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Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides. / Khlebnikov, Alexander F.; Tomashenko, Olesya A.; Funt, Liya D.; Novikov, Mikhail S.

в: Organic and Biomolecular Chemistry, Том 12, № 34, 2014, стр. 6598-6609.

Результаты исследований: Научные публикации в периодических изданиях › статья

Harvard

Khlebnikov, AF, Tomashenko, OA, Funt, LD & Novikov, MS 2014, 'Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides', Organic and Biomolecular Chemistry, Том. 12, № 34, стр. 6598-6609. https://doi.org/10.1039/C4OB00865K, https://doi.org/10.1039/c4ob00865k

APA

Khlebnikov, A. F., Tomashenko, O. A., Funt, L. D., & Novikov, M. S. (2014). Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides. Organic and Biomolecular Chemistry, 12(34), 6598-6609. https://doi.org/10.1039/C4OB00865K, https://doi.org/10.1039/c4ob00865k

Vancouver

Khlebnikov AF, Tomashenko OA, Funt LD, Novikov MS. Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides. Organic and Biomolecular Chemistry. 2014;12(34):6598-6609. https://doi.org/10.1039/C4OB00865K, https://doi.org/10.1039/c4ob00865k

Author

Khlebnikov, Alexander F. ; Tomashenko, Olesya A. ; Funt, Liya D. ; Novikov, Mikhail S. / Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides. в: Organic and Biomolecular Chemistry. 2014 ; Том 12, № 34. стр. 6598-6609.

BibTeX

@article{aa1da1d7f77f4004a9cf648cd62fd318,
title = "Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides",
abstract = "A domino reaction of 2H-azirines with 1-alkyl-3-phenacyl-1H-imidazolium bromides in the presence of Et3N provides a facile route to 1-alkyl-3-(1H-pyrrol-3-yl)-1H-imidazol-3-ium bromides. 1-Benzyl derivatives can be reduced to 1-(1H-pyrrol-3-yl)-1H-imidazoles with HCO2NH 4 on Pd/C. The action of KOH on pyrrolylimidazolium salts leads to a new type of stable ylide, 3-(1H-imidazol-3-ium-3-yl)-pyrrol-1-ides, which can, in principle, be in tautomeric equilibrium with the corresponding N-heterocyclic carbene. Although, according to the DFT B3LYP/6-31G(d) calculations in vacuo, electron-donating substituents in the 2-aryl-group cause the tautomeric equilibrium to shift to the carbene side, the investigated compounds exist in the ylide form in solution and in the solid state, which is in agreement with the relative stabilities of the species calculated with the PCM solvent model. This journal is {\textcopyright} the Partner Organisations 2014.",
author = "Khlebnikov, {Alexander F.} and Tomashenko, {Olesya A.} and Funt, {Liya D.} and Novikov, {Mikhail S.}",
year = "2014",
doi = "10.1039/C4OB00865K",
language = "English",
volume = "12",
pages = "6598--6609",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "34",

}

RIS

TY - JOUR

T1 - Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides

AU - Khlebnikov, Alexander F.

AU - Tomashenko, Olesya A.

AU - Funt, Liya D.

AU - Novikov, Mikhail S.

PY - 2014

Y1 - 2014

N2 - A domino reaction of 2H-azirines with 1-alkyl-3-phenacyl-1H-imidazolium bromides in the presence of Et3N provides a facile route to 1-alkyl-3-(1H-pyrrol-3-yl)-1H-imidazol-3-ium bromides. 1-Benzyl derivatives can be reduced to 1-(1H-pyrrol-3-yl)-1H-imidazoles with HCO2NH 4 on Pd/C. The action of KOH on pyrrolylimidazolium salts leads to a new type of stable ylide, 3-(1H-imidazol-3-ium-3-yl)-pyrrol-1-ides, which can, in principle, be in tautomeric equilibrium with the corresponding N-heterocyclic carbene. Although, according to the DFT B3LYP/6-31G(d) calculations in vacuo, electron-donating substituents in the 2-aryl-group cause the tautomeric equilibrium to shift to the carbene side, the investigated compounds exist in the ylide form in solution and in the solid state, which is in agreement with the relative stabilities of the species calculated with the PCM solvent model. This journal is © the Partner Organisations 2014.

AB - A domino reaction of 2H-azirines with 1-alkyl-3-phenacyl-1H-imidazolium bromides in the presence of Et3N provides a facile route to 1-alkyl-3-(1H-pyrrol-3-yl)-1H-imidazol-3-ium bromides. 1-Benzyl derivatives can be reduced to 1-(1H-pyrrol-3-yl)-1H-imidazoles with HCO2NH 4 on Pd/C. The action of KOH on pyrrolylimidazolium salts leads to a new type of stable ylide, 3-(1H-imidazol-3-ium-3-yl)-pyrrol-1-ides, which can, in principle, be in tautomeric equilibrium with the corresponding N-heterocyclic carbene. Although, according to the DFT B3LYP/6-31G(d) calculations in vacuo, electron-donating substituents in the 2-aryl-group cause the tautomeric equilibrium to shift to the carbene side, the investigated compounds exist in the ylide form in solution and in the solid state, which is in agreement with the relative stabilities of the species calculated with the PCM solvent model. This journal is © the Partner Organisations 2014.

U2 - 10.1039/C4OB00865K

DO - 10.1039/C4OB00865K

M3 - Article

VL - 12

SP - 6598

EP - 6609

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 34

ER -

ID: 5702082