Tetrahedron

, volume 72 , issue 51 , pages 8493-8501

Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation

Dmitry Tatarinov ^{1, 2}

Denis M Kuznetsov ^{1, 2}

A. D. Voloshina ¹

Anna P Lyubina ^{1, 2}

Anastasiya S Strobykina ¹

Fahima K Mukhitova ³

Fedor M Polyancev ¹

Valery L. Mironov ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, Kazan, 420088, Russian Federation

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Kazan Scientific Center of the Russian Academy of Sciences

Kazan Federal University, Kremlevskaya Str. 18, Kazan, 420008, Russian Federation |

Kazan Institute of Biochemistry and Biophysics, Russian Academy of Sciences, Lobachevsky Str. 2/31, Kazan, 420111, Russian Federation |

Publication type: Journal Article

Publication date: 2016-12-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2016.11.023

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

A new two-step synthesis of phosphonium salts from phosphine oxides using Grignard reagents is reported. This approach involves a cyclization of Z- dialkyl-(diaryl)[2-(5-chloro-2-hydroxyphenyl)-2-phenylvinyl]phosphine oxides under the action of sulfinyl chloride with the formation of 2,2-dialkyl(diaryl)-6-chloro-4-phenyl-2 H -1,2-benzoxaphosphinin-2-ium chlorides followed by ring opening under the action of organomagnesium compounds. The method was successfully applied to prepare a series of a new phosphonium salts bearing phenolic moiety with a wide range of substituents at phosphorus atom. Synthesized phosphonium salts shows high antibacterial and antifungal in vitro activity and low toxicity towards human red blood cell.

Found

3 citations

Islamov Daut

PhD

168 publications, 1 549 citations

h-index: 20

Kazan Scientific Center of the Russian Academy of Sciences

Research interests

X-ray diffraction analysis

2 citations

Zakharova Lucia

DSc in Chemistry, professor

394 publications, 6 131 citations

h-index: 36

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

1 citation

Voronina Julia

131 publications, 1 116 citations

h-index: 18

Plekhanov Russian University of Economics

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

1 citation

Fayzullin Robert

🥼 🤝

185 publications, 1 841 citations, 49 reviews

h-index: 22

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

1 citation

Vasilyeva Leysan

PhD in Chemistry

29 publications, 491 citations

h-index: 14

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Colloidal chemistry

Drug delivery systems

Physical Chemistry

Surfactants

1 citation

Vasilieva Elmira

PhD in Chemistry

48 publications, 698 citations, 5 reviews

h-index: 16

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Drug delivery systems

Polymer science

Supramolecular chemistry

Surfactants

1 citation

Kuznetsov Denis

PhD in Chemistry

46 publications, 580 citations

h-index: 14

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

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GOST |

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Tatarinov D. et al. Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation // Tetrahedron. 2016. Vol. 72. No. 51. pp. 8493-8501.

GOST all authors (up to 50) Copy

Tatarinov D., Kuznetsov D. M., Voloshina A. D., Lyubina A. P., Strobykina A. S., Mukhitova F. K., Polyancev F. M., Mironov V. L. Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation // Tetrahedron. 2016. Vol. 72. No. 51. pp. 8493-8501.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2016.11.023

UR - https://doi.org/10.1016/j.tet.2016.11.023

TI - Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation

T2 - Tetrahedron

AU - Tatarinov, Dmitry

AU - Kuznetsov, Denis M

AU - Voloshina, A. D.

AU - Lyubina, Anna P

AU - Strobykina, Anastasiya S

AU - Mukhitova, Fahima K

AU - Polyancev, Fedor M

AU - Mironov, Valery L.

PY - 2016

DA - 2016/12/01

PB - Elsevier

SP - 8493-8501

IS - 51

VL - 72

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2016_Tatarinov,

author = {Dmitry Tatarinov and Denis M Kuznetsov and A. D. Voloshina and Anna P Lyubina and Anastasiya S Strobykina and Fahima K Mukhitova and Fedor M Polyancev and Valery L. Mironov},

title = {Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation},

journal = {Tetrahedron},

year = {2016},

volume = {72},

publisher = {Elsevier},

month = {dec},

url = {https://doi.org/10.1016/j.tet.2016.11.023},

number = {51},

pages = {8493--8501},

doi = {10.1016/j.tet.2016.11.023}

}

MLA

Cite this

MLA Copy

Tatarinov, Dmitry, et al. “Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation.” Tetrahedron, vol. 72, no. 51, Dec. 2016, pp. 8493-8501. https://doi.org/10.1016/j.tet.2016.11.023.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)

Profiles

Denis Mihaylovich Kuznetsov