Copyright (c) 2017 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
An Easy Procedure for Synthesis of 1,3,4-Oxadiazines: A Potential Antimicrobial Agents
Corresponding Author(s) : Ajay Kumar Kariyappa
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
An efficient and accessible procedure for the synthesis of 1,3,4-oxadiazines was developed. Reaction involves the cyclocondensation of phenylhydrazones catalyzed by a mild base triethylamine to produce 1,3,4-oxadiazines in good yields. The synthesized new compounds were characterized by spectral studies and elemental analyses and were screened to explore in vitro antimicrobial activity against bacteria and fungi species. The compounds displayed good to excellent potency against tested microorganisms, in particular, compound with chloro substitution showed good antimicrobial potential.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M. Baumann and I.R. Baxendale, Beilstein J. Org. Chem., 9, 2265 (2013); https://doi.org/10.3762/bjoc.9.265.
- Y. Luo and G. Yang, Bioorg. Med. Chem. Lett., 15, 1716 (2007); https://doi.org/10.1016/j.bmc.2006.12.002.
- Y. Higashio and T. Shoji, Appl. Catal. A, 260, 251 (2004); https://doi.org/10.1016/S0926-860X(03)00197-2.
- (a) D.L. Trepanier, P.E. Krieger and J.N. Eble, J. Med. Chem., 8, 802 (1965); https://doi.org/10.1021/jm00330a016. (b) M. Bakavoli, M. Rahimizadeh, A. Shiri and H. Eshghi, Heterocycl. Commun., 17, 49 (2011).
- J. van Alphen, Recl. Trav. Chim. Pays Bas, 47, 673 (1928); https://doi.org/10.1002/recl.19280470805.
- J. van Alphen, Recl. Trav. Chim. Pays Bas, 47, 909 (1928); https://doi.org/10.1002/recl.19280471105.
- W.J. Hoppenbrouwers, Recl. Trav. Chim. Pays Bas, 53, 325 (1934); https://doi.org/10.1002/recl.19340530405.
- S. Zen and K. Harada, Chem. Lett., 11, 1711 (1982); https://doi.org/10.1246/cl.1982.1711.
- P.T. Berkowitz, R.A. Long, P. Dea, R.K. Robins and T.R. Matthews, J. Med. Chem., 20, 134 (1977); https://doi.org/10.1021/jm00211a028.
- R.M. Mohareb, R.A. Ibrahim and H.E. Moustafa, Open Org. Chem. J., 4, 8 (2010); https://doi.org/10.2174/1874095201004010008.
- J.S. Biradar and S.Y. Manjunath, Indian J. Chem., 43B, 389 (2004).
- H. Sano, T. Noguchi, A. Miyajima, Y. Hashimoto and H. Miyachi, Bioorg. Med. Chem. Lett., 16, 3068 (2006); https://doi.org/10.1016/j.bmcl.2006.02.021.
- H. Xu, W.Q. Liu, L.L. Fan, Y. Chen, L.M. Yang, L. Lv and Y.T. Zheng, Chem. Pharm. Bull. (Tokyo), 56, 720 (2008); https://doi.org/10.1248/cpb.56.720.
- R.P. Robinson and K.M. Donahue, J. Heterocycl. Chem., 31, 1541 (1994); https://doi.org/10.1002/jhet.5570310644.
- (a) P. Jayaroopa, G. Vasanth Kumar, N. Renuka, M.A. Harish Nayaka and K. Ajay Kumar, Int. J. PharmTech. Res., 5, 264 (2013); (b) P. Jayaroopa, G. Vasanth Kumar, N. Renuka, M.A. Harish Nayaka, K. Ajay Kumar, Int. J. PharmTech. Res., 5, 819 (2013).
- V.K. Govindappa, J. Prabhashankar, B.A. Khatoon, M.B. Ningappa and A.K. Kariyappa, Der Pharma Chem., 4, 2283 (2012).
References
M. Baumann and I.R. Baxendale, Beilstein J. Org. Chem., 9, 2265 (2013); https://doi.org/10.3762/bjoc.9.265.
Y. Luo and G. Yang, Bioorg. Med. Chem. Lett., 15, 1716 (2007); https://doi.org/10.1016/j.bmc.2006.12.002.
Y. Higashio and T. Shoji, Appl. Catal. A, 260, 251 (2004); https://doi.org/10.1016/S0926-860X(03)00197-2.
(a) D.L. Trepanier, P.E. Krieger and J.N. Eble, J. Med. Chem., 8, 802 (1965); https://doi.org/10.1021/jm00330a016. (b) M. Bakavoli, M. Rahimizadeh, A. Shiri and H. Eshghi, Heterocycl. Commun., 17, 49 (2011).
J. van Alphen, Recl. Trav. Chim. Pays Bas, 47, 673 (1928); https://doi.org/10.1002/recl.19280470805.
J. van Alphen, Recl. Trav. Chim. Pays Bas, 47, 909 (1928); https://doi.org/10.1002/recl.19280471105.
W.J. Hoppenbrouwers, Recl. Trav. Chim. Pays Bas, 53, 325 (1934); https://doi.org/10.1002/recl.19340530405.
S. Zen and K. Harada, Chem. Lett., 11, 1711 (1982); https://doi.org/10.1246/cl.1982.1711.
P.T. Berkowitz, R.A. Long, P. Dea, R.K. Robins and T.R. Matthews, J. Med. Chem., 20, 134 (1977); https://doi.org/10.1021/jm00211a028.
R.M. Mohareb, R.A. Ibrahim and H.E. Moustafa, Open Org. Chem. J., 4, 8 (2010); https://doi.org/10.2174/1874095201004010008.
J.S. Biradar and S.Y. Manjunath, Indian J. Chem., 43B, 389 (2004).
H. Sano, T. Noguchi, A. Miyajima, Y. Hashimoto and H. Miyachi, Bioorg. Med. Chem. Lett., 16, 3068 (2006); https://doi.org/10.1016/j.bmcl.2006.02.021.
H. Xu, W.Q. Liu, L.L. Fan, Y. Chen, L.M. Yang, L. Lv and Y.T. Zheng, Chem. Pharm. Bull. (Tokyo), 56, 720 (2008); https://doi.org/10.1248/cpb.56.720.
R.P. Robinson and K.M. Donahue, J. Heterocycl. Chem., 31, 1541 (1994); https://doi.org/10.1002/jhet.5570310644.
(a) P. Jayaroopa, G. Vasanth Kumar, N. Renuka, M.A. Harish Nayaka and K. Ajay Kumar, Int. J. PharmTech. Res., 5, 264 (2013); (b) P. Jayaroopa, G. Vasanth Kumar, N. Renuka, M.A. Harish Nayaka, K. Ajay Kumar, Int. J. PharmTech. Res., 5, 819 (2013).
V.K. Govindappa, J. Prabhashankar, B.A. Khatoon, M.B. Ningappa and A.K. Kariyappa, Der Pharma Chem., 4, 2283 (2012).