- Selective synthesis of 1-vinylpyrroles directly from ketones and acetylene: Modification of Trofimov reaction
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Consecutive treatment of ketones with a system NH2OH?HCl- NaHCO3-DMSO and acetylene excess in the presence of KOH (100-120°C, initial acetylene pressure 12-15 at) led to a selective formation of 2-and 2,3-substituted 1-vinylpyrroles
- Mikhaleva,Shmidt,Ivanov,Vasil'tsov,Senotrusova,Protsuk
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- FORMATION OF FREE RADICALS IN THE VINYLATION OF 2-SUBSTITUTED PYRROLES WITH ACETYLENES IN A KOH-DMSO SYSTEM
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By spin trapping, using 2-methyl-2-nitrosopropane (t-BuNO), the EPR signals of vinyl-tert-butyl-nitroxyls and spin adducts of t-BuNO with products of the addition of 2-substituted pyrrole radicals to acetylenes were recorded during the vinylation of 2-sub
- Vakul'skaya, T. I.,Trofimov, B. A.,Mikhaleva, A. I.,Korostova, S. E.,Shevchenko, S. G.,Sobenina, L. I.
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- NEW EXAMPLES OF THE VINYLATION OF NH-HETEROCYCLES WITH ACETYLENE AT ATMOSPHERIC PRESSURE IN THE KOH-DMSO SYSTEM
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Vinylation of 2-hetarylpyrroles, 4,5-dihydrobenzoindole, and 1,2,3,4-tetrahydro-γ-carbinols at atmospheric pressure in the superbasic system KOH-DMSO at 100-120 deg C has given the corresponding N-vinyl derivatives in yields of 92-99percent.
- Trofimov, B.A.,Nesterenko, R.N.,Mikhaleva, A.I.,Shapiro, A.B.,Aliev, I.A.,et. al.
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- Preparation and properties of co-oligomers of 1-vinyl-1,2,4-triazole with N-vinyl-2-phenylpyrrole
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Novel water-soluble co-oligomers of 1-vinyl-1,2,4-triazole and N-vinyl-2-phenylpyrrole have been prepared by radical copolymerization. Copolymerization constants of the monomers and the parameters of cooligomers microstructure have been determined. 1-Viny
- Ermakova,Korzhova,Kuznetsova,Mazyar,Larina,Pozdnyakov,Scherbakova,Mikhaleva,Prozorova
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- Direct synthesis of aryl substituted pyrroles from calcium carbide: An underestimated chemical feedstock?
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In this work, a novel synthetic methodology for the preparation of aryl pyrroles directly from the reaction of calcium carbide with oxime is reported. Various pyrrole derivatives are generated from the corresponding oximes in satisfactory yields (49–88%) under the optimized conditions. The one-pot synthesis of aryl pyrrole from widely available ketone is also successfully developed. A new near-infrared fluorescent BODIPY dye containing a phenyl substitution at the C-3 position is expediently prepared from the aryl pyrrole derived from this methodology. The key benefit of this methodology is the use of an inexpensive and less hazardous primary chemical feedstock, calcium carbide, in a wet solvent without any metal catalysts. This process offers a novel cost-efficient route for the synthesis of functionalized pyrrole.
- Kaewchangwat, Narongpol,Sukato, Rangsarit,Vchirawongkwin, Viwat,Vilaivan, Tirayut,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
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p. 460 - 465
(2018/04/16)
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- 2-phenylpyrrole: One-pot selective synthesis from acetophenone oxime and acetylene by a Trofimov reaction
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We have developed a technologically orientated, one-pot way of synthesis of high purity 2-phenylpyrrole in 74% yield by treatment of acetophenone oxime with acetylene in the KOH-DMSO system. The reaction is carried out at 135-150°C under an acetylene atmospheric pressure. The synthesis was performed in laboratory (glass apparatus) and in a large scale (10 l reaction vessel).
- Mikhaleva,Petrova,Sobenina
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p. 1367 - 1371
(2014/07/21)
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- Comparison of the electronic and steric structures of 1-vinyl-and 1-(prop-1-en-1-yl)pyrroles according to the 1H and 13C NMR data
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According to the 1H and 13C NMR data, 1-isopropenylpyrroles are characterized by larger dihedral angles between the heteroring and exocyclic double bond planes, as compared to isostructural 1-vinylpyrroles, due to steric effect of th
- Afonin,Ushakov,Simonenko,Tarasova,Maksimova,Trofimov
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p. 397 - 405
(2007/10/03)
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- Synthesis and thermal stability of O-vinylketoximes
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The O-vinylketoximes 2 were synthesized from ketoximes 1 and acetylene in superbase systems in good to excellent yields. Their thermal stability was investigated.
- Trofimov, Boris A.,Al'bina, Mikhaleva I.,Vasil'tsov, Alexander M.,Schmidt, Elena Yu.,Tarasova, Ol'ga A.,Morozova, Ludmila V.,Sobenina, Lubov' N.,Preiss, Thomas,Henkelmann, Jochem
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p. 1125 - 1132
(2007/10/03)
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- PYRROLES FROM KETOXIMES AND ACETYLENE. 44. METHYL ARYL KETOXIMES WITH REACTIVE SUBSTITUENTS
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The Trofinov reaction was extended to methyl aryl ketoximes with substituents in the benzene ring that are unstable with respect to the action of a strongly basic medium.The corresponding pyrroles and their 1-vinyl derivatives were obtained. 4-Nitroacetophenone oxime, from which only 2-phenyl- and 1-phenyl-2-phenylpyrrole were obtained, and 4-bromoacetophenone oxime, the reaction of which leads to the formation of 1-vinyl-2-(4-vinyloxyphenyl)pyrrole in addition to the principal 2-(4-bromophenyl)pyrrole, constituted exceptions.
- Korostova, S. E.,Shevchenko, S. G.,Sigalov, M. V.
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p. 151 - 155
(2007/10/02)
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- EFFECT OF THE STRUCTURE OF PYRROLES ON THEIR VINYLATION RATE
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The rate nucleophilic vinylation of pyrroles by acetylene (100 deg C, DMSO, = 1.5 M, = 0.5 M) decreases with increase in their acidity (with decrease in the basicity of the anions).Sterically screened pyrroles (2,5-diphenylpyrrole) deviate
- Trofimov, B. A.,Korostova, S. E.,Shevchenko, S. G.,Polubentsev, E. A.,Mikhaleva, A. I.
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p. 956 - 959
(2007/10/02)
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- EVIDENCE OF SINGLE-ELECTRON TRANSFER IN THE VINYLATION OF PYRROLES BY ACETYLENE
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The vinylation of 2-phenylpyrrole and 4,5,6,7-tetrahydroindole by acetylene in the KOH-DMSO system is retarded by typical inhibitors of radical processes (hydroquinone, benzophenone, nitroxyl radicals).This indicates the presence of a single-electron tran
- Trofimov, B. A.,Korostova, S. E.,Shevchenko, S. G.,Mikhaleva, A. I.
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p. 807 - 810
(2007/10/02)
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- PYRROLES FROM KETOXIMES AND ACETYLENE. 39. EFFECT OF THE NATURE OF THE ALKALI METAL CATION AND THE SOLVENT ON THE REACTION RATE IN MOH-DMSO SYSTEMS
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The principal tendencies of the effect of the nature of the cation of the hydroxide (Li+, Na+, K+, Rb+, Cs+), and the solvent (DMSO, hexamethylphosphoric triamide (HMPT), 1-methyl-2-pyrrolidone, sulfolane, DMF, polyethylene glycol, hydrazine hydrate, tetramethylurea), and the additive (cesium and rubidium salts and linear macrocyclic polyethers) in the KOH-DMSO catalytic system on the processes involved in the pyrrolization of acetophenone oxime with acetylene and the vinylation of the resulting 2-phenylpyrrole were ascertained.
- Korostova, S. E.,Shevchenko, S. G.,Polubentsev, E. A.,Mikhaleva, A. I.,Trofimov, B. A.
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p. 635 - 638
(2007/10/02)
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- PYRROLES FROM KETOXIMES AND ACETYLENE. 28. INVESTIGATION OF VINYL CHLORIDE INSTEAD OF ACETYLENE FOR THE SYNTHESIS OF ARYLPYRROLES FROM ARYLETHANONE OXIMES
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2-Arylpyrroles and their N-vinyl derivatives have been synthesized by reacting arylethanone oximes with vinyl chloride in a KOH-DMSO system at 140 deg C.
- Aliev, I. A.,Almamedova, D. T.,Gasanov, B. R.,Mikhaleva, A. I.
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p. 1117 - 1119
(2007/10/02)
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