European Journal of Chemistry 2010, 1(4), 302-306 | doi: https://doi.org/10.5155/eurjchem.1.4.302-306.185 | Get rights and content

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


Svetlana Mikhaylichenko (1,*) , Olga Kvak (2) , Shadi Dalili (3) , Vladimir Zaplishny (4)

(1) Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
(2) Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
(3) Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
(4) Department of Physical and Environmental Sciences, University of Toronto Scarborough, Toronto, ON-M1C 1A4, Canada
(*) Corresponding Author

Received: 25 Jun 2010 | Revised: 02 Nov 2010 | Accepted: 07 Oct 2010 | Published: 22 Dec 2010 | Issue Date: December 2010

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.

1_4_302_306_800


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Keywords


1,3,5-Triazines; Alkylation; Transesterification; Hydroxamic acids; Synthesis

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DOI: 10.5155/eurjchem.1.4.302-306.185

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Citations

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[1]. Vigen G. Barkhudaryan, Gayane V. Ananyan, Yeva B. Dalyan, Samvel G. Haroutiunian
Development of viscometric methods for studying the interaction of various porphyrins with DNA. Part I: meso-tetra-(4N-hydroxyethylpyridyl) porphyrin and its Ni-, Cu-, Co- and Zn- containing derivatives
Journal of Porphyrins and Phthalocyanines  18(07), 594, 2014
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[2]. Song Mi Bae, Sung Young Kang, Ju Hyun Song
Synthesis and Cytotoxic Activity of Hexahydro‐1,3,5‐triazine Derivatives through Ring Condensation
Bulletin of the Korean Chemical Society  42(6), 840, 2021
DOI: 10.1002/bkcs.12266
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How to cite


Mikhaylichenko, S.; Kvak, O.; Dalili, S.; Zaplishny, V. Eur. J. Chem. 2010, 1(4), 302-306. doi:10.5155/eurjchem.1.4.302-306.185
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(4), 302-306. doi:10.5155/eurjchem.1.4.302-306.185
Mikhaylichenko, S., Kvak, O., Dalili, S., & Zaplishny, V. (2010). Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides. European Journal of Chemistry, 1(4), 302-306. doi:10.5155/eurjchem.1.4.302-306.185
Mikhaylichenko, Svetlana, Olga Kvak, Shadi Dalili, & Vladimir Zaplishny. "Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides." European Journal of Chemistry [Online], 1.4 (2010): 302-306. Web. 4 Jun. 2023
Mikhaylichenko, Svetlana, Kvak, Olga, Dalili, Shadi, AND Zaplishny, Vladimir. "Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

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