S. F. Vasilevskii, M. P. Davydova, V. I. Mamatyuk, N. V. Pleshkova, D. S. Fadeev, I. V. Alabugin, “Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond via formal internal redox process”, Mendeleev Commun., 25:5 (2015), 377

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Mendeleev Communications, 2015, Volume 25, Issue 5, Pages 377–379
DOI: https://doi.org/10.1016/j.mencom.2015.09.021 (Mi mendc2415)

This article is cited in 8 scientific papers (total in 8 papers)

Communications

Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond via formal internal redox process

S. F. Vasilevskii^ab, M. P. Davydova^a, V. I. Mamatyuk^bc, N. V. Pleshkova^c, D. S. Fadeev^c, I. V. Alabugin^d

^a V.V. Voevodsky Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^b Novosibirsk State University, Novosibirsk, Russian Federation
^c N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^d Department of Chemistry, Florida State University, Tallahassee, USA

Full-text PDF (264 kB) Citations (8)

DOI: https://doi.org/10.1016/j.mencom.2015.09.021

Graphic abstract: Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond <i>via</i> formal internal redox process

Abstract: Reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with (+)-pseudoephedrine leads to products of alkyne moiety cleavage, namely, 1-(3,4,5-trimethoxyphenyl)ethanone and N-(1-hydroxy-1-phenylprop-2-yl)-N-methylbenzamides. In the course of the process one of alkyne carbons undergoes a formal reduction to a Me group, whereas the other one is oxidized to a C(O)NRR’ moiety.

Document Type: Article

Language: English

*Supplementary materials:*
		Supplementary_data_1.pdf	(346.3 Kb)

Citation: S. F. Vasilevskii, M. P. Davydova, V. I. Mamatyuk, N. V. Pleshkova, D. S. Fadeev, I. V. Alabugin, “Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond via formal internal redox process”, Mendeleev Commun., 25:5 (2015), 377–379

Linking options:

https://www.mathnet.ru/eng/mendc2415

https://www.mathnet.ru/eng/mendc/v25/i5/p377

This publication is cited in the following 8 articles:

Asrar Ahmad, Shakir Ali Siddiqui, Priya Tyagi, Lokesh Gupta, Kshatresh Dutta Dubey, Ajoy Kapat, “The Role of the Carbonyl Group in C–C Triple Bond Cleavage of Ynones via Grob-Type Fragmentation under Acidic Conditions”, J. Org. Chem., 2025
Xianrong Cai, Jie Xiang, Jia Zheng, Juan Tang, Jian Su, Chunru Cheng, “One-Pot Synthesis of 1,3-Diketones from Alkynones with the Assistance of Imidazole”, Russ J Org Chem, 60:7 (2024), 1198
S. F. Vasilevsky, A. A. Stepanov, “Alkyl, Aryl, and Hetaryl Acetylenes: Highly Reactive Multifunctional Compounds (A Review)”, Russ J Gen Chem, 93:10 (2023), 2417
S. F Vasilevsky, A. A Stepanov, “Alkyl, aryl and hetaryl acetylenes - highly reactive multifunctional compounds (a review)”, Žurnal obŝej himii, 93:10 (2023), 1479
Igor V. Alabugin, Edgar Gonzalez-Rodriguez, Rahul Kisan Kawade, Aleksandr A. Stepanov, Sergei F. Vasilevsky, “Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry”, Molecules, 24:6 (2019), 1036
Carmen Nájera, Leiv K. Sydnes, Miguel Yus, “Conjugated Ynones in Organic Synthesis”, Chem. Rev., 119:20 (2019), 11110
Alexey R. Romanov, Alexander Yu. Rulev, Igor A. Ushakov, Vasiliy M. Muzalevskiy, Valentine G. Nenajdenko, “One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF3‐Ynones”, Eur J Org Chem, 2017:28 (2017), 4121
Maria P. Davydova, Sergey F. Vasilevsky, Valentine G. Nenajdenko, “Reaction of trifluoroacetyl acetylenes with β-amino alcohols. Synthesis of enaminoketones and unusual fragmentation”, Journal of Fluorine Chemistry, 190 (2016), 61

Citing articles in Google Scholar: Russian citations, English citations
Related articles in Google Scholar: Russian articles, English articles

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