Abstract:
2-Acetyl-3,4-dihydropyrans bearing 2-, 4- and 6-positioned aryl and alkyl groups, available from acetylene and ketones, undergo easy deacetylation in the KOBut/DMSO system (100 °C, 1.5 h) to give 2,4,6-trisubstituted dihydropyrans.
Citation:
E. Yu. Schmidt, I. V. Tatarinova, I. A. Ushakov, B. A. Trofimov, “2,4,6-Trisubstituted 3,4-dihydropyrans from acetylene and ketones: deacetylation in the KOBut/DMSO system”, Mendeleev Commun., 28:2 (2018), 145–146
Linking options:
https://www.mathnet.ru/eng/mendc1693
https://www.mathnet.ru/eng/mendc/v28/i2/p145
This publication is cited in the following 6 articles:
Elena Yu. Schmidt, Ivan A. Bidusenko, Nadezhda I. Protsuk, Igor A. Ushakov, Boris A. Trofimov, “Concise assembly of 7-ethynyl-6,8-dioxabicyclo[3.2.1]octanes from acetylenes and ketones”, Org. Biomol. Chem., 21:15 (2023), 3183
E. Yu. Schmidt, B. A. Trofimov, “Acetylene in Organic Synthesis. From the Chaos of Small Molecules to Highly Organized Structures. A Review”, Dokl Chem, 505:1 (2022), 127
E. Yu. Schmidt, N. V. Semenova, E. V. Ivanova, I. A. Ushakov, B. A. Trofimov, “Multimolecular self-organization of acetylene and arylamines into 1-aryl-3-ethyl-4-vinylpyrroles in the KOBut/DMSO system”, Mendeleev Commun., 30:3 (2020), 315–317
E. Yu. Schmidt, N. V. Semenova, I. A. Ushakov, A. V. Vashchenko, B. A. Trofimov, “Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps”, Mendeleev Commun., 29:1 (2019), 17–18
Elena Y. Schmidt, Inna V. Tatarinova, Nadezhda V. Semenova, Nadezhda I. Protsuk, Igor' A. Ushakov, Boris A. Trofimov, “Exploring Acetylene Chemistry: A Transition Metal-Free Route to Dienyl 6,8-Dioxabicyclo[3.2.1]octanes from Ketones and Acetylenes”, J. Org. Chem., 83:17 (2018), 10272
E. Yu. Schmidt, I. A. Bidusenko, I. A. Ushakov, B. A. Trofimov, “Unfolding the frontalin chemistry: a facile selective hydrogenation of 7-methylidene-6,8-dioxabicyclo[3.2.1]octanes, 2:2 ensembles of ketones and acetylene”, Mendeleev Commun., 28:5 (2018), 513–514
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