ПРОЦЕСС АЛКИНИЛИРОВАНИЯ НЕКОТОРЫХ ГЕТЕРОАТОМНЫХ АЛЬДЕГИДОВ С АЛКИНАМИ В ПРИСУСТВИИ КАТАЛИТИЧЕСКОЙ СИСТЕМЫ InBr3/Et3N/Et2O
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Альдегиды, содержащие в своей мoлекуле гетероатом‒ тиофен-2-карбальдегид, 3-метилтиофен-2-карбальдегид, фуран-2-карбальдегид, пиридин-3-карбальдегид, хинолин-2-карбальдегид и 3-бром-4 пиридинкарбальдегидов с ацетилен, фенилацетилен, гексин-1, октином-1 впервые были синтезированы ацетиленовые спирты с использованием каталитической системы InBr3/Et3N/Et2O. Систематически изучалось влияние молярных количественных соотношений исходных веществ, длительности реакции, температуры, природы катализатора и растворителей на выход продукта. Состав, чистота и структура синтезированных ацетиленовых спиртов нового поколения доказаны современными физико-химическими методами.
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A.R. Pandev, D.K. Tiwari, A. Prakhar, D.P. Mishra, S.K. Sharma A review towards synthesis of heterocycles using propargyl alcohols and propargyl amines // Monatsh Chemistry, 2022, Volume 153, pp. 383-407.
Surendra Puri Oxygen as a heteroatom in propargylic Alcohols: Reactivity, Selectivity and applications // Organic and Supramolecular chemistry, 2020, Volume 5, Issue 31, pp. 9866-9877.
Nikolai A. Sitte, Francesca Ghiringhelli, Grigory A. Shevchenko, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub Copper-Catalysed Synthesis of Propargyl Alcohol and Derivatives from Acetylene and other Terminal alkynes // Advanced Synthesis and Catalysis, 2022, Volume 364, Issue 13, pp. 2227-2234.
Fernando Martínez-Lara, Anisley Suárez, Noelia Velasco, Samuel Suárez-Pantiga, Roberto Sanz Gold-Catalyzed Reactions of 2-Alkynyl-1-indolyl-1,2-diols with Thiols: Stereoselective Synthesis of (Z)-α-Indol-3-yl α-(2-Thioalkenyl) Ketones // Advanced Synthesis and Catalysis, 2022, Volume 364, pp. 132-138.
En Gao, Qiao Li, Lili Duan, Lin Li, Yue-Ming Li Isosterically designed chiral catalysts: Rationale, optimization and their application in enantioselective nucleophilic addition to aldehydes // Tetrahedron, 2020, Volume 76, pp. 1316-1324.
Nadezhda M. Vitkovskaya, Vladimir B. Orel, Vladimir B. Kobychev, Alexander S. Bobkov, Elena Yu. Larionova, Boris A. Trofimov Exploring acetylene chemistry in superbasic media: A theoretical study of the effect of water on vinylation and ethynylation reactions with acetylene in KOH/DMSO and NaOH/DMSO systems // Journal of Physical Organic Chemistry, 2017, Volume 30, Issue 8, pp. 3669-3682.
Shoko Nagahata, Seiya Takei, Satoshi Ueno One-Pot Synthesis of Multiarylated Benzophenonnes via [3+2+1] Benzannulation of Ketones, Alkynes and α,β-Unsaturated Carbonyls // Journal Organic Chemistry, 2022, Volume 87, Issue 15, pp. 10377-10384.
Idris Karakaya, Semistan Karabuga, Ramazan Altundas, Sabri Ulukanli Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes // Tetrahedron, 2014, Volume 70, pp. 8385-8388.
Ji-Cai, Zhou Lei Zhao, Yuan Li, Ding-Qiang Fu, Zi-Cheng Li, Wen-Cai Huang. Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of propargylic alcohols // Research on Chemical Intermediates, 2017, Volume 43, pp. 4283-4294.
E. Yu. Shmidt, I. A. Bidusenko, N. I. Protsuk, A. I. Mikhaleva, and B. A. Trofimov Improved Synthesis of Tertiary Propargyl Alcohols by the Favorskii Reaction of Alkyl Aryl (Hetaryl) Ketones with Acetylene // Russian Journal of Organic Chemistry, 2013, Volume 49, Issue 1, pp. 8-17.
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.
Francis Mariaraj Irudayanathan, Jimin Kim, Kwang Ho Song, Sunwoo Lee Transition-Metal-Free Decarboxylative Coupling Reactions for the Synthesis of Propargyl Alcohols // Asian Journal of Organic Chemistry, 2016, Volume 5, pp. 1148-1154.
Nadezhda M. Vitkovskaya, Vladimir B. Orel, Vladimir B. Kobychev, Alexander S. Bobkov, Damir Z. Absalyamov, Boris A. Trofimov Quantum-chemical models of KOH(KOBut)/DMSO superbasic systems and mechanisms of base-promoted acetylene reactions // International Journal Quantum Chemistry, 2020, Volume 120, Isuue 26158, pp. 12-23.
Аbduraxmanova Saida, Ziyadullaev Odiljon, Ikramov Аbduvahob, Saliyeva Muyassar Synthesis of aromatic acetylene alcohols on the basis of various aldehydes in the catalytic system ZnEt2/TI(OiPr)4 // Journal of Critical Reviews, 2020, Volume 7, Issue 19, pp. 1488-1499.
Аblakulov Lochinbek Kuchkorovich, Ikramov Аbduvaxab, Ziyadullaev Odiljon Egamberdievich, Otaqoʼziev Dilshod Do‘ltaxo‘ja o‘g‘li. Magniy organik birikmalar asosida aromatik atsetilen spirtlari sintezi // FarDU. Ilmiy habarlar, 2021, №6, 26-32 b.
Kang Y.F., Yang W.J. The use of bifunctional catalyst systems in the asymmetric addition of alkynylzinc to aldehydes// Abstract Journal Chemistry, 2005, Volume 48, pp. 112-119.
Lin Pu Asymmetric alkynylzinc additions to aldehydes and ketones // Tetrahedron, 2003, Volume 59, pp. 9873–9886.
Ryo Takita, Kenichiro Yakura, Takashi Ohshima, Masakatsu Shibasaki Asymmetric Alkynylation of Aldehydes Catalyzed by an In(III)/BINOL Complex // Journal of the American Chemical Society, 2005, Volume 127, Issue 40, pp. 13760-13761.