DOWEX(R)50WX4/H2O: A Green System for a One-pot and Three-Component Synthesis of isoxazol-5(4H)-one Derivatives

Authors

  • Davood Setamdideh Islamic Azad University

DOI:

https://doi.org/10.29356/jmcs.v59i3.34

Keywords:

DOWEX(R)50WX4, isoxazol-5(4H)-one, one-pot reaction, water, green chemistry

Abstract

A one-pot and three-component synthesis of 3-methyl-4-arylmethyleneisoxazol-5(4H)-ones was developed in the presence of DOWEX(R)50WX4 as the catalyst. The products were obtained in high yields (93-96%) and short reaction times (30-60 min). The present method provides an easy and efficient approach for the synthesis of this class of compounds, because of its clean reaction profile and operational simplicity.

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Author Biography

Davood Setamdideh, Islamic Azad University

Department of Chemistry, Mahabad Branch, Islamic Azad University

References

a) Knecht, W.; Löffler, M. Biochem. Pharmacol. 1998, 56, 1259-1264. b) Suryawanshi, S. N.; Tiwari, A.; Chandra, N.; Ramesh.; Gupta, S. Bioorg. Med. Chem. Lett. 2012, 22, 6559-6562. c) Kafle, B.; Cho, H. Bull. Korean Chem. Soc. 2012, 33, 275-277. d) Changtam, C.; Hongmanee, P.; Suksamrarn, A. Eur. J. Med. Chem. 2010, 45, 4446-4457. e) Santos, M. M. M.; Faria, N.; Iley, J.; Coles, S. J.; Hursthouse, M. B.; Martins, M. L.; Moreira, R. Bioorg. Med. Chem. Lett. 2010, 20, 193-195. f) Conti, P.; Tamborini, L.; Pinto, A.; Sola, L.; Ettari, R.; Mercurio, C.; De Micheli, C. Eur. J. Med. Chem. 2010, 45, 4331-4338. g) Kano, H.; Adachi, I.; Kido, R.; Hirose, K. J. Med. Chem. 1967, 10, 411-418. h) Giovannoni, M. P.; Vergelli, C.; Ghelardini, C.; Galeotti, N.; Bartolini, A.; Piaz, V. D. J. Med. Chem. 2003, 46, 1055-1059. i) Srinivas, A.; Nagaraj, A.; Reddy, C. S. Eur. J. Med. Chem. 2010, 45, 2353-2358. j) Padmaja, A.; Rajasekhar, C.; Muralikrishna, A.; Padmavathi, V. Eur. J. Med. Chem. 2011, 46, 5034-5038. k) Padmaja, A.; Payani, T.; Reddy, G. D.; Padmavathi, V. Eur. J. Med. Chem. 2009, 44, 4557-4566. l) Prashanthi, Y.; Kiranmai, K.; Subhashini, N. J. P.; Shivaraj. Spectrochim. Acta A. 2008, 70, 30-35. m) Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; Seibert, K. J. Med. Chem. 2000, 43, 775-777. n) Karabasanagouda, T.; Adhikari, A. V.; Girisha, M. Indian J. Chem. B 2009, 48, 430-437. o) Kamal, A.; Bharathi, E. V.; Reddy, J. S.; Janaki, M.; Ramaiah, D.; Reddy, M. K.; Viswanath, A.; Reddy, T. L.; Shaik, T. B.; Pushpavalli, S. N.; Bhadra, M. P. Eur. J. Med. Chem. 2011, 46, 691-703. p) Lee, Y. S.; Park, S. M.; Kim, B. H. Bioorg. Med. Chem. Lett. 2009, 19, 1126-1128. q) Mao, J.; Yuan, H.; Wang, Y.; Wan, B.; Pak, D.; He, R.; Franzblau, S. G. Bioorg. Med. Chem. Lett. 2010, 20, 1263-1268. r) Tavares, A.; Arruda, B. C.; Boes, E. L.; Stefani, V.; Stassen, H. K.; Campo, L. F.; Bechtoldb, I. H.; Merlo, A. A. J. Braz. Chem. Soc. 2012, 23, 880-888. s) Zhang, X. H.; Wang, L. Y.; Zhan, Y. H.; Fu, Y. L.; Zhaia, G. H.; Wenc, Z. Y. J. Mol. Struct. 2011, 994, 371-378. t) Zhang, X. H.; Zhan, Y. H.; Chen, D.; Wang, F.; Wang, L. Y. Dyes Pigments 2012, 93, 1408-1415. u) Pu, S.; Li, H.; Liu, G.; Liu, W.; Cui, S.; Fan, C. Tetrahedron 2011, 67, 1438-1447. v) Liu, G.; Liu, M.; Pu, S.; Fan, C.; Cui, S. Tetrahedron 2012, 68, 2267-2275.

a) Zhang, Y. Q.; Ma, J. J.; Wang, C.; Li, J. C.; Zhang, D. N.; Zang, X. H.; Li, J. Chin. J. Org Chem. 2008, 28, 141-144. b) Liu, Q.; Wu, R. T. J. Chem. Res. 2011, 10, 598-599. c) Liu, Q.; Zhang, Y. N. Bull. Korean Chem. Soc. 2011, 32, 3559-3560. d) Kiyani, H.; Ghorbani, F. Elixir Org. Chem. 2013, 58A, 14948-14950. e) Kiyani, H.; Ghorbani, F. Heterocycl Lett. 2013, 3, 359-369. f) Kiyani, H.; Ghorbani, F. Heterocycl Lett. 2013, 3, 145-153. g) Liu, Q.; Hou, X. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 448-453. h) Kiyani, H. Org. Chem. Indian J. 2013, 9, 97-101. i) Kiyani, H.; Ghorbani, F. Open J. Org. Chem. 2013, 1, 5-9. j) Zhang, Y. Q.; Wang, C.; Zhang, M. Y.; Cui, P. L.; Li, Y. M.; Zhou, X.; Li, J. C. Chin. J. Org. Chem. 2008, 28, 914-917. k) Cheng, Q. F.; Liu, X. Y.; Wang, Q. F.; Liu, L. S.; Liu, W. J.; Lin, Q.; Yang, X. J. Chin. J. Org. Chem. 2009, 29, 1267-1271. l) Saikh, F.; Das, J.; Ghosh, S. Tetrahedron Lett. 2013, 54, 4679-4682. m) Fozooni, S.; Gholam Hosseinzadeh, N.; Hamidian, H.; Akhgar, M. R. J. Braz. Chem. Soc. 2013, 24, 1649-1655. n) Chavan, A. P.; Pinjari, A. B.; Mhaske, P. C. 2014, J. Heterocyclic Chem. doi: 10.1002/jhet.2293.

a) Singh, M. S.; Chowdhry, S. RSC Adv. 2012, 2, 4547-4592. b) Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Helv. Chem. Acta 2009, 92, 2118-2124. c) Jiang, B.; Wang, X.; Shi, F.; Tu, S. J.; Li, G. Org. Biomol. Chem. 2011, 9, 4025-4028. d) Wan, J. P.; Liu, Y. RSC Adv. 2012, 2, 9763-9777. e) D?mling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083-3135. f) Ram?n, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602-1634. g) de Graaff, C.; Ruijter, E.; Orru, R. V. A. Chem. Soc. Rev. 2012, 41, 3969-4009. h) Ugi, I. Pure Appl. Chem. 2001, 73, 187-191. i) Kumaravel, K.; Vasuki, G. Curr. Org. Chem. 2009, 13, 1820-1841. j) Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725-748. k) Gu, Y. Green Chem. 2012, 14, 2091-2128. l) Siamala, M. Org. Prep. Proced. Int. 2009, 41, 1-68.

a) Setamdideh, D.; Khezri, B.; Esmaeilzadeh, S. J. Chin. Chem. Soc. 2012, 59, 1119-1124. b) Setamdideh, D.; Khezri, B.; Alipouramjad, A. J. Chin. Chem. Soc. 2013, 60, 590-596. c) Sofighaderi, S.; Setamdideh, D. Orient. J. Chem. 2013, 29, 1135-1137. d) Setamdideh, D.; Sepehraddin, F. J. Mex. Chem. Soc. 2014, 58, 22-26. e) Azizi Asl, P.; Setamdideh, D. J. Chin. Chem. Soc. 2014, 59, 940-944. f) Setamdideh, D. J. Mex. Chem. Soc. 2014, 58, 230-234.

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Published

2017-10-12

Issue

Vol. 59 No. 3 (2015): Regular Issue

Section

Regular Articles

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