Tetrahedron

, volume 74 , issue 15 , pages 1838-1849

Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation

Dmitry S. Ryabukhin ¹

Anna D Lisakova ²

Anna S. Zalivatskaya ³

Irina A Boyarskaya ³

G. L. Starova ³

Rostislav E Trifonov ^{4, 5}

Vladimir A Ostrovskii ²

Aleksander V Vasilyev ⁴

Hide authors affiliations Show authors affiliations: 5 affiliations

Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, 194021, Russia |

Saint Petersburg State Institute of Technology (Technical University), Moskovsky pr. 26, Saint Petersburg 190013, Russia |

Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab., 7/9, Saint Petersburg 199034, Russia |

⁴

Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab., 7/9, Saint Petersburg, 199034, Russia |

⁵

Saint Petersburg State Institute of Technology (Technical University), Moskovsky Pr., 26, Saint Petersburg, 190013, Russia |

Publication type: Journal Article

Publication date: 2018-04-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2018.02.050

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Organic Chemistry

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Biochemistry

Abstract

Reaction of 5-arylethynyl-2-methyl-2H-tetrazoles (acetylene tetrazoles) with arenes under the action of Bronsted superacid CF3SO3H or acidic zeolite HUSY CBV-720 gives rise to E-/Z-5-(2,2-diarylethenyl)-2-methyl-2H-tetrazoles, as products of hydroarylation of acetylene bond, in yields up to 98% with predominant formation of E-isomers. Cationic intermediates of these reactions have been studied theoretically by DFT calculations. Addition of CF3SO3H to the triple bond of acetylene tetrazoles leads to the corresponding E-/Z-vinyl triflates in high yields. Hydration of triple bond in these tetrazoles in H2SO4 results in the formation of 5-(2-aryl-2-oxoethyl)-2-methyl-2H-tetrazoles. Tandem hydroarylation-ionic hydrogenation of acetylene tetrazoles in the systems acid(CF3SO3H or AlCl3)-arene-cyclohexane affords 5-(2,2-diarylethyl)-2-methyl-2H-tetrazoles.

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Aksenov Aleksandr

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DSc in Chemistry, professor

243 publications, 2 163 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 707 citations

h-index: 30

Ural Federal University

1 citation

Ivleva Elena

67 publications, 465 citations

h-index: 12

Samara State Technical University

Research interests

Organic Chemistry

Organic synthesis

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Ryabukhin D. S. et al. Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation // Tetrahedron. 2018. Vol. 74. No. 15. pp. 1838-1849.

GOST all authors (up to 50) Copy

Ryabukhin D. S., Lisakova A. D., Zalivatskaya A. S., Boyarskaya I. A., Starova G. L., Trifonov R. E., Ostrovskii V. A., Vasilyev A. V. Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation // Tetrahedron. 2018. Vol. 74. No. 15. pp. 1838-1849.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2018.02.050

UR - https://doi.org/10.1016/j.tet.2018.02.050

TI - Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation

T2 - Tetrahedron

AU - Ryabukhin, Dmitry S.

AU - Lisakova, Anna D

AU - Zalivatskaya, Anna S.

AU - Boyarskaya, Irina A

AU - Starova, G. L.

AU - Trifonov, Rostislav E

AU - Ostrovskii, Vladimir A

AU - Vasilyev, Aleksander V

PY - 2018

DA - 2018/04/01

PB - Elsevier

SP - 1838-1849

IS - 15

VL - 74

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2018_Ryabukhin,

author = {Dmitry S. Ryabukhin and Anna D Lisakova and Anna S. Zalivatskaya and Irina A Boyarskaya and G. L. Starova and Rostislav E Trifonov and Vladimir A Ostrovskii and Aleksander V Vasilyev},

title = {Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation},

journal = {Tetrahedron},

year = {2018},

volume = {74},

publisher = {Elsevier},

month = {apr},

url = {https://doi.org/10.1016/j.tet.2018.02.050},

number = {15},

pages = {1838--1849},

doi = {10.1016/j.tet.2018.02.050}

}

MLA

Cite this

MLA Copy

Ryabukhin, Dmitry S., et al. “Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation.” Tetrahedron, vol. 74, no. 15, Apr. 2018, pp. 1838-1849. https://doi.org/10.1016/j.tet.2018.02.050.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)

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