Synthesis of 1,2,3-Triazole Derivatives Based on Propargyl Ester of a Saturated Single-Basic Carbonic Acid and ParaAzidobenzoic Acid
Keywords:
course, inflammatory, presence, catalystAbstract
The development of highly effective and low-toxicity nonsteroidal anti-inflammatory drugs (NSAIDs) is one of the important challenges facing modern pharmacology. To overcome this problem, many studies have been conducted on compounds containing a five-membered heterocycle containing three nitrogen atoms. The pharmacodynamics of these compounds are mainly due to their anti-inflammatory effect. Therefore, it is important to synthesize new derivatives of 1,2,3-triazoles, to determine their structure and to look for substances with anti-inflammatory activity on their basis. For the first time, the corresponding derivatives of 4-(4-(exchangeable)-1H-1,2,3-triazole-1-yl)-benzoic acid were synthesized by cycloaddition of propargyl esters of saturated carboxylic acids and para-azidobenzoic acid in the presence of copper (I) iodide. The structure of the obtained substances was analyzed by IR, 1H NMR, and MS techniques. It is proved that under the action of the catalyst in the reaction, only 1,4-isomers are formed. Factors affecting the course of the reaction were identified.
References
Griess, J. P. Proc. R. Soc. Lond. 1864, 13, 375–384.
. Ustinov, A. V.; Stepanova, I. A.; Dubnyakova, V. V.; Zasepin, T. S.;
Nojevnikova, E. V.; Korshun V. A. Bioorganicheskaya Ximiya 2010, 4,
-481.
. Stefaniak, M.; Jasinski, M.; Urbaniak, K.; Romanski, J. Chemik. 2014, 68
(7), 592-599.
. Huisgen, R. Proc. Chem. Soc. 1961, 357-396.
. Huisgen, R.; Pawda, A. (Editors) 1,3-Dipolar Cycloaddition Chemistry;
John Wiley & Sons, Ltd.: New York, NY, USA, 1984.
. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40
(11), 2004–2021.
. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker,
C. J. Chem. Rev. 2009, 109 (11), 5620–5686.
. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew.
Chem. Int. Ed. 2002, 41 (14), 2596–2599.
. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67 (9),
–3064.
. Huisgen, R. Angew. Chem. Int. Ed. Engl. 1963, 2 (10), 565–598.
. Liang, L.; Astruc, D. Coord. Chem. Rev. 2011, 255 (23–24), 2933–2945.
. Astruc, D.; Liang, L.; Rapakousiou, A.; Ruiz, J. Acc. Chem. Res. 2011, 45
(4), 630–640.
. Wang, X.; Huang, B.; Liu, X.; Zhan, P. Drug Discovery Today 2016, 21
(1), 118–132.
Downloads
Published
Issue
Section
License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
User Rights
Under the Creative Commons Attribution-NonCommercial 4.0 International (CC-BY-NC), the author (s) and users are free to share (copy, distribute and transmit the contribution).
Rights of Authors
Authors retain the following rights:
1. Copyright and other proprietary rights relating to the article, such as patent rights,
2. the right to use the substance of the article in future works, including lectures and books,
3. the right to reproduce the article for own purposes, provided the copies are not offered for sale,
4. the right to self-archive the article.
