A convenient synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters by FeCl3/SiO2 nanoparticles as robust and efficient catalyst

Sima Kalhor Javad Safaei-Ghomi

Citation:  Sima Kalhor, Javad Safaei-Ghomi. A convenient synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters by FeCl3/SiO2 nanoparticles as robust and efficient catalyst[J]. Chinese Chemical Letters, 2015, 26(6): 735-738. doi: 10.1016/j.cclet.2015.01.035 shu

A convenient synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters by FeCl3/SiO2 nanoparticles as robust and efficient catalyst

    通讯作者: Javad Safaei-Ghomi,
摘要: A simple and green method has been developed for the synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters through a one-pot three-component condensation reaction of primary amines, ethyl acetoacetate and chalcones using FeCl3/SiO2 nanoparticles in ethanol. This method has several advantages such as high to excellent product yields in short time, using an inexpensive and reusable catalyst and available starting material.

English

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    1. [1] K.L. Kozielski, S.Y. Tzeng, J.J. Green, A bioreducible linear poly(β-amino ester) for siRNA delivery, Chem. Comm. 49 (2013) 5319-5321.[1] K.L. Kozielski, S.Y. Tzeng, J.J. Green, A bioreducible linear poly(β-amino ester) for siRNA delivery, Chem. Comm. 49 (2013) 5319-5321.

    2. [2] G.T. Zugates, N.C. Tedford, A. Zumbuehl, et al., Gene delivery properties of endmodified poly(β-amino ester)s, Bioconj. Chem. 18 (2007) 1887-1896.[2] G.T. Zugates, N.C. Tedford, A. Zumbuehl, et al., Gene delivery properties of endmodified poly(β-amino ester)s, Bioconj. Chem. 18 (2007) 1887-1896.

    3. [3] K.R. Guertin, C.J. Gardner, S.I. Klein, et al., Optimization of the β-aminoester class of factor Xa inhibitors. Part 2: identification of FXV673 as a potent and selective inhibitor with excellent in vivo anticoagulant activity, Bioorg. Med. Chem. Lett. 12 (2002) 1671-1674.[3] K.R. Guertin, C.J. Gardner, S.I. Klein, et al., Optimization of the β-aminoester class of factor Xa inhibitors. Part 2: identification of FXV673 as a potent and selective inhibitor with excellent in vivo anticoagulant activity, Bioorg. Med. Chem. Lett. 12 (2002) 1671-1674.

    4. [4] J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, et al., SnCl2/nano SiO2: a green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4Hpyrans, Chin. Chem. Lett. 24 (2013) 921-925.[4] J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, et al., SnCl2/nano SiO2: a green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4Hpyrans, Chin. Chem. Lett. 24 (2013) 921-925.

    5. [5] J.P. Wan, Y. Liu, Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines, RSC Adv. 2 (2012) 9763-9777.[5] J.P. Wan, Y. Liu, Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines, RSC Adv. 2 (2012) 9763-9777.

    6. [6] B. Jiang, T. Rajale, W. Wever, et al., Multicomponent reactions for the synthesis of heterocycles, Chem. Asian J. 5 (2010) 2318-2335.[6] B. Jiang, T. Rajale, W. Wever, et al., Multicomponent reactions for the synthesis of heterocycles, Chem. Asian J. 5 (2010) 2318-2335.

    7. [7] F. Yu, R. Huang, H. Ni, et al., Three-component stereoselective synthesis of spirooxindole derivatives, Green Chem. 15 (2013) 453-462.[7] F. Yu, R. Huang, H. Ni, et al., Three-component stereoselective synthesis of spirooxindole derivatives, Green Chem. 15 (2013) 453-462.

    8. [8] A. Bhunia, T. Kaicharla, D. Porwal, et al., Multicomponent reactions involving phosphines, arynes and aldehydes, Chem. Commun. 50 (2014) 11389-11392.[8] A. Bhunia, T. Kaicharla, D. Porwal, et al., Multicomponent reactions involving phosphines, arynes and aldehydes, Chem. Commun. 50 (2014) 11389-11392.

    9. [9] J. Safaei-Ghomi, H. Shahbazi-Alavi, E. Heidari-Baghbahadorani, SnO nanoparticles as an efficient catalyst for the one-pot synthesis of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines, RSC Adv. 4 (2014) 50668-50677.[9] J. Safaei-Ghomi, H. Shahbazi-Alavi, E. Heidari-Baghbahadorani, SnO nanoparticles as an efficient catalyst for the one-pot synthesis of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines, RSC Adv. 4 (2014) 50668-50677.

    10. [10] X.H. Zhanga, J.F. Yanb, L. Fana, et al., Synthesis and antidiabetic activity of β-acetamido ketones, Acta Pharm. Sin. B 2 (2011) 100-105.[10] X.H. Zhanga, J.F. Yanb, L. Fana, et al., Synthesis and antidiabetic activity of β-acetamido ketones, Acta Pharm. Sin. B 2 (2011) 100-105.

    11. [11] V.M. Joshi, R.L. Magar, P.B. Throat, et al., Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst, Chin. Chem. Lett. 25 (2014) 455-458.[11] V.M. Joshi, R.L. Magar, P.B. Throat, et al., Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst, Chin. Chem. Lett. 25 (2014) 455-458.

    12. [12] M. Kassaee, R. Mohammadi, H. Masrouri, F. Movahedi, Nano TiO2 as a heterogeneous catalyst in an efficient one-pot three-component Mannich synthesis of β-aminocarbonyls, Chin. Chem. Lett. 22 (2011) 1203-1206.[12] M. Kassaee, R. Mohammadi, H. Masrouri, F. Movahedi, Nano TiO2 as a heterogeneous catalyst in an efficient one-pot three-component Mannich synthesis of β-aminocarbonyls, Chin. Chem. Lett. 22 (2011) 1203-1206.

    13. [13] F. Alonso, Y. Moglie, G. Radivoy, et al., Multicomponent click synthesis of 1,2,3-triazoles from epoxides in water catalyzed by copper nanoparticles on activated carbon, J. Org. Chem. 76 (2011) 8394-8405.[13] F. Alonso, Y. Moglie, G. Radivoy, et al., Multicomponent click synthesis of 1,2,3-triazoles from epoxides in water catalyzed by copper nanoparticles on activated carbon, J. Org. Chem. 76 (2011) 8394-8405.

    14. [14] N. Koukabi, E. Kolvari, A. Khazaei, et al., Hantzsch reaction on free nano-Fe2O3-catalyst: excellent reactivity combined with facile catalyst recovery and recyclability, Chem. Commun. 47 (2011) 9230-9232.[14] N. Koukabi, E. Kolvari, A. Khazaei, et al., Hantzsch reaction on free nano-Fe2O3-catalyst: excellent reactivity combined with facile catalyst recovery and recyclability, Chem. Commun. 47 (2011) 9230-9232.

    15. [15] K. Chanda, S. Rej, M.H. Huang, Facet-dependent catalytic activity of Cu2O nanocrystals in the one-pot synthesis of 1,2,3-triazoles by multicomponent click reactions, Chem. Eur. J. 19 (2013) 16036-16043.[15] K. Chanda, S. Rej, M.H. Huang, Facet-dependent catalytic activity of Cu2O nanocrystals in the one-pot synthesis of 1,2,3-triazoles by multicomponent click reactions, Chem. Eur. J. 19 (2013) 16036-16043.

    16. [16] M.B. Gawande, A. Velhinho, I.D. Nogueira, et al., A facile synthesis of cysteine-ferrite magnetic nanoparticles for application in multicomponent reactions -a sustainable protocol, RSC Adv. 2 (2012) 6144-6149.[16] M.B. Gawande, A. Velhinho, I.D. Nogueira, et al., A facile synthesis of cysteine-ferrite magnetic nanoparticles for application in multicomponent reactions -a sustainable protocol, RSC Adv. 2 (2012) 6144-6149.

    17. [17] L. Abahmane, J.M. Köhler, G.A. Groß, Gold-nanoparticle-catalyzed synthesis of propargylamines: the traditional A3-multicomponent reaction performed as a two-step flow process, Chem. Eur. J. 17 (2011) 3005-3010.[17] L. Abahmane, J.M. Köhler, G.A. Groß, Gold-nanoparticle-catalyzed synthesis of propargylamines: the traditional A3-multicomponent reaction performed as a two-step flow process, Chem. Eur. J. 17 (2011) 3005-3010.

    18. [18] C.W. Lim, I.S. Lee, Magnetically recyclable nanocatalyst systems for the organic reactions, Nano Today 5 (2010) 412-434.[18] C.W. Lim, I.S. Lee, Magnetically recyclable nanocatalyst systems for the organic reactions, Nano Today 5 (2010) 412-434.

    19. [19] A.R. Kiasat, J. Davarpanah, Fe3O4@silica sulfuric acid nanoparticles: an efficient reusable nanomagnetic catalyst as potent solid acid for one-pot solvent-free synthesis of indazolo[21-b]phthalazine-triones and pyrazolo[1,2-b]phthalazinediones, J. Mol. Catal. A: Chem. 373 (2013) 46-54.[19] A.R. Kiasat, J. Davarpanah, Fe3O4@silica sulfuric acid nanoparticles: an efficient reusable nanomagnetic catalyst as potent solid acid for one-pot solvent-free synthesis of indazolo[21-b]phthalazine-triones and pyrazolo[1,2-b]phthalazinediones, J. Mol. Catal. A: Chem. 373 (2013) 46-54.

    20. [20] A. Mobinikhaledi, H. Moghanian, S. Pakdel, Microwave-assisted efficient synthesis of azlactone derivatives using 2-aminopyridine-functionalized sphere SiO2 nanoparticles as a reusable heterogeneous catalyst, Chin. Chem. Lett. 26 (2015) 557-563.[20] A. Mobinikhaledi, H. Moghanian, S. Pakdel, Microwave-assisted efficient synthesis of azlactone derivatives using 2-aminopyridine-functionalized sphere SiO2 nanoparticles as a reusable heterogeneous catalyst, Chin. Chem. Lett. 26 (2015) 557-563.

    21. [21] Y.G. Sun, T.T. Truong, Y.Z. Liu, Y.X. Hu, Encapsulation of superparamagnetic Fe3O4@SiO2 core/shell nanoparticles in MnO2 microflowers with high surface areas, Chin. Chem. Lett. 26 (2015) 233-237.[21] Y.G. Sun, T.T. Truong, Y.Z. Liu, Y.X. Hu, Encapsulation of superparamagnetic Fe3O4@SiO2 core/shell nanoparticles in MnO2 microflowers with high surface areas, Chin. Chem. Lett. 26 (2015) 233-237.

    22. [22] J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, SnCl2/nano SiO2: a green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4Hpyrans, Chin. Chem. Lett. 24 (2013) 921-925.[22] J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, SnCl2/nano SiO2: a green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4Hpyrans, Chin. Chem. Lett. 24 (2013) 921-925.

    23. [23] J. Safaei-Ghomi, A. Ziarati, S. Zahedi, Silica (NPs) supported Fe (III) as a reusable heterogeneous catalyst for the one-pot synthesis of 1, 4-dihydropyridines under mild conditions, J. Chem. Sci. 124 (2012) 933-939.[23] J. Safaei-Ghomi, A. Ziarati, S. Zahedi, Silica (NPs) supported Fe (III) as a reusable heterogeneous catalyst for the one-pot synthesis of 1, 4-dihydropyridines under mild conditions, J. Chem. Sci. 124 (2012) 933-939.

    24. [24] J. Safaei-Ghomi, M.A. Ghasemzadeh, S. Zahedi, FeCl3 nano SiO2: an efficient heterogeneous nano catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]-xanthenes and 1,8-dioxo-octahydro-xanthenes under solvent-free conditions, S. Afr. J. Chem. 65 (2012) 191-195.[24] J. Safaei-Ghomi, M.A. Ghasemzadeh, S. Zahedi, FeCl3 nano SiO2: an efficient heterogeneous nano catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]-xanthenes and 1,8-dioxo-octahydro-xanthenes under solvent-free conditions, S. Afr. J. Chem. 65 (2012) 191-195.

    25. [25] J. Safaei-Ghomi, S. Zahedi, M.A. Ghasemzadeh, Nano silica supported ferric chloride as a green and efficient catalyst for one pot synthesis of 12-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-ones, Iran J. Catal. 2 (2012) 27-30.[25] J. Safaei-Ghomi, S. Zahedi, M.A. Ghasemzadeh, Nano silica supported ferric chloride as a green and efficient catalyst for one pot synthesis of 12-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-ones, Iran J. Catal. 2 (2012) 27-30.

    26. [26] V. Sridharan, J.C. Menendez, Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction, Org. Lett. 10 (2008) 4303-4306.[26] V. Sridharan, J.C. Menendez, Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction, Org. Lett. 10 (2008) 4303-4306.

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  • 发布日期:  2015-02-07
  • 收稿日期:  2014-12-08
  • 网络出版日期:  2015-01-13
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