SYNTHESIS OF ACETYLENE ALCOHOLS BASED ON ENANTIOSELECTIVE ETHYNYLATION OF KETONES WHICH HAVE VARIOUS NATURE

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Sarvinoz Tirkasheva
Odiljon Ziyadullayev
Valentin Nenaydenko
Qo‘shboqov Farrux Zokir o‘g‘li Qo‘shboqov Farrux Zokir o‘g‘li

Abstract

For the first time, terminal acetylene alcohols were synthesized by the enantioselective ethynylation reaction of some ketones using calcium carbide in the TBAF·3H2O/DMSO/H2O catalytic system. The influence of the nature and amounts of solvents, catalysts, reagents and substrates on product yield was studied. The most alternative conditions of control and direction of reactions are determined. The series of product formation efficiency of selected ketones was developed. Synthesized terminal acetylene alcohols were identified, their composition, purity, structure and specific constants were proved by modern physico-chemical methods.

Article Details

How to Cite
Tirkasheva , S., Ziyadullayev , O., Nenaydenko , V., & Qo‘shboqov Farrux Zokir o‘g‘li, Q. F. Z. o‘g‘li. (2023). SYNTHESIS OF ACETYLENE ALCOHOLS BASED ON ENANTIOSELECTIVE ETHYNYLATION OF KETONES WHICH HAVE VARIOUS NATURE. Scientific Journal of the Fergana State University, 29(3), 138. Retrieved from https://journal.fdu.uz/index.php/sjfsu/article/view/2604
Section
Chemistry
Author Biographies

Sarvinoz Tirkasheva , Chirchik State Pedagogical University

Chirchiq davlat pedagogika universiteti, Fizika va kimyo fakulteti, kimyo kafedrasi tayanch doktoranti

Odiljon Ziyadullayev , Chirchik State Pedagogical University

Chirchiq davlat pedagogika universiteti, ilmiy ishlar va innovatsiyalar bo‘yicha prorektori, kimyo fanlari doktori, professor

Valentin Nenaydenko , Moscow State University

Moskva davlat universiteti, Kimyo fakulteti, organik kimyo kafedrasi mudiri, kimyo fanlari doktori, professor

Qo‘shboqov Farrux Zokir o‘g‘li Qo‘shboqov Farrux Zokir o‘g‘li, Chirchik State Pedagogical University

Chirchiq davlat pedagogika universiteti, Fizika va kimyo fakulteti, kimyo kafedrasi tayanch doktoranti

References

Surabhi Mishra, Sindoori R. Nair, Beeraiah Baire Recent approaches for the synthesis of pyridines and (iso)quinolones using propargylic Alcohols // Organic Biomolecular Chemistry, 2022, Volume 20, Issue 31, pp. 6037-6056.

Chenxiao Qian, Meiwen Liu, Jianwei Sun, Pengfei Li Chiral phosphoric acid-catalyzed region- and enantioselective reactions of functionalized propargylic alcohols // Organic Chemistry Frontiers, 2022, Volume 9, Issue 5, pp. 1234-1240.

George Wu, Mingsheng Huang Organolithium Reagents in Pharmaceutical Asymmetric Processes // Chemical Reviews, 2006, Volume 206, Issue 7, pp. 2596-2616.

F. Diederich, P.J. Stang, R.R. Tykwinski Acetylene Chemistry: – Weinheim.: Wiley-VCH, 2005 – pp. 120-380.

Xiaoxiang Zhang, Wan Teng Teo, Sally, Philip Wai Hong Chan Bronsted Acid Catalyzed Cyclization of Propargylic Alcohols with Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles // Journal of Organic chemistry, 2010, Volume 75, Issue 18, pp. 6290-6293.

Kaluvu Balaraman, Venkitasamy Kesavan Efficient Copper (II) Acetate Catalyzed Homo- and Heterocoupling of Terminal Alkynes at Ambient Conditions // Synthesis, 2010, No. 20, pp. 3461-3466.

Shunsuke Kotani, Kenji Kukita, Kana Tanaka, Tomonori Ichibakase, Makoto Nakajima Lithium Binaphtholate-Catalyzed Asymmetric Addition of Lithium Acetylides to Carbonyl Compounds //Journal of Organic Chemistry, 2014, Volume 79, Issue 11, pp. 4817-4825.

Semistan Karabuga, Idris Karakaya, Sabri Ulukanli 3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes // Tetrahedron: Asymmetry, 2014, Volume 25, pp. 851-855.

Emil Lindback, You Zhou, Lavinia Marinescu, Christian M. Pedersen, Mikael Bols The Grignard Reaction of Cyclodextrin-6-aldehydes Revisited: A study of the Streoselectivity upon Addition of Organometallic reagents to aldehydes and ketones // European Journal of Organic Chemistry, 2010, Issue 20, pp. 3883-3896.

Y. N. Sum, D. Yu, Y. Zhang Synthesis of acetylene alcohols with calcium carbide as the acetylene source // Green Chemistry, 2013, Volume 15, Issue 10, pp. 2718-2721.

D. Wang, Z. Liu, Q. Liu One-Pot Synthesis of Methyl-Substituted Benzenes and Methyl-Substituted Naphthalenes from Acetone and Calcium Carbide // Industrial and Engineering Chemistry Research, 2019, Volume 58, Issue 16, pp. 6226-6234.

Zheng Li, Lili He, Rugang Fu, Geyang Song, Wenli Song, Demeng Xie and Jingya Yang Using Calcium Carbide as an Acetylene Source: Synthesis of 1,3,5-Triaroylcyclohexanes // Tetrahedron, 2016, Volume 72, Issue 29, pp. 4321-4328.

Yoon Kyung Jang, Marc Magre, Magnus Rueping Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis // Organic Letters, 2019, Volume 21, Issue 20, pp. 8349-8352.

Gabriella Barozzino-Consiglio, Yi Yuan, Catherine Fressigne, Anne Harrison-Marchand, Hassan Oulyadi, Jacques Maddaluno Enantioselective Alkynylation of Aldehydes by Mixed Aggregates of 3 Aminopyrrolidine Lithium Amides and Lithium Acetylides //Organometallics, 2015, Volume 34, Issue 18, pp. 4441-4450.

Elena Yu. Schmidt, Natalia A. Cherimichkina, Ivan A. Bidusenko, Nadezhda I. Protzuk, Boris A. Trofimov Alkynylation of Aldehydes and Ketones Using the Bu4NOH/H2O/DMSO Catalytic Composition: A Wide-Scope Methodology // European journal of organic chemistry, 2014, Volume 2014, Issue 21, pp. 4663-4670.

Torsten Weil, Peter R. Schreiner Organocatalytic Alkynylation of Aldehydes and Ketones under Phase-Transfer Catalytic Conditions // European journal of organic chemistry, 2005, Volume 2005, Issue 11, pp. 2213-2217.

Junfeng Liu, Jin Lin, Ling Song Efficient catalytic transition-metal-free conditions for nucleophilic addition of arylacetylenes to aromatic ketones // Tetrahedron Letters, 2012, Volume 53, Issue 17, pp. 2160-2163.

Abolfazl Hosseini, Afsaneh Pilevar, Eimear Hogan, Boris Mogwitz, Anne S. Schulze, Peter R. Schreiner Calcium Carbide Catalytically Activated with Tetra-n-butyl Ammonium Fluoride for Sonogashira Cross Coupling Reactions // Organic & Biomolecular Chemistry, 2017, Volume 15, Issue 32, -pp. 6800-6807.

Тиркашева С., Салиева М., Зиядуллаев О. Айрим кетонларни кальций карбид асосида этиниллаш // УзМУ хабарлари, 2022, № 3(2), 448-452 б.

Hui-Yin-Li, Haoran-Sun, Stephen Dimagno Tetra-n-butylammonium Fluoride. Encyclopedia of Reagents for Organic Synthesis, 2007, pp. 1-9.

Haoran Sun, Stephen G. DiMagno "Anhydrous Tetrabutylammonium Fluoride". Journal of the American Chemical Society, 2005, 127 (7) pp. 2050-2051. doi:10.1021/ja0440497.

Jacques Muzart N,N-Dimethylformamide: much more than a solvent // Tetrahedron, 2009, № 65, pp. 8313-8323.

Josefredo R. Pliego Jr, Jose M. Riveros Gibbs energy of solvation of organic ions in aqueous and dimethyl sulfoxide solutions // Physical Chemistry Chemical Physics, 2002, Volume 4, Issue 9, pp. 1622-1627.

Alhadji Malloum, Jeanet Conradie Solvation free energy of the proton in acetonitrile // Journal of Molecular Liquids, 2021, Volume 335, № 116032, pp. 1-8.

Abdurakhmanova S.S., Ziyadullaev О.E., Otamukhamedova G.Q., Parmanov A.B. Еnantioselective alkinylation reactions of some aldehydes by catalytic systems based on titanium tetraisopropyloxide // O‘zbekiston kimyo jurnali, 2021, №3, 53-64 b.