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An Efficient Method for the Synthesis of Isoxazolines Under Microwave Irradiation and Solvent-Free Conditions
Corresponding Author(s) : Pravin O. Patil
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
A facile method for the synthesis of new isoxazoline derivatives are being reported starting from substituted 1-(1H-indol-3-yl)-3-(substituted aryl)-prop-1-en-3-ones and hydroxylamine hydrochloride under solvent free conditions and microwave irradiation. This approach has advantages such as short reaction time, moderate to excellent yield, over the conventional synthesis. The structures of the compounds were confirmed by 1H NMR, IR, mass spectra and elemental (C, H, N) analysis.
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- R. Preeti, V.K. Srivastava and K. Ashok, Eur. J. Med. Chem., 39, 449 (2004).
- N. Siddiqui and M.S.A. Ahsan, Acta Pharm., 58, 445 (2008).
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- C. Mengchao, O. Masahiro, K. Hiroyuki, L.L. Bo and S. Hideo, Bioorg. Med. Chem. Lett., 21, 980 (2011).
- S.S. Panda and P.V.R. Chaudhari, Indian J. Pharm. Sci., 70, 208 (2008).
- U. Misra, A. Hitkari, A.K. Saxena, S. Gurtu and S. Shanker, Eur. J. Med. Chem., 31, 629 (1996).
- S.Y. Hae, J.L. Eun, E.L. Jie, K.P. Woo, J.B. Du, S.C. Yong, Y.K. Hun, C. Hyunah and N.P. Ae, Bull. Korean. Chem. Soc., 30, 1873 (2009).
- A. Padmaja, T. Payani, G.D. Reddy and V. Padmavathi, Eur. J. Med. Chem., 44, 4557 (2009).
- T. Karthikeyan, V. Seelan, K.G. Lalitha and P.T. Perumal, Bioorg. Med. Chem. Lett., 19, 3370 (2009).
- K.J. Ahmed, S. Reddy, M.J. Ramaiah, D.E. Dastagiri, V.M. Bharathi, A.F. Ameruddin, S.N.C.V.L. Pushpavalli, M. Pal-Bhadra, A. Juvekar, S. Sen and S. Zingde, Eur. J. Med. Chem., 45, 3924 (2010).
- Y.R. Prasad, P.R. Kumar and B. Ramesh, Int. J. Chem. Sci., 5, 542 (2007).
- S. Balachandran, P.K. Gadekar, S. Parkale, V.N. Yadav, D. Kamath, S. Ramaswamy, S. Sharma, R.A. Vishwakarma and N.M. Dagia, Bioorg. Med. Chem. Lett., 21, 1508 (2011).
- G. Ahmad, P. Mishra, K. Mishra, P. Gupta, P.P. Yadav, P. Tiwari, A.K. Tamarkar, A.K. Srivastava and R. Maurya, Bioorg. Med. Chem. Lett., 15, 2139 (2006).
- A.A.R. Mohamed and M.H.A. Eman, Monatsh. Chem., 140, 229 (2009).
- T. Shah and V. Desai, J. Serb. Chem. Soc., 72, 443 (2007).
- S.B. Lohiya and B.J. Ghiya, Indian J. Chem., 25B, 279 (1996).
- S.R. Mohane, V.G. Thakare and B.N. Berad, Asian J. Chem., 21, 7422 (2009).
- V. Tiwari, P. Ali and J. Meshram, Ultrasonics Sonochem., 18, 911 (2011).
- M. Kidwai, S. Kukreja and R. Thakur, Lett. Org. Chem., 3, 135 (2006).
- S. Caddick, Tetrahedron, 51, 10403 (1995).
- D. Dhabbi and C. Sharma, Indian J. Chem., 48B, 1006 (2009).
- S.S. Panda, P.V.R. Chaudhari and B.S. Jayshree, Indian J. Pharm. Sci., 6845 (2009).
- G. Bram, A. Loupy and M. Majdoub, Tetrahedron, 46, 5167 (1990).
- X. Guo, X. Qi and J. Chang, Acta Cryst., E62, 0374, (2006)
References
R. Preeti, V.K. Srivastava and K. Ashok, Eur. J. Med. Chem., 39, 449 (2004).
N. Siddiqui and M.S.A. Ahsan, Acta Pharm., 58, 445 (2008).
J.S. Biradar, B.S. Sasidhar and R. Parveen, Eur. J. Med. Chem., 45, 4074 (2010).
C. Mengchao, O. Masahiro, K. Hiroyuki, L.L. Bo and S. Hideo, Bioorg. Med. Chem. Lett., 21, 980 (2011).
S.S. Panda and P.V.R. Chaudhari, Indian J. Pharm. Sci., 70, 208 (2008).
U. Misra, A. Hitkari, A.K. Saxena, S. Gurtu and S. Shanker, Eur. J. Med. Chem., 31, 629 (1996).
S.Y. Hae, J.L. Eun, E.L. Jie, K.P. Woo, J.B. Du, S.C. Yong, Y.K. Hun, C. Hyunah and N.P. Ae, Bull. Korean. Chem. Soc., 30, 1873 (2009).
A. Padmaja, T. Payani, G.D. Reddy and V. Padmavathi, Eur. J. Med. Chem., 44, 4557 (2009).
T. Karthikeyan, V. Seelan, K.G. Lalitha and P.T. Perumal, Bioorg. Med. Chem. Lett., 19, 3370 (2009).
K.J. Ahmed, S. Reddy, M.J. Ramaiah, D.E. Dastagiri, V.M. Bharathi, A.F. Ameruddin, S.N.C.V.L. Pushpavalli, M. Pal-Bhadra, A. Juvekar, S. Sen and S. Zingde, Eur. J. Med. Chem., 45, 3924 (2010).
Y.R. Prasad, P.R. Kumar and B. Ramesh, Int. J. Chem. Sci., 5, 542 (2007).
S. Balachandran, P.K. Gadekar, S. Parkale, V.N. Yadav, D. Kamath, S. Ramaswamy, S. Sharma, R.A. Vishwakarma and N.M. Dagia, Bioorg. Med. Chem. Lett., 21, 1508 (2011).
G. Ahmad, P. Mishra, K. Mishra, P. Gupta, P.P. Yadav, P. Tiwari, A.K. Tamarkar, A.K. Srivastava and R. Maurya, Bioorg. Med. Chem. Lett., 15, 2139 (2006).
A.A.R. Mohamed and M.H.A. Eman, Monatsh. Chem., 140, 229 (2009).
T. Shah and V. Desai, J. Serb. Chem. Soc., 72, 443 (2007).
S.B. Lohiya and B.J. Ghiya, Indian J. Chem., 25B, 279 (1996).
S.R. Mohane, V.G. Thakare and B.N. Berad, Asian J. Chem., 21, 7422 (2009).
V. Tiwari, P. Ali and J. Meshram, Ultrasonics Sonochem., 18, 911 (2011).
M. Kidwai, S. Kukreja and R. Thakur, Lett. Org. Chem., 3, 135 (2006).
S. Caddick, Tetrahedron, 51, 10403 (1995).
D. Dhabbi and C. Sharma, Indian J. Chem., 48B, 1006 (2009).
S.S. Panda, P.V.R. Chaudhari and B.S. Jayshree, Indian J. Pharm. Sci., 6845 (2009).
G. Bram, A. Loupy and M. Majdoub, Tetrahedron, 46, 5167 (1990).
X. Guo, X. Qi and J. Chang, Acta Cryst., E62, 0374, (2006)