تبدیل تک ظرفی اپوکسیدها به 2 ، 1 دی استاتها در حضور نانوکاتالیست - مغناطیسی فریت کبالت تحت شرایط بدون حلال

نوع مقاله : مقاله پژوهشی

نویسنده

گروه شیمی، دانشگاه پیام نور، تهران

چکیده

در این پژوهش، نانوذرات مغناطیسی CoFe2O4 از طریق روش حالت جامد در داخل هاون چینی سنتز و سپس، در
دماهای بالا کلسینه شد. نانوفریت کبالت بهدست آمده با استفاده از روشهای XRD ، SEM ، FT-IR و VSM شناسایی و
بهعنوان کاتالیست در تبدیل تک ظرفی و مؤثر اپوکسیدهای متفاوت دارای استخلافهای آریلی، آلیلی و آلکیلی به 2،۱ دی -
استوکسی استرهای متناظر با استیک انیدرید در حمام روغن در دمای 70 درجه سانتیگراد و تحت شرایط بدون حلال استفاده شد.
سنتز 2،۱ دی استاتها در گسترهی زمانی - 4 - ۱ ساعت با بازده ۹5 - 77 درصد انجام شد. نانوکاتالیست مغناطیسی با استفاده از یک
آهنربای ساده به آسانی از محیط واکنش بازیافت شده و با حفظ ویژگی مغناطیسی و کاتالیستی در چرخه های بعدی مورد استفاده
دوباره قرار گرفت.

کلیدواژه‌ها


عنوان مقاله [English]

One-pot Conversion of Epoxides to 1,2-Diacetates in the presence of Cobalt Ferrite Magnetic Nanocatalyst under Solvent-free Conditions

نویسنده [English]

  • Ronak Eisavi
anTehr University, Noor Payame ,Science of Faculty ,Chemistry of Department,, Tehran
[1] K.G. Watson, Y. M. Fung, M. Gredley, G.J. Bird, W. R. Jackson, H. Gountzos, B. R. Matthews, “Asymmetric syntheses of (+)-diltiazem hydrochloride,” Journal of the Chemical Society, Chemical Communications, 15, 1018-1019, 1990.
[2] H.C. Kolb, K.B. Sharpless, “A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides,” Tetrahedron, 48, 10515-10530, 1992.
[3] F.A.J. Meskens, “Methods for the preparation of acetals from alcohols or oxiranes and carbonyl compounds,” Synthesis, 501-522, 1981.
[4] B.A.B. Prasad, G.V. Sekar, K. Sigh, “An efficient method for the cleavage of aziridines using hydroxyl compounds,” Tetrahedron Letters, 41, 4677-4679, 2000.
[5] M. Tokunaga, J.F. Larrow, F. Kakiuchi, E.N. Jacobsen, “Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis,” Science, 277, 936-938, 1997.
[6] R.H. Fan, X.L. Hou, “Tributylphosphine-catalyzed ring-opening reaction of epoxides and aziridines with acetic anhydride,” Tetrahedron Letters, 44, 4411-4413, 2003.
[7] A.B. Hughes, A. Rudge, “Deoxynojirimycin: synthesis and biological activity,” Natural Product Reports, 11, 135-162, 1994.
30 پاییز ۱۳۹۹ | شماره ۳ |سال هفتم
[8] V.H. Lillelund, H. H. Jensen, X.F. Liang, M. Bols, “Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin,” Chemical Reviews, 102, 515-554, 2002.
[9] F.A. Carey, R.J. Soundberg, “Advanced organic chemistry” Part B, Plenum Press, New York, 1997.
[10] S.S. Rana, J.J. Barlow, K.L. Matta, “The selective acetylation of primary alcohols in the presence of secondary alcohols in carbohydrates,” Tetrahedron Letters, 22, 5007-5010, 1981.
[11] J. Paust, “Recent progress in commercial retinoids and carotenoids,” Pure and Applied Chemistry, 63, 45-58, 1991.
[12] T. Yoshino, S. Inaba, H. Komura, Y. Ishido, “Synthetic studies with carbonates. Part 6. Syntheses of 2-hydroxyethyl derivatives by reactions of ethylene carbonate with carboxylic acids or heterocycles in the presence of tetraethylammonium halides or under autocatalytic conditions,” Journal of the Chemical Society, Perkin Transactions 1, 1266-1272, 1977.
[13] M.A. Rahman, B. Fraser-Reid, “Actinobolin via the anomeric effect,” Journal of the American Chemical Society, 107, 5576-5578, 1985.
[14] L.E. Tatarova, D.V. Korchagina, K.P. Volko, N. F. Salakhutdinov, V. A. Barkhash, Russ. “Reactions of epoxides prepared from some monoterpenes with acetic anhydride on aluminosilicate catalysts,” The Journal of Organic Chemistry, 39, 1076-1082, 2003.
[15] P. Ramesh, V.L. Niranjan Reddy, D. Venugopal, M. Subrahmanyam, Y. Venkateswarlu, “Zeolite-catalyzed ring-opening of epoxides to acetylated diols with acetic anhydride,” Synthetic Communications, 31, 2599-2604, 2001.
[16] R. Dalpozzo, A. De Nino, M. Nardi, B. Russo, A. Procopio, “1,2-Diacetates by epoxide ring-opening promoted by erbium(III) triflate,” Arkivoc, 6, 67-73, 2006.
[17] B. Das, V.S. Reddy, F. Tehseen, “A mild, rapid and highly regioselective ring-opening of epoxides and aziridines with acetic anhydride under solvent-free conditions using ammonium12-molybdophosphate,” Tetrahedron Letters, 47, 6865-6868, 2006.
[18] B. Yadollahi, F. Kabiri Esfahani, “Efficient preparation of vic-diacetates from epoxides and acetic anhydride in the presence of iron(III)-substituted polyoxometalate as catalyst,” Chemistry Letters, 36, 676-677, 2007.
[19] N. Azizi, B. Mirmashhori, M.R. Saidi, “Lithium perchlorate-promoted highly regioselective ring-opening of epoxides under solvent-free conditions,” Catalysis Communications, 8, 2198-2203, 2007.
[20] C.S. Swindell, B.P. Patel, “Stereoselective construction of the taxinine AB system through a novel tandem aldol-payne rearrangement annulations,” The Journal of Organic Chemistry, 55, 3-5, 1990.
[21] R.M. Evans, J.B. Fraser, L.N. Owen, “Dithiols. Part III. Derivatives of polyhydric alcohols,” Journal of the Chemical Society, 248-255, 1949.
[22] M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, L. Shariati, M. Babaghanbari, M. Zarea, “Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst
31 پاییز ۱۳۹۹ | شماره ۳ |سال هفتم
for ring-opening of epoxides,” Journal of the Iranian Chemical Society, 6, 789-799, 2009.
[23] B .Zeynizadeh, L. Sadighnia, “A green protocol for catalytic conversion of epoxides to 1,2-diacetoxy esters with phosphomolybdic acid alone or its supported on silica gel,” Bulletin of the Korean Chemical Society, 31, 2644-2648, 2010.
[24] H. Cavdar, N. Saracoglu, “Ring opening of epoxides with NaHSO4: Isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols,” Tetrahedron, 65, 985-989, 2009.
[25] S. Ali, R. Bittman, “Facile diacylation of glycidyl tosylate. Chiral synthesis of symmetricchain glycerophospholipids,” The Journal of Organic Chemistry, 53, 5547-5549, 1988.
[26] A. Gansauer, H. Bluhm, “Dramatic rate acceleration in titanocene catalyzed epoxide opening: cofactors and Lewis acid co-catalysis,” Chemical Communications, 19, 2143-2144, 1998.
[27] G. Sabitha, R. Satheesh Babu, M. Rajkumar, C. S. Reddy, J.S. Yadav, “Highly Regioselective Ring-opening of epoxides and aziridines using cerium(III) chloride,” Tetrahedron Letters, 42, 3955-3958, 2001.
[28] B. Zeynizadeh, L. Sadighnia, “One-pot catalytic conversion of epoxides to 1,2-diacetates with hydride transferring agents in acetic anhydride,” Synthetic Communications, 41, 637-644, 2011.
[29] M. Gilanizadeh, B. Zeynizadeh, “4Å molecular sieves catalyzed ring-opening of epoxides to 1,2-diacetates with acetic anhydride,” Current Chemistry Letters, 4, 153-158, 2015.
[30] M. Gilanizadeh, B. Zeynizadeh, “Direct transformation of epoxides to 1,2-diacetates with Ac2O/B(OH)3 system,” Journal of the Chemical Society of Pakistan, 37, 1234-1238, 2015.
[31] M. Gilanizadeh, B. Zeynizadeh, “Facile conversion of epoxides to 1,2-diacetates with NaOAc·3H2O/Ac2O system,” Iranian Journal of Chemistry and Chemical Engineering, 35, 25-29, 2016.
[32] M. Torabi Momen, F. Piri, R. Karimian, S. Parvin, “TiO2 (anatase) nanoparticles a novel catalyst for synthesis of vic-diacetates as biologically active compounds,” Journal of Applied Biotechnology Reports, 5, 26-31, 2018.
[33] S.T. Perri, S.N. Falling, “Process for the production of 1,2-bis(acyloxylates),” US Patent, 5,623,086, 1997.
[34] A.K. Gupta, M. Gupta, “Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications,” Biomaterials, 26, 3995-4021, 2005.
[35] Q.A. Pankhurst, J. Connolly, S.K. Jones, J. Dobson, “Applications of magnetic nanoparticles in biomedicine,” Journal of Physics D: Applied Physics, 36, R167-181, 2003.
[36] T. Neuberger, B. Schöpf, H. Hofmann, M. Hofmann, B. Rechenberg, “Superparamagnetic nanoparticles for biomedical applications: possibilities and limitations of a new drug delivery system,” Journal of Magnetism and Magnetic Materials, 293, 483-496, 2005.
[37] D.L. Graham, H.A. Ferreira, P.P. Freitas, “Magnetoresistive-based biosensors and biochips,” Trends in Biotechnology, 22, 455-462, 2004.
32 پاییز ۱۳۹۹ | شماره ۳ |سال هفتم
[38] A.‐H. Lu, E. L. Salabas, F. Schüth, “Magnetic nanoparticles: synthesis, protection, functionalization, and application,” Angewandte Chemie International Edition, 46, 1222-1244, 2007.
[39] S. Shylesh, V. Schünemann, W. R. Thiel, “Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis,” Angewandte Chemie International Edition, 49, 3428-3459, 2010.
[40] V. Polshettiwar, R.S. Varma, “Green chemistry by nano-catalysis,” Green Chemistry, 12, 743-754, 2010.
[41] R. Eisavi, S. Ghadernejad, B. Zeynizadeh, F. Mohammad Aminzadeh, “Magnetically separable nano CuFe2O4: an efficient and reusable heterogeneous catalyst for the green synthesis of thiiranes from epoxides with thiourea,” Journal of Sulfur Chemistry, 37, 537-545, 2016.
[42] R. Eisavi, F. Ahmadi, B. Ebadzade, S. Ghadernejad, “A green method for solvent-free conversion of epoxides to thiiranes using NH4SCN in the presence of NiFe2O4 and MgFe2O4 magnetic nanocatalysts,” Journal of Sulfur Chemistry, 38, 614-624, 2017.
[43] S. Hassanzadeh, R. Eisavi, M. Abbasian, “Preparation and characterization of magnetically separable MgFe2O4/Mg(OH)2 nanocomposite as an efficient heterogeneous catalyst for regioselective one‐pot synthesis of β‐chloroacetates from epoxides,” Applied Organometallic Chemistry, 32, e4520, 2018.
[44] R. Eisavi, S. Alifam, “ZnFe2O4 nanoparticles: a green and recyclable magnetic catalyst for fast and regioselective conversion of epoxides to vicinal hydroxythiocyanates using NH4SCN under solvent-free conditions,” Phosphorus, Sulfur, and Silicon and the Related Elements, 193, 211-217, 2017.
[45] S. Hassanzadeh, R. Eisavi, M. Abbasian, “Green synthesis of thiiranes from epoxides catalyzed by magnetically separable CuFe2O4/Mg(OH)2 nanocomposite in water under benign conditions,” Journal of Sulfur Chemistry, 40, 240-255, 2019.
[46] H. Iida, K. Takayannagi, T. Nakamishi, T. Osaka, “Synthesis of Fe3O4 nanoparticles with various sizes and magnetic properties by controlled hydrolysis,” Journal of Colloid and Interface Science, 314, 274-280, 2007.
[47] E. Mazario, P. Herrasti, M.P. Morales, N. Menendez, “Synthesis and characterization of CoFe2O4 ferrite nanoparticles obtained by an electrochemical method,” Nanotechnology, 23, 355708 (6pp), 2012.
[48] S. Sathiya, K. Parasuraman, M. Anbarasu, K. Balamurugan, “FT-IR, XRD, and SEM study of CoFe2O4 nanoparticles by chemical co-precipitation method,” NANO VISION, 5, 133-138, 2015.
[49] G. Fogassy, C. Pinel, G. Gelbard, “Solvent-free ring opening reaction of epoxides using quaternary ammonium salts as catalyst,” Catalysis Communications, 10, 557-560, 2009.