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Green Synthesis of Isoxazoline Derivatives Using Microwave Irradiation and Their Antifungal Activity
Asian Journal of Chemistry,
Vol. 28 No. 10 (2016): Vol 28 Issue 10
Abstract
Microwave irradiation method was used for synthesis of isoxazolines. Claisen Schmidt reaction of different aromatic aldehydes with acetanilide gave acrylamides (1a-1h) which on further reaction with hydroxylamine hydrochloride (in the presence of sodium hydroxide) afforded isoxazolines (2a-2h). Physical data of all the synthesized compounds were recorded. Isoxazolines were characterized by their IR and 1H NMR spectra. All the synthesized isoxazolines were screened for their antifungal activity against fungi namely Drechslera maydis and Rhizoctonia solani isolated from maize. Isoxazolines having chloro substitution on benzene ring found to be most effective followed by fluoro and nitro substituted compounds. None of the compound was registered as effective as Bavistin.
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- S. Bawa and H. Kumar, Indian J. Heterocycl. Chem., 14, 249 (2005).
- H.K. Hsieh, L.T. Tsao, J.P. Wang and C.N. Lin, J. Pharm. Pharmacol., 52, 163 (2000); doi:10.1211/0022357001773814.
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- R.F. Love and R.G. Duranlean, Preparation of 4-Nitroisoxazoles, US Patent 4172079 (1979).
- S. Pinto, C. Ozsancak, E. Tripoliti, S. Thobois, P. Limousin-Dowsey and P. Auzou, Lancet Neurol., 3, 547 (2004); doi:10.1016/S1474-4422(04)00854-3.
- S. Caddick, Tetrahedron, 51, 10403 (1995); doi:10.1016/0040-4020(95)00662-R.
- B.A. Fini and A. Breccia, Pure Appl. Chem., 71, 573 (1999); doi:10.1351/pac199971040573.
- M. Larhed and A. Hallberg, Drug Discov. Today, 6, 406 (2001); doi:10.1016/S1359-6446(01)01735-4.
- P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); doi:10.1016/S0040-4020(01)00906-1.
- L. Perreux and A. Loupy, Tetrahedron, 57, 9199 (2001); doi:10.1016/S0040-4020(01)00905-X.
- B.A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault and D. Mathe, Synthesis, 1213 (1998); doi:10.1055/s-1998-6083.
- R.S. Varma, Green Chem., 1, 43 (1999); doi:10.1039/a808223e.
- K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.
- A. Goyal, S. Sharma and J. Gaba, Indian J. Chem. (communicated).
- R.K. Grover and J.D. Moore, Phytopathology, 52, 876 (1962).
References
S. Bawa and H. Kumar, Indian J. Heterocycl. Chem., 14, 249 (2005).
H.K. Hsieh, L.T. Tsao, J.P. Wang and C.N. Lin, J. Pharm. Pharmacol., 52, 163 (2000); doi:10.1211/0022357001773814.
H. Kai, H. Matsumoto, N. Hattori, A. Takase, T. Fujiwara and H. Sugimoto, Bioorg. Med. Chem. Lett., 11, 1997 (2001); doi:10.1016/S0960-894X(01)00362-6.
S.H. Lee, G.S. Seo, J.Y. Kim, X.Y. Jin, H.D. Kim and D.H. Sohn, Eur. J. Pharmacol., 532, 178 (2006); doi:10.1016/j.ejphar.2006.01.005.
R.F. Love and R.G. Duranlean, Preparation of 4-Nitroisoxazoles, US Patent 4172079 (1979).
S. Pinto, C. Ozsancak, E. Tripoliti, S. Thobois, P. Limousin-Dowsey and P. Auzou, Lancet Neurol., 3, 547 (2004); doi:10.1016/S1474-4422(04)00854-3.
S. Caddick, Tetrahedron, 51, 10403 (1995); doi:10.1016/0040-4020(95)00662-R.
B.A. Fini and A. Breccia, Pure Appl. Chem., 71, 573 (1999); doi:10.1351/pac199971040573.
M. Larhed and A. Hallberg, Drug Discov. Today, 6, 406 (2001); doi:10.1016/S1359-6446(01)01735-4.
P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); doi:10.1016/S0040-4020(01)00906-1.
L. Perreux and A. Loupy, Tetrahedron, 57, 9199 (2001); doi:10.1016/S0040-4020(01)00905-X.
B.A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault and D. Mathe, Synthesis, 1213 (1998); doi:10.1055/s-1998-6083.
R.S. Varma, Green Chem., 1, 43 (1999); doi:10.1039/a808223e.
K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.
A. Goyal, S. Sharma and J. Gaba, Indian J. Chem. (communicated).
R.K. Grover and J.D. Moore, Phytopathology, 52, 876 (1962).