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Alexander F. Khlebnikov - One of the best experts on this subject based on the ideXlab platform.
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fe ii catalyzed isomerization of 5 chloroisoxazoles to 2h azirine 2 carbonyl chlorides as a key stage in the synthesis of pyrazole nitrogen heterocycle dyads
Journal of Organic Chemistry, 2018Co-Authors: Kirill I Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields.
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Fe(II)-Catalyzed Isomerization of 5‑Chloroisoxazoles to 2H‑Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole–Nitrogen Heterocycle Dyads
2018Co-Authors: Kirill I. Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields
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Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2‑Dihydropyrimidines
2018Co-Authors: Alexander N. Koronatov, Alexander F. Khlebnikov, Nikolai V. Rostovskii, Mikhail S. NovikovAbstract:A high yield synthesis of 1,2-dihydropyrimidines by the Rh(II)-catalyzed reaction of diazocarbonyl compounds with 1,4-di- and 1,4,5-trisubstituted Pyrazoles is reported. This reaction represents the first example of a carbenoid insertion into a N–N bond and provides a novel approach to 4-unsubstituted 1,2-dihydropyrimidines with a broad range of functional group tolerance. According to DFT calculations, the pyrazole ring expansion proceeds via the sequential formation of the metal-bound pyrazolium ylide, metal-free pyrazolium ylide, and 1,5-diazahexatriene followed by 1,6-cyclization
Kirill I Mikhailov - One of the best experts on this subject based on the ideXlab platform.
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fe ii catalyzed isomerization of 5 chloroisoxazoles to 2h azirine 2 carbonyl chlorides as a key stage in the synthesis of pyrazole nitrogen heterocycle dyads
Journal of Organic Chemistry, 2018Co-Authors: Kirill I Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields.
Mikhail S. Novikov - One of the best experts on this subject based on the ideXlab platform.
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fe ii catalyzed isomerization of 5 chloroisoxazoles to 2h azirine 2 carbonyl chlorides as a key stage in the synthesis of pyrazole nitrogen heterocycle dyads
Journal of Organic Chemistry, 2018Co-Authors: Kirill I Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields.
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Fe(II)-Catalyzed Isomerization of 5‑Chloroisoxazoles to 2H‑Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole–Nitrogen Heterocycle Dyads
2018Co-Authors: Kirill I. Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields
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Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2‑Dihydropyrimidines
2018Co-Authors: Alexander N. Koronatov, Alexander F. Khlebnikov, Nikolai V. Rostovskii, Mikhail S. NovikovAbstract:A high yield synthesis of 1,2-dihydropyrimidines by the Rh(II)-catalyzed reaction of diazocarbonyl compounds with 1,4-di- and 1,4,5-trisubstituted Pyrazoles is reported. This reaction represents the first example of a carbenoid insertion into a N–N bond and provides a novel approach to 4-unsubstituted 1,2-dihydropyrimidines with a broad range of functional group tolerance. According to DFT calculations, the pyrazole ring expansion proceeds via the sequential formation of the metal-bound pyrazolium ylide, metal-free pyrazolium ylide, and 1,5-diazahexatriene followed by 1,6-cyclization
Chaoguo Yan - One of the best experts on this subject based on the ideXlab platform.
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diastereoselective synthesis of spiro indene 2 2 pyrazolo 1 2 a Pyrazoles and spiro indoline 3 2 pyrazolo 1 2 a Pyrazoles via 1 3 dipolar cycloaddition
RSC Advances, 2016Co-Authors: Jing Sun, Yanhong Jiang, Chaoguo YanAbstract:The 1,3-dipolar cycloaddition of cyclic azomethine imines with 2-arylideneindene-1,3-diones in refluxing acetonitrile afforded predominately cis-1,3-diaryl-substituted spiro[indene-2,2′-pyrazolo[1,2-a]pyrazole] derivatives in good yields. Significantly, the similar cycloaddition reaction of cyclic azomethine imines with 3-phenacylideneoxindoles gave polysubstituted spiro[indoline-3,2′-pyrazolo[1,2-a]Pyrazoles] in good yields and with high diastereoselectivity.
Alexey V. Galenko - One of the best experts on this subject based on the ideXlab platform.
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fe ii catalyzed isomerization of 5 chloroisoxazoles to 2h azirine 2 carbonyl chlorides as a key stage in the synthesis of pyrazole nitrogen heterocycle dyads
Journal of Organic Chemistry, 2018Co-Authors: Kirill I Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields.
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Fe(II)-Catalyzed Isomerization of 5‑Chloroisoxazoles to 2H‑Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole–Nitrogen Heterocycle Dyads
2018Co-Authors: Kirill I. Mikhailov, Ekaterina E. Galenko, Mikhail S. Novikov, Alexey V. Galenko, Alexander Yu. Ivanov, Galina L. Starova, Alexander F. KhlebnikovAbstract:2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with Pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole–nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-Pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360–410 nm with high quantum yields
