PRODUCTION OF N-OXIDES OF PYRIDYLACETYLENE AMINES OBTAINED FROM 2-METHYL-5-ETHYNYLPYRIDINE
DOI:
https://doi.org/10.56122/..v2i2%20(26).420Keywords:
2-methyl-5-ethynylpyridine, methylamine, ethylamine, piperidine, morpholine, catalyst, solvents, pyridylacetylene amine N-oxides.Abstract
This work reports the investigation of reactions between 2-methyl-5-ethynylpyridine N-oxide and a range of aliphatic and aromatic amines, leading to the formation of pyridylacetylene amine N-oxides. The synthesis route involved the dehydrogenation of 2-methyl-5-ethylpyridine to yield 2-methyl-5-vinylpyridine, followed by bromination and dehydrobromination to afford 2-methyl-5-ethynylpyridine. Its oxidation with perhydrol in acetic anhydride provided 2-methyl-5-ethynylpyridine N-oxide. Subsequently, the Mannich reaction was employed for the preparation of N-oxides of pyridylacetylene amines. The effects of solvents (methanol, ethanol, and n-dioxane), the use of a catalyst, and reaction time on product yields were systematically examined. The structural features and composition of the synthesized pyridylacetylene amine N-oxides were confirmed through IR and PMR spectroscopic analysis.
References
Henry G.D. De novo syntehesis of substituted pyridines. Tetrahedron. 2004. V. 60. P. 6043-6061.
Drawbaugh, R., Bouffard, C., & Strauss, M. Synthesis and biological activity of 3,5-dinitro-4- and -2-(1H-purin-6-ylthio)benzoates, prodrugs of 6-mercaptopurine. Jour. Med. Chem. V. 19. No. 11. P. 1342–1345. doi:10.1021/jm00233a019.
Kurbanov A.I., B.A. Nosirova., Zokirov S., Sirlibaev T.S. Condensation of 2-methyl-5-ethynylpyridine with hexin-1-ol-3. Mater. Int. Conf. «III All-Union. Conf. by chemical reagents»Ashgabat. 1989.V. 3.P. 60.
Kurbanov A.I., Nosirova B.A. Condensation of 2-methyl-5-ethynylpyridine with 4-methyl-1-pentin-3-ol. Mater. Int. conf«I All-Union. Conf. in theoretical organic chemistry» Volgograd. 1991. P. 386. (in Russian).
Kurbanov A.I., Nosirova B.A. Oxidative condensation of 2-methyl-5-ethynylpyridine with pentin-1-ol-3. "Research in the field of organic chemistry and bioorganic chemistry" Collection of scientific papers. Tashkent State University of Tashkent. 1992. P. 34.
Ikramov A., Khalikova S.J., IkramovaSh.A. Synthesis of pyridine bases based on acetylene alcohols. Chemistry and Chem. Technology. 2018. No. 3. P. 37-40.
Ikramov A., Khalikova S.J., MusulmanovN.Kh.,KadirovKh.I., D.A. Handamov. Heterogeneous-catalytic synthesis of pyridine bases from acetylene, dimethyl ketone and ammonia. Chemistry and Chem. Technology. 2017. No. 1. P. 23-26.
Kadirov Kh.I., Akramov D.A., Turabzhanov S.M., Ikramov A. Catalytic synthesis of alkylpyridines. Chemistry and Chem. Technology. 2014. No. 2. P. 19-22.
Turabzhanov S.M., Ikramov A., KadirovKh.I.,Ruziev D.U., B.B. Gofurov. Some aspects of the selection of catalysts for heterophasic addition of HXmolecules to acetylene. Int. Сonf. «Catalytic processes of oil refining, petrochemicals and ecology»Tashkent. 2013. P. 29-30.
Shaker Y. Recekttrends in the chemistry of pyridine N-oxides Arсh. Org. Chem. 2001. P. 242-268. doi.org/10.3998/ark.5550190.0002.116.
Nivedita Chaudhri., Ray J. Butcherb and MuniappanSankar. Synthesis and structural, photophysical, electrochemical redox and axial ligation properties of highly electron deficient perchlorometalloporphyrins and selective CN sensing by Co(II) complexes.New J. Chem. 2018. V. 42. P. 8190-8199. DOI: 10.1039/c7nj04418f.
Ryzhakhov A.V., Alekseeva O.O., Rodina L.L. New trends in the chemistry of molecular complexes of heteroaromatic N-oxides. Bull. St. Peter. University. 2009. Ser. 4. Iss.1. P. 68-76.
Ryzakhov F.V., Fndreev V.P. Coordination of pyridine N-oxides with cations of alkali and alkaline earth metals. J. Gen. Chem. 2005.V. 75. No. 1. P. 133-136.
Collado D., Perez Inestrosa E.,Suau R., Desvergne J.P., BouasLaurent H. A new type of metal cation dual channel flnorosensor. Jour.Org. Lett.2002. V. 4. N. 5. P. 855-858.
SubramaniaRanganathan., Ch. ChandrashekharRao.,Suvarchala Devi Vudayagiri., Ybrd Rajeshаnd B. Jagadeesh.Solubilization of silica: Synthesis, characterization and study of penta-coordinated pyridine N-oxide silicon complexes.J. Chem. Sci. Vol. 116. No. 3. 2004.P. 169–174.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2025 Bulletin of the Osh State Pedagogical University named after A. Myrsabekova
This work is licensed under a Creative Commons Attribution 4.0 International License.
This work is licensed under the Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ or send a letter to Creative Commons, PO Box 1866, Mountain View, CA 94042, USA.
