Adhikary, B.; Falvello, L.R.; Soler, T.; Schwalbe, C.H.; Chattopadhyay, S.K. Inorg. Chim. Acta, 2004, 357, 4257-4264.
[44]
Ahmed, A.H.; Thabet, M.S. J. Mol. Struct., 2011, 1006, 527-535.
[45]
Quayle, W.H.; Peeters, G.; De Roy, G.L.; Vansant, E.F. Lunsford. J.H. Inorg. Chem., 1982, 21, 2226-2231.
[46]
Das, R.; Chakraborty, D. Tetrahedron Lett., 2010, 51, 6255-6258.

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