Russian Journal of Organic Chemistry

, volume 56 , issue 1 , pages 11-19

Beckmann Rearrangement of Oximes of the Fusidane Series

E V Salimova ¹

E V Tretyakova ¹

O S Kukovinets ²

L V Parfenova ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Ufa, Russia |

Bashkir State University, Ufa, Russia |

Publication type: Journal Article

Publication date: 2020-01-01

Pleiades Publishing

Russian Journal of Organic Chemistry

scimago Q4

wos Q4

SJR: 0.190

CiteScore: 1.3

Impact factor: 0.9

ISSN: 10704280, 16083393

DOI: 10.1134/S1070428020010030

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Organic Chemistry

Abstract

Reactions of 3,11-dioxo fusidane triterpenoids with hydroxylamine in anhydrous ethanol in the presence of a catalytic amount of 4-(dimethylamino)pyridine afforded hydroxyimino derivatives of fusidic acid with high chemo- and stereoselectivity. The products were isolated as pure (3Z,11E) isomers. Their rearrangement by the action of both acid and alkaline agents involved expansion of the A ring or both A and C rings of the triterpene skeleton with the formation of ε-lactam moieties as a result of first-order Beckmann rearrangement.

Found

2 citations

Parfenova Lyudmila

🥼 🤝

DSc in Chemistry, associate professor

110 publications, 1 039 citations, 8 reviews

h-index: 17

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

Regenerative materials

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GOST |

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Salimova E. V. et al. Beckmann Rearrangement of Oximes of the Fusidane Series // Russian Journal of Organic Chemistry. 2020. Vol. 56. No. 1. pp. 11-19.

GOST all authors (up to 50) Copy

Salimova E. V., Tretyakova E. V., Kukovinets O. S., Parfenova L. V. Beckmann Rearrangement of Oximes of the Fusidane Series // Russian Journal of Organic Chemistry. 2020. Vol. 56. No. 1. pp. 11-19.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1134/S1070428020010030

UR - https://doi.org/10.1134/S1070428020010030

TI - Beckmann Rearrangement of Oximes of the Fusidane Series

T2 - Russian Journal of Organic Chemistry

AU - Salimova, E V

AU - Tretyakova, E V

AU - Kukovinets, O S

AU - Parfenova, L V

PY - 2020

DA - 2020/01/01

PB - Pleiades Publishing

SP - 11-19

IS - 1

VL - 56

SN - 1070-4280

SN - 1608-3393

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2020_Salimova,

author = {E V Salimova and E V Tretyakova and O S Kukovinets and L V Parfenova},

title = {Beckmann Rearrangement of Oximes of the Fusidane Series},

journal = {Russian Journal of Organic Chemistry},

year = {2020},

volume = {56},

publisher = {Pleiades Publishing},

month = {jan},

url = {https://doi.org/10.1134/S1070428020010030},

number = {1},

pages = {11--19},

doi = {10.1134/S1070428020010030}

}

MLA

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MLA Copy

Salimova, E. V., et al. “Beckmann Rearrangement of Oximes of the Fusidane Series.” Russian Journal of Organic Chemistry, vol. 56, no. 1, Jan. 2020, pp. 11-19. https://doi.org/10.1134/S1070428020010030.