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Nikolay S. Zefirov - One of the best experts on this subject based on the ideXlab platform.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles.
The Journal of organic chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
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unexpected Heterocyclization of electrophilic alkenes by tetranitromethane in the presence of triethylamine synthesis of 3 nitroisoxazoles
Journal of Organic Chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Per Bruheim, Nikolay S. ZefirovAbstract:Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their Heterocyclization, and the reactions proceed in an unusual way. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5‑Nitroisoxazoles
2019Co-Authors: Yulia A. Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed
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Heterocyclization of gem -dichlorocyclopropanes: “Fine tuning” of reactivity towards nitronium triflate
Tetrahedron Letters, 2017Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Victor B. Rybakov, Julia V. Kolodyazhnaya, D. V. Steglenko, Vladimir I. Minkin, Nikolay S. ZefirovAbstract:Abstract The Heterocyclization of gem -dichlorocyclopropanes upon treatment with nitronium triflate in organic nitriles was studied and the influence of the medium on the reaction pathway was shown. While in anhydrous solvent 5-chloroisoxazole was the only product, the admixture with water promoted a three-component Heterocyclization affording 4-chloropyrimidine N -oxides. This phenomenon was rationalized using DFT calculations.
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Three-component Heterocyclization of gem-bromofluorocyclopropanes with NOBF4: access to 4-fluoropyrimidine N-oxides.
The Journal of organic chemistry, 2012Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Andrei G. Kutateladze, Victor B. Rybakov, Nikolay S. ZefirovAbstract:Novel three-component Heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the Heterocyclization are discussed.
Elena B Averina - One of the best experts on this subject based on the ideXlab platform.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles.
The Journal of organic chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
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unexpected Heterocyclization of electrophilic alkenes by tetranitromethane in the presence of triethylamine synthesis of 3 nitroisoxazoles
Journal of Organic Chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Per Bruheim, Nikolay S. ZefirovAbstract:Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their Heterocyclization, and the reactions proceed in an unusual way. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5‑Nitroisoxazoles
2019Co-Authors: Yulia A. Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed
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Heterocyclization of gem -dichlorocyclopropanes: “Fine tuning” of reactivity towards nitronium triflate
Tetrahedron Letters, 2017Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Victor B. Rybakov, Julia V. Kolodyazhnaya, D. V. Steglenko, Vladimir I. Minkin, Nikolay S. ZefirovAbstract:Abstract The Heterocyclization of gem -dichlorocyclopropanes upon treatment with nitronium triflate in organic nitriles was studied and the influence of the medium on the reaction pathway was shown. While in anhydrous solvent 5-chloroisoxazole was the only product, the admixture with water promoted a three-component Heterocyclization affording 4-chloropyrimidine N -oxides. This phenomenon was rationalized using DFT calculations.
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Three-component Heterocyclization of gem-bromofluorocyclopropanes with NOBF4: access to 4-fluoropyrimidine N-oxides.
The Journal of organic chemistry, 2012Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Andrei G. Kutateladze, Victor B. Rybakov, Nikolay S. ZefirovAbstract:Novel three-component Heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the Heterocyclization are discussed.
Tamara S. Kuznetsova - One of the best experts on this subject based on the ideXlab platform.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles.
The Journal of organic chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
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unexpected Heterocyclization of electrophilic alkenes by tetranitromethane in the presence of triethylamine synthesis of 3 nitroisoxazoles
Journal of Organic Chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Per Bruheim, Nikolay S. ZefirovAbstract:Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their Heterocyclization, and the reactions proceed in an unusual way. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5‑Nitroisoxazoles
2019Co-Authors: Yulia A. Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed
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Heterocyclization of gem -dichlorocyclopropanes: “Fine tuning” of reactivity towards nitronium triflate
Tetrahedron Letters, 2017Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Victor B. Rybakov, Julia V. Kolodyazhnaya, D. V. Steglenko, Vladimir I. Minkin, Nikolay S. ZefirovAbstract:Abstract The Heterocyclization of gem -dichlorocyclopropanes upon treatment with nitronium triflate in organic nitriles was studied and the influence of the medium on the reaction pathway was shown. While in anhydrous solvent 5-chloroisoxazole was the only product, the admixture with water promoted a three-component Heterocyclization affording 4-chloropyrimidine N -oxides. This phenomenon was rationalized using DFT calculations.
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Three-component Heterocyclization of gem-bromofluorocyclopropanes with NOBF4: access to 4-fluoropyrimidine N-oxides.
The Journal of organic chemistry, 2012Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Andrei G. Kutateladze, Victor B. Rybakov, Nikolay S. ZefirovAbstract:Novel three-component Heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the Heterocyclization are discussed.
Yuri K Grishin - One of the best experts on this subject based on the ideXlab platform.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles.
The Journal of organic chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
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unexpected Heterocyclization of electrophilic alkenes by tetranitromethane in the presence of triethylamine synthesis of 3 nitroisoxazoles
Journal of Organic Chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Per Bruheim, Nikolay S. ZefirovAbstract:Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their Heterocyclization, and the reactions proceed in an unusual way. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5‑Nitroisoxazoles
2019Co-Authors: Yulia A. Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed
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Heterocyclization of gem -dichlorocyclopropanes: “Fine tuning” of reactivity towards nitronium triflate
Tetrahedron Letters, 2017Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Victor B. Rybakov, Julia V. Kolodyazhnaya, D. V. Steglenko, Vladimir I. Minkin, Nikolay S. ZefirovAbstract:Abstract The Heterocyclization of gem -dichlorocyclopropanes upon treatment with nitronium triflate in organic nitriles was studied and the influence of the medium on the reaction pathway was shown. While in anhydrous solvent 5-chloroisoxazole was the only product, the admixture with water promoted a three-component Heterocyclization affording 4-chloropyrimidine N -oxides. This phenomenon was rationalized using DFT calculations.
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Three-component Heterocyclization of gem-bromofluorocyclopropanes with NOBF4: access to 4-fluoropyrimidine N-oxides.
The Journal of organic chemistry, 2012Co-Authors: Kseniya N Sedenkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Andrei G. Kutateladze, Victor B. Rybakov, Nikolay S. ZefirovAbstract:Novel three-component Heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the Heterocyclization are discussed.
Yuliya A Volkova - One of the best experts on this subject based on the ideXlab platform.
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Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles.
The Journal of organic chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Kseniya N Sedenkova, Yuri K Grishin, Elena B Averina, Dmitry A Vasilenko, Per Bruheim, Nikolay S. ZefirovAbstract:A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the Heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, nitro, and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 5-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic proposal are discussed.
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unexpected Heterocyclization of electrophilic alkenes by tetranitromethane in the presence of triethylamine synthesis of 3 nitroisoxazoles
Journal of Organic Chemistry, 2019Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Per Bruheim, Nikolay S. ZefirovAbstract:Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their Heterocyclization, and the reactions proceed in an unusual way. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
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Unexpected Heterocyclization of electrophilic alkenes by tetranitromethane in the presence of triethylamine. Synthesis of 3-nitroisoxazoles.
The Journal of organic chemistry, 2010Co-Authors: Yuliya A Volkova, Tamara S. Kuznetsova, Yuri K Grishin, Elena B Averina, Per Bruheim, Nikolay S. ZefirovAbstract:Novel reaction of tetranitromethane (TNM) with electrophilic alkenes in the presence of triethylamine yielding substituted 3-nitroisoxazoles was found and studied. Triethylamine increases the reactivity of TNM toward electrophilic alkenes promoting their Heterocyclization, and the reactions proceed in an unusual way. A variety of alpha,beta-unsaturated aldehydes, ketones, esters, amides, phosphonates, and nitro and sulfur compounds was involved in the Heterocyclization reaction, and a wide range of functionalized 3-nitroisoxazoles was obtained in good to high yields. The scope and limitations of the reaction and the mechanistic aspects are discussed.
