SYNTHESIS OF KETONES BASED ON OXIDATION OF ACETYLENE ALCOHOLS CONTAINING HALOGEN SUBSTITUTETS

  • Санъат САМАТОВ Университет экономики и педагогики, (PhD)
  • Одилжон ЗИЯДУЛЛАЕВ, Чирчикский государственный педагогический университет, (DSc)
  • Саида АБДУРАХМАНОВА,
  • Гузал ОТАМУХАМЕДОВА, Чирчикский государственный педагогический университет, (PhD)
  • Фарход БУРИЕВ, Чирчикский государственный педагогический университет, (преподаватель)
Keywords: oksidlanish, atsetilen spirti, keton, biologik faollik, xromatografiya, galogen o‘rinbosarlar.

Abstract

Synthesis of the corresponding ketones by oxidation of acetylene alcohols containing halogen substituents. The object of study was acetylene alcohols containing halogen substituents, including 1-(2-chlorophenyl)-3-phenylpropyn-2-ol-1 (1a), 1-(2,4-dichlorophenyl)-3-phenylpropyn-2-ol-1 (2a), 1-(4-bromophenyl)-3-phenylpropyn-2-ol-1 (3a) acetylene alcohols were selected. The oxidation process of acetylene alcohols 1a, 2a and 3a, chosen as the object of study, was carried out for the first time in open air without the presence of a catalyst. As a result, the corresponding ketones are formed, including 1-(2-chlorophenyl)-3-phenylpropyn-2-one-1 (1b), 1-(2,4-dichlorophenyl)-3-phenylpropyn-2-one-1 (2b) and 1-(4-bromophenyl)-3-phenylpropyn-2-one-1 (3b) were synthesized in various yields.

References

1. Bing Zh., Zhiyuan L., Feipeng L., Ynhua W., Junjian Sh., Qinghua B., Shicong H., Ming W. Highly Enantioselective Addition of Phenylethynylzinc to Aldehydes Catalyzed by Chiral Cyclopropane-Based Amino Alcohols. Molecules, 2013. 18, 15422-15433.
2. Ming N., Rui W., Zhi-jian H., Bin M., Chao-shan D., Lei L., Chao Ch. Synthesis of New C2-Symmetrical Bissulfonamide Ligands and Application in the Enantioselective Addition of Alkynylzinc to Aldehydes and Ketones. Adv. Synth. Catal. 2005, 347, 1659 – 1665.
3. Otamuxamedova, G.Q., Ziyadullayev O.E., Shmid E., Maniecki T. Enantioselective alkynylation of some cyclical ketones by 3,3′-diphenylbinaphtol dilithium. Chem. and Chem. Eng., 2019, 2, 30-36.
4. Wang Y., DuBois J., Hedman B., Hodgson K. Catalytic Galactose Oxidase Models: Biomimetic Cu(II)-Phenoxyl-Radical Reactivity. Science, 1998, 279, 537-540.
5. Que L. Jr., Tolman W.B. Biologically inspired oxidation catalysis. Nature, 2008, 455, 333-340.
6. Largeron M., Fleury M.B. Bioinspired Oxidation Catalysts. Science, 2013, 339, 43 – 44.
7. B. L. Ryland, S. S. Stahl. Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems. Angew. Chem. Int. Ed. 2014, 53, 8824 – 8838.
8. Allen S. E., Walvoord R. R., Padilla-Salinas R., Kozlowski M. C. Aerobic Copper-Catalyzed Organic Reactions. Chem. Rev. 2013, 113, 6234-6458.
9. Xu B., Lumb J., Arndtsen B. A TEMPO-Free Copper-Catalyzed Aerobic Oxidation of Alcohols. Angew. Chem. 2015, 127, 1-5.
10. Cainelli C., Cardillo C. Chromium Oxidants in Organic Chemistry. Springer, Berlin, 1984, 118.
11. Sato K., Aoki M., Noyori R., A "Green" Route to Adipic Acid: Direct Oxidation of Cyclohexenes with 30 Percent Hydrogen Peroxide. Science, 1998, 281. 1646.
12. Brink G.J., Isabel W., Arends C. E., Sheldon R.A. Green, Catalytic Oxidation of Alcohols in Water. Science. 2000, 287. 1636-1639.
13. Samatov S., Ikramov A., Abdurakhmanova S., Ziyadullayev O., Otamukhamedova G. Synthesis of aromatic acetylene alcohols based on benzaldehyde and its halogenated products benzaldehyde and its halogenated product. Chem. and Chem. Eng., 2022, 1, 42-48.
14. D. Filimonov, V. Poreykov. Forecast of the spectrum of biological activity of organic compounds. Rus. Сhem. J., 50/2, 66-75, 2006.
Published
2024-03-30
How to Cite
Санъат САМАТОВ, Одилжон ЗИЯДУЛЛАЕВ, Саида АБДУРАХМАНОВА, Гузал ОТАМУХАМЕДОВА, & Фарход БУРИЕВ,. (2024). SYNTHESIS OF KETONES BASED ON OXIDATION OF ACETYLENE ALCOHOLS CONTAINING HALOGEN SUBSTITUTETS. News of the NUUz, 3(3.1), 438-442. https://doi.org/10.69617/uzmu.v3i3.1.1870