European Journal of Chemistry

Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

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Published: Dec 22, 2010
DOI: https://doi.org/10.5155/eurjchem.1.4.302-306.185
Keywords:
1, 3, 5-Triazines, Alkylation, Transesterification, Hydroxamic acids, Synthesis
Section
Research Article
Issue
Vol. 1 No. 4 (2010): December 2010
Dates
Received 2010-06-25
Accepted 2010-10-07
Published 2010-12-22


Main Article Content

Svetlana Mikhaylichenko
Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
Olga Kvak
Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
Shadi Dalili
Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
Vladimir Zaplishny
Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada

Abstract

A convenient method for synthesis of new sym-triazine ester and hydroxamate derivatives has been developed. Various reaction conditions were studied and optimized, and a series of new 1,3,5-triazine based esters and N-hydroxyamides were obtained with good yields (38-80%). The reaction between oxo-derivatives of 4,6-disubstituted-1,3,5-triazines and halogenated carboxylic esters derivatives using  Cs2CO3 as a catalyst was found to be the most convenient method for 4,6-disubstituted-1,3,5-triazine-2-yloxy esters  synthesis. These 1,3,5-triazin based esters served as precursors for the synthesis of 4,6-disubstituted-1,3,5-triazin-2-yloxy-N-hydroxybutanamides using solution of hydroxylamine hydrochloride in dry methanol and KOH at room temperature.  Structures of the newly synthesized compounds were obtained by 1H NMR, 13C NMR, MS, IR spectral data and elemental analysis.

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Mikhaylichenko, S.; Kvak, O.; Dalili, S.; Zaplishny, V. Synthesis of New 4,6-Disubstituted-1,3-5-Triazin-2-Yloxy Esters and N-Hydroxyamides. Eur. J. Chem. 2010, 1, 302-306.

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References

[1]. Knuniants I. Chem. Encyclopedia, 5th edition, v. 1, Sovietskaya encyclopedia Publishing House, Moscow, 1988.

[2]. Fazary, A. E.; Khalil, M. M.; Fahmy, A.; Tantawy, T. A. Medical Journal of Islamic Academy of Sciences, 2001, 14(3), 109-116.

[3]. Dooley, C. M.; Devocelle, M.; McLoughlin, K. B.; Nolan, K. B.; Fitzgerald, D. J.; Sharkey, C. T. Mol. Pharmacol. 2003, 63(2), 450-455.
doi:10.1124/mol.63.2.450
PMid:12527817

[4]. Nigović, B.; Kujundžić, N.; Sanković, K.; Vikić-Topić, D. Acta Chim. Slov. 2002, 49(3), 525-535.

[5]. Nirmal, K.; Huber, V.; Smith, P.; Gopalan, A. Tetrahedron, 1994, 50(9), 2657-2664.
doi:10.1016/S0040-4020(01)86981-7

[6]. Huang, L.; Pardee, A. B. Mol. Medicine, 2000, 6(10), 849-866.
PMid:11126200    PMCid:1949918

[7]. Taylor, R. Czech. J. Phys. 1999, 49, 617-623.
doi:10.1007/s10582-999-1041-0

[8]. Matijevic, J.; Samarzija, I.; Honovic, L.; Jurisic, B. Acta Pharm. 2008, 58, 231-236.
doi:10.2478/v10007-008-0010-7
PMid:18515233

[9]. Kobashi, K.; Takebe, S.; Terashima, N.; Hase, J. J. Biochem. 1975, 77, 837-843.

[10]. Mishra, H.; Parrill, A. L.; Williamson, J. S. Antimicrob. Agents Chemother. 2002, 46(8), 2613-2618.
doi:10.1128/AAC.46.8.2613-2618.2002
PMid:12121941    PMCid:127352

[11]. Emanuele, S.; Lauricella, M.; Tesoriere, G. Int. J. Oncol. 2008, 33(4), 637-646.
PMid:18813776

[12]. Massaro, A.; Mordini, A.; Reginato, G.; Russo, F.; Taddei M. Synthesis. 2007, 20, 3201-3204.

[13]. Ning, L.; Greenblatt, D. Y.; Kunnimalaiyaan, M.; Chen, H. Oncologist, 2008, 13(2), 98-104.
doi:10.1634/theoncologist.2007-0190
PMid:18305053

[14]. Niemeyer, H. M. Euphytica, 1988, 37(3), 289-293.

[15]. Zasada, I.; Meer, S.; Halbrendt, J.; Rice C. Nematology, 2005, 95, 1116-1121.

[16]. Holland, K. P.; Elford, H. L.; Bracchi, V.; Annis, C. G.; Schuster, S. M.; Chakrabarti, D. Antimicrob. Agents Chemother. 1998, 42(9), 2456-2458.
PMid:9736585    PMCid:105855

[17]. Blotny, G. Tetrahedron, 2006, 62(41), 9507-9522.
doi:10.1016/j.tet.2006.07.039

[18]. Smolin, E.; Rappoport, L. s-Triazine and Derivatives, Interscience, NY, 1959.

[19]. Melnikov, N.; Bascakov, Y. Chemistry of Herbicides and Growth Regulators of Plants, Goskhimizdat Publishing House, Moscow, 1962.

[20]. Pogosian, G.; Pankratov, V.; Zaplishny, V.; Matsoyan, S.; Korshak, V. Polytriazines, Armenian SSR Academy of Sciences Publishing House, Erevan, 1987.

[21]. Katritzky, A.; Rees, C.; Scriven, E.; Potts, K. Comprehensive Heterocyclic Chemistry, v. 5, Pergamon, Oxford, 1984.

[22]. Demirayak, S.; Karaburun, A. C.; Beis R. Eur. J. Med. Chem. 2004, 39(12), 1089-1095.
doi:10.1016/j.ejmech.2004.09.005
PMid:15571871

[23]. Antonian, S.; Zaplishny, V.; Pogosian, G.; Libinzon, R.; Lavretskaya, E.; Pijov, V.; Bessudnova, N.; Sarkisian, D.; Vatolkina O. Khimiko-Farmatsevticheskii Zhurnal 1986, 20(2), 172-175.

[24]. Mikhaylichenko, S.; Dounin, V.; Zaplishny, V. Effectivity of the PASS program in Predicting Biological Activity for sym-Triazine Derivatives. Fourth International Symposium on Computational Methods in Toxicology and Pharmacology Integrating Internet Resources, Moscow, Russia, September 1-5, 2007.

[25]. Mikhaylichenko, S.; Dounin, V.; Zaplishny, V.; Chesnyuk, A. Synthesis and Potential Bioactivity of New Pyrazolyl-sym-Triazine Derivatives. Fourth International Symposium on Computational Methods in Toxicology and Pharmacology Integrating Internet Resources, Moscow, Russia, September 1-5, 2007.

[26]. Chesnyuk, A.; Mikhaylichenko, S.; Konyushkin, L.; Kotlyarov, N.; Zaplishny, V. Patent RU, Chem. Abstr. 2005, 144, 22947.

[27]. Chesnyuk, A.; Mikhaylichenko, S.; Firgang, S.; Kotlyarov, N.; Zaplishny, V. Patent RU, Chem. Abstr. 2006, 144, 345097.

[28]. Chesnyuk, A.; Mikhaylichenko, S.; Konyushkin, L.; Kotlyarov, N.; Zaplishny, V. Patent RU, Chem. Abstr. 2005, 144, 345098.

[29]. Giacomelli, G.; Porcheddu, A.; Salaris, M. Org. Lett. 2003, 5(15), 2715-2717.
doi:10.1021/ol034903j
PMid:12868897

[30]. Bethel, W. J.; Rowayton, R. Patent US 4, 939, 213, Chem. Abstr. 1990.

[31]. Maffezzoni, R.; Zanda, M. Tetrahedron Let. 2008, 49(35), 5129-5132.
doi:10.1016/j.tetlet.2008.06.101

[32]. Anandan, S. K.; Ward, J. S.; Brokx, R. D.; Denny, T.; Bray, M. R.; Patel, D. V.; Xiao, X. Y. Bioorg. Med. Chem. Lett. 2007, 17(21), 5995-5999.
doi:10.1016/j.bmcl.2007.07.050

[33]. Hauser, C. R. Renfrow, W. B. Org. Synth. 1939, 19, 15-17.

[34]. Ho, C. Y.; Strobel, E.; Ralbovsky, J.; Galermo, R. A. J. Org. Chem. 2005, 70(12), 4873-4875.
doi:10.1021/jo050036f
PMid:15932334

[35]. Jones, L. W. and Hurd, C. D. J. Am. Chem. Soc. 1921, 43(11), 2422-2448.
doi:10.1021/ja01444a016

[36]. Chesnyuk, A.; Mikhaylichenko, S.; Zavodnov, V.; Zaplishny, V. Chem. Heterocycl. Compd. 2002, 38(2), 177-182.
doi:10.1023/A:1015335124677

[37]. Mikhaylichenko, S.; Chesnyuk, A.; Zavodnik, V.; Firgang, S.; Koniushkin L.; Zaplishny, V. Chem. Heterocycl. Compd. 2002, 38(3), 292-299.
doi:10.1023/A:1015631203046

[38]. Gordon, A. J.; Ford, R. A. The Chemist’s Companion. Handbook of Practical Data, Techniques, and References, John Wiley&Sons, 1973.

[39]. Jerry, R. M; Christina, N. H.; Paul, F. S. Techniques in Organic Chemistry, W. H. Freeman, 2006.

[40]. Mikhaylichenko, S.; Chesnyuk, A.; Konyushkin, L.; Zaplishny, V. Russ. Chem. Bull. 2003, 52(10), 2157-2160.
doi:10.1023/B:RUCB.0000011872.22319.7e

[41]. Chesnyuk, A.; Mikhaylichenko, S.; Konyushkin, L.; Firgang, S.; Zaplishny, V. Russ. Chem. Bull. 2005, 54(8), 1900-1906.
doi:10.1007/s11172-006-0056-y

[42]. Mikhaylichenko, S.; Chesnyuk, A.; Konyushkin, L.; Zaplishny, V. Chem. Heterocycl. Compd. 2006, 42(5), 642-647.
doi:10.1007/s10593-006-0140-0

[43]. Chesnyuk, A.; Mikhaylichenko, S.; Zaplishny, V.; Konyushkin, L.; Firgang, S.; Chem. Heterocycl. Compd. 2008, 44(3), 339-348.
doi:10.1007/s10593-008-0050-4

[44]. Vogel, A. J.; Tatchell, A. R.; Furnis, B. S.; Hannaford, A. J.; Smith, P. W. G. Vogel’s Textbook of Practical Organic Chemistry, 5th edition, Prentice Hall, 1996.

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