Abstract:
Reaction between isopropyl phenyl ketoxime and acetylene in the KOH–DMSO–n-hexane system (70°C, ∼ 5min), along with known 3,3-dimethyl-2-phenyl-3H-pyrrole (51% yield) and 4,4-dimethyl-5-phenyl-1-vinyl-2-pyrrolidinone (7% yield), affords also unexpected 2-(2-ethynyl-3,3-dimethyl-2-phenyl-1-aziranyl)-4,4-dimethyl-5-phenyl-3,4-dihydro-2H-pyrrole (4% yield).
Document Type:
Article
Language: English
Citation:
D. A. Shabalin, T. E. Glotova, I. A. Ushakov, M. Yu. Dvorko, A. V. Vashchenko, V. I. Smirnov, E. Yu. Schmidt, A. I. Mikhaleva, B. A. Trofimov, “2-(2-Ethynyl-1-aziranyl)-3,4-dihydro-2H-pyrrole: a one-pot assembly from isopropyl phenyl ketoxime and acetylene during the synthesis of 3H-pyrrole”, Mendeleev Commun., 24:6 (2014), 368–369
Linking options:
https://www.mathnet.ru/eng/mendc2585
https://www.mathnet.ru/eng/mendc/v24/i6/p368
This publication is cited in the following 5 articles:
D. A Shabalin, “sec-Alkylketoximes in the Trofimov reaction: from minor products to reagents of the XXI century”, Žurnal organičeskoj himii, 59:10 (2023), 1251
D. A. Shabalin, “Secondary Alkyl Ketoximes in the Trofimov Reaction: From Minor Products to 21st Century Reagents”, Russ J Org Chem, 59:10 (2023), 1645
Vladimir V. Voronin, Maria S. Ledovskaya, Alexander S. Bogachenkov, Konstantin S. Rodygin, Valentine P. Ananikov, “Acetylene in Organic Synthesis: Recent Progress and New Uses”, Molecules, 23:10 (2018), 2442
Mikhail Yu. Belikov, Oleg V. Ershov, “Synthesis of 3H-pyrroles (microreview)”, Chem Heterocycl Comp, 52:5 (2016), 279
Dmitrii A. Shabalin, Tatyana E. Glotova, Igor A. Ushakov, Marina Yu. Dvorko, Alexander V. Vashchenko, Vladimir I. Smirnov, Elena Yu. Schmidt, Al'bina I. Mikhaleva, Boris A. Trofimov, “ChemInform Abstract: 2‐(2‐Ethynyl‐1‐aziranyl)‐3,4‐dihydro‐2H‐pyrrole (III): A One‐Pot Assembly from Isopropyl Phenyl Ketoxime and Acetylene During the Synthesis of 3H‐Pyrrole (IV).”, ChemInform, 46:18 (2015)
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