Abstract
In this work, it was found that magnesium oxide nanoparticles (nano-MgO) catalyzed one-pot three-component reaction of hydroxylamine hydrochloride with aryl aldehydes (or heteroaryl aldehydes) and β-oxoesters to synthesize some biologically active isoxazole-5(4H)-one-based heterocycles. The reactions were completed using 3 mol% catalyst loading in aqueous medium at room temperature. Nano-MgO was synthesized by precipitation and hydrothermal treatment of aqueous salt solution. The structure of the nano-MgO was characterized by X-ray diffraction (XRD) and scanning electron microscopy (SEM) analyses. The presented environmentally friendly heterocyclization offers some interesting merits, including safety, high product yield, mild conditions, low cost, minimal waste, good atom efficiency, catalyst recoverable, energy efficiency, avoidance of hazardous organic solvents, and easy workup.
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W.T. Meng, Y. Zheng, J. Nie, H.Y. Xiong, J.A. Ma, J. Org. Chem. 78, 559 (2013)
H. Zhang, B. Wang, L. Cui, X. Bao, J. Qu, Y. Song, Eur. J. Org. Chem. 2143 (2015)
G.Q. Li, Y.B. Zhang, H.S. Guan, Fitoterapia 79, 238 (2008)
T.F. Niu, M.F. Lv, L. Wang, W.B. Yi, C. Cai, Org. Biomol. Chem. 11, 1040 (2013)
A.P. Kozikowski, S. Tapadar, D.N. Luchini, K.H. Kim, D.D. Billadeau, J. Med. Chem. 51, 4370 (2008)
A.A. Vieira, F.R. Bryk, G. Conte, A.J. Bortoluzzi, H. Gallardo, Tetrahedron Lett. 50, 905 (2009)
J. Yong, C. Lu, X. Wu, Med. Chem. Commun. 5, 968 (2014)
S.K. Laughlin, M.P. Clark, J.F. Djung, A. Golebiowski, T.A. Brugel, M. Sabat, R.G. Bookland, M.J. Laufersweiler, J.C. VanRens, J.A. Townes, B. De, L.C. Hsieh, S.C. Xu, R.L. Walter, M.J. Mekel, M.J. Janusz, Bioorg. Med. Chem. Lett. 15, 2399 (2005)
A.H. Reshak, S. Azam, Mater. Sci. Semicond. Process. 30, 197 (2015)
S. Biju, M.L.P. Reddy, A.H. Cowley, K.V. Vasudevan, J. Mater. Chem. 19, 5179 (2009)
E.S. Darwish, K.A. Atia, A.M. Farag, Heterocycles 89, 1393 (2014)
A.M. Jawalekar, E. Reubsaet, F.P.J.T. Rutjes, F.L. van Delft, Chem. Commun. 47, 3198 (2011)
H.L. Liu, Z.F. Geng, S.Y. Zhang, J. Han, Heterocycles 89, 1221 (2014)
W.S. Hamama, M.E. Ibrahim, H.H. Zoorob, Synth. Commun. 43, 2393 (2013)
W. Hallenbach, O. Guth, T. Seitz, H.J. Wroblowsky, P. Desbordes, U. Wachendorff-Neumann, P. Dahmen, A. Voerste, P. Lösel, O. Malsam, R. Rama, H. Hadano, 2012, US Patent, Pub. No.: US 2012/0065063A1
W. Hallenbach, O. Guth, T. Seitz,, H.J. Wroblowsy, P. Desbords, U. Wachendorff, P. Dahmen, A. Voerste, P. Losel, O. Malsam, R. Rama, H. Hadano, 2011, WIPO Patent Application WO/2011/161035A1
J.P. Demers, W.E. Hageman, S.G. Johnson, D.H. Klaubert, R.A. Look, J.B. Moore, Bioorg. Med. Chem. Lett. 4, 2451 (1994)
T. Ishioka, A. Tanatani, K. Nagasawa, Y. Hashimoto, Bioorg. Med. Chem. Lett. 13, 2655 (2003)
T. Ishioka, A. Kubo, Y. Koiso, K. Nagasawa, A. Itai, Y. Hashimoto, Bioorg. Med. Chem. 10, 1555 (2002)
B. Kafle, N.G. Aher, D. Khadka, H. Park, H. Cho, Chem. Asian J. 6, 2073 (2011)
N. Panathur, N. Gokhale, U. Dalimba, P.V. Koushik, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 25, 2768 (2015)
X.H. Zhang, L.Y. Wang, Y.H. Zhan, Y.L. Fu, G.H. Zhai, Z.Y. Wen, J. Mol. Struct. 994, 371 (2011)
X.H. Zhang, Y.H. Zhan, D. Chen, D. Chen, F. Wang, L.Y. Wang, Dyes Pigments 93, 1408 (2012)
F. Wang, A.W. Harper, M.S. Lee, L.R. Dalton, Chem. Mater. 11, 2285 (1999)
S. Alıas, R. Andreu, M.J. Blesa, M.A. Cerdan, S. Franco, J. Garın, C. Lopez, J. Orduna, J. Sanz, R. Alicante, B. Villacampa, M. Allain, J. Org. Chem. 73, 5890 (2008)
D. Jiang, Z. Xue, Y. Li, H. Liu, W. Yang, J. Mater. Chem. 1, 5694 (2013)
P.V. Bedworth, Y. Cai, A. Jen, S.R. Marder, J. Org. Chem. 61, 2242 (1996)
S. Biju, M.L.P. Reddy, R.O. Freire, Inorg. Chem. Commun. 10, 393 (2007)
E. Aret, H. Meekes, E. Vlieg, G. Deroover, Dyes Pigments 72, 339 (2007)
M.R.N. Capreti, I.D. Jurberg, Org. Lett. 17, 2490 (2015)
J.S. Wzorek, T.F. Knopfel, I. Sapountzis, D.A. Evans, Org. Lett. 14, 5840 (2012)
C.O. Kappe, D. Kvaskoff, D.W.J. Moloney, R. Flammang, C. Wentrup, J. Org. Chem. 66, 1827 (2001)
T.M. Kaiser, J.H. Huang, J. Yang, J. Org. Chem. 78, 6297 (2013)
I. Dias-Jurberg, F. Gagosz, S.Z. Zard, Org. Lett. 12, 416 (2010)
G. Sabitha, M.M. Reddy, B. Archana, J.S. Yadav, Synth. Commun. 28, 573 (1998)
B.D. Cui, S.W. Li, J. Zuo, Z.J. Wu, X.M. Zhang, W.C. Yuan, Tetrahedron 70, 1895 (2014)
C. Wentrup, M. Wiedenstritt, H.W. Winter, Aust. J. Chem. 68, 1233 (2015)
C. Wentrup, H.W. Winter, Angew. Chem. Int. Ed. Engl. 17, 609 (1978)
C. Wentrup, J. Becker, H.W. Winter, Angew. Chem. Int. Ed. 54, 5702 (2015)
G.I. Yranzo, J. Elguero, R. Flammang, C. Wentrup, Eur. J. Org. Chem. 2001, 2209 (2001)
I. Nakamura, M. Okamoto, M. Terada, Org. Lett. 12, 2453 (2010)
M. Cocivera, A. Emo, H.E. Chen, S. Vaish, J. Am. Chem. Soc. 98, 7362 (1976)
D. Villemin, B. Martin, B. Garrigues, Synth. Commun. 23, 2251 (1993)
G. Brancatelli, G. Bruno, F. Nicolo, M. Cordaro, G. Grassi, F. Risitano, A. Scala, J. Mol. Struct. 998, 157 (2011)
J.J. Donleawy, E.E. Gilbert, J. Am. Chem. Soc. 59, 1072 (1937)
D.B. Lowe, S. Magnuson, N. Qi, A.M. Campbell, J. Cook, Z. Hong, M. Wang, M. Rodriguez, F. Achebe, H. Kluender, W.C. Wong, W.H. Bullock, A.I. Salhanick, T. Witman-Jones, M.E. Bowling, C. Keiper, K.B. Clairmont, Bioorg. Med. Chem. Lett. 14, 3155 (2004)
A.P. Chavan, A.B. Pinjari, P.C. Mhaske, J. Heterocycl. Chem. 52, 1911 (2015)
Q. Liu, R.T. Wu, J. Chem. Res. 35, 598 (2011)
Q. Liu, Y.N. Zhang, Bull. Korean Chem. Soc. 32, 3559 (2011)
Y.Q. Zhang, J.J. Ma, C. Wang, J.C. Li, D.N. Zhang, X.H. Zang, J. Li, Chin. J. Org. Chem. 28, 141 (2008)
K. Ablajan, H. Xiamuxi, Chin. Chem. Lett. 22, 151 (2011)
M. Mirzazadeh, G.H. Mahdavinia, Eur. J. Chem. 9, 425 (2012)
S.N. Maddila, S. Maddila, W.E. Zyl, S.B. Jonnalagadda, Res. Chem. Intermed. (2015). doi:10.1007/s11164-015-2167-2
H. Kiyani, F. Ghorbani, Heterocycl. Lett. 3, 359 (2013)
H. Kiyani, F. Ghorbani, Elixir Org. Chem. 58, 14948 (2013)
H. Kiyani, F. Ghorbani, Org. Chem. Indian J. 13, 97 (2013)
H. Kiyani, F. Ghorbani, Open J. Org. Chem. 1, 5 (2013)
Q. Liu, X. Hou, Phosphorus Sulfur Silicon Relat. Elem. 187, 448 (2012)
M.G. Dekamin, S.Z. Peyman, Monatsh. Chem. (2015). doi:10.1007/s00706-015-1565-x
H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 2653 (2015)
H. Kiyani, F. Ghorbani, Heterocycl. Lett. 3, 145 (2013)
H. Kiyani, F. Ghorbani, J. Saudi Chem. Soc. (2013). doi:10.1016/j.jscs.2013.11.002
H. Kiyani, M. Jabbari, A. Mosallanezhad, Jordan J. Chem. 9, 279 (2014)
H. Kiyani, A. Kanaani, D. Ajloo, F. Ghorbani, M. Vakili, Res. Chem. Intermed. 41, 7739 (2015)
H. Kiyani, H. Darbandi, A. Mosallanezhad, F. Ghorbani, Res. Chem. Intermed. 41, 7561 (2015)
H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 7847 (2015)
D. Setamdideh, J. Mex. Chem. Soc. 59, 191 (2015)
A.U. Khandebharad, S.R. Sarda, C.H. Gill, B.R. Agrawal, Res. J. Chem. Sci. 5, 27 (2015)
F. Saikh, J. Das, S. Ghosh, Tetrahedron Lett. 54, 4679 (2013)
Y.Q. Zhang, C. Wang, M.Y. Zhang, P.L. Cui, Y.M. Li, X. Zhou, J.C. Li, Chin. J. Org. Chem. 28, 914 (2008)
K. Ablajan, H. Xiamuxi, Synth. Commun. 42, 1128 (2012)
Q.F. Cheng, X.Y. Liu, Q.F. Wang, L.S. Liu, W.J. Liu, Q. Lin, X.J. Yang, Chin. J. Org. Chem. 29, 1267 (2009)
S. Tu, J. Zhang, R. Jia, B. Jiang, Y. Zhang, H. Jiang, Org. Biomol. Chem. 5, 1450 (2007)
B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, B.J. Sreedhar, J. Am. Chem. Soc. 127, 13167 (2005)
V.R. Chintareddy, M.L. Kantam, Catal. Surv. Asia 15, 89 (2011)
B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004 (2012)
G. Brahmachari, S. Laskar, Phosphorus Sulfur Silicon Relat. Elem. 189, 873 (2014)
C. Xu, J.K. Bartley, D.I. Enache, D.W. Knight, G.J. Hutchings, Synthesis 3468 (2005)
M. Abaszadeh, M. Seifi, A. Asadipour, Synth. React. Inorg. Met. Org. Chem. 46, 512 (2016)
H. Sheibani, M. Seifi, A. Bazgir, Synth. Commun. 39, 1055 (2009)
L. Chakrapani, M.L. Kantam, Synth. Commun. 41, 3442 (2011)
V.K. Das, A.J. Thakur, Tetraderon Lett. 54, 4164 (2013)
J. Safaei-Ghomi, F. Eshteghal, M.A. Ghasemzadeh, Acta Chim. Slov. 61, 703 (2014)
M. Tajbakhsh, M. Farhang, A.S. Hosseini, J. Iran. Chem. Soc. 11, 665 (2014)
N. Shariati, R.J. Baharfar, Chin. Chem. Soc. 61, 337 (2014)
H. Naeimi, K. Rabiei, M. Rezaei, F. Meshkani, J. Iran. Chem. Soc. 10, 161 (2013)
H. Naeimi, N. Alishahi, J. Exp. Nanosci. 10, 222 (2015)
H. Mirzaie, A. Davoodnia, Chin. J. Catal. 33, 1502 (2012)
Z. Zarnegar, J. Safari, J. Exp. Nanosci. 10, 651 (2015)
V.K. Das, R.R. Devi, A. Thakur, J. Appl. Catal. A Gen. 456, 118 (2013)
J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci. 7, 17 (2013)
H. Naeimi, Z. Rashid, A.H. Zarnani, R. Ghahremanzadeh, J. Nanopart. Res. 16, 2416 (2014)
F. Shirini, M. Abedini, J. Nanosci. Nanotechnol. 13, 4838 (2013)
D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron 63, 3093 (2007)
S.H.S. Azzam, G.T. Chandrappa, M.A. Pasha, Lett. Org. Chem. 10, 283 (2013)
A. Mossafaii Rad, M. Mokhtary, Int. Nano Lett. 5, 109 (2015)
M. Hosseini-Sarvari, G. Parhizgar, Green Chem. Lett. Rev. 5, 439 (2012)
R. Baharfar, N. Shariati, C. R. Chimie 17, 413 (2014)
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Kiyani, H., Ghorbani, F. Expeditious green synthesis of 3,4-disubstituted isoxazole-5(4H)-ones catalyzed by nano-MgO. Res Chem Intermed 42, 6831–6844 (2016). https://doi.org/10.1007/s11164-016-2498-7
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DOI: https://doi.org/10.1007/s11164-016-2498-7