Tetrahedron, volume 103, pages 132563

Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles

Titenkova Kseniia Yu ^{1, 2}

Fershtat Leonid L. ²

Larin Alexander A ²

Shaferov Alexander V ²

Kulikov Alexander S.

Epishina Margarita A. ²

Kulikov Alexander ²

Ananyev Ivan V ^{3, 4}

Hide authors affiliations Show authors affiliations: 4 affiliations

Department of Chemistry, Moscow State University, 119991, Leninskie Gory 1-3, Moscow, Russia |

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prosp., 47, Moscow, Russia |

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str. 28, Moscow, Russia. |

⁴

Plekhanov Russian University of Economics 117997 Stremyanny per. 36 Moscow Russia |

Publication type: Journal Article

Publication date: 2022-01-01

Elsevier

Journal: Tetrahedron

Quartile SCImago

Quartile WOS

Impact factor: 2.1

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2021.132563

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

A general method for the synthesis of a series of previously unknown N -(heteroaryl)- and N -(aryl)aminotetrazoles through the tandem electrocyclization/hydrolysis of azidohydrazones was accomplished. The described protocol was suitable for a wide array of the target N -substituted aminotetrazoles which were prepared in good to high yields under smooth reaction conditions. Importantly, the presented approach is considered as a direct route to 1,2,5-oxadiazole-substituted aminotetrazole derivatives in good and high yields and may be realized on a gram scale. Therefore, facile synthesis of N -(heteroaryl)- and N -(aryl)aminotetrazoles unveils novel opportunities to study application prospectives of these compounds as functional materials or drug candidates. • A general method for the synthesis of N -aminotetrazoles was developed. • The reaction has a wide substrate scope and proceeds under mild conditions. • No aminating reagents are required.

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Molecules	Molecules, 1, 33.33% Molecules 1 publication, 33.33%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 33.33% Chemistry - A European Journal 1 publication, 33.33%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 1, 33.33% Progress in Heterocyclic Chemistry 1 publication, 33.33%
	1

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Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 33.33% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 33.33%
Wiley	Wiley, 1, 33.33% Wiley 1 publication, 33.33%
Elsevier	Elsevier, 1, 33.33% Elsevier 1 publication, 33.33%
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Titenkova K. Yu. et al. Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles // Tetrahedron. 2022. Vol. 103. p. 132563.

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Titenkova K. Yu., Shaferov A. V., Larin A. A., Epishina M. A., Kulikov A. S., Fershtat L. L., Kulikov A., Ananyev I. V. Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles // Tetrahedron. 2022. Vol. 103. p. 132563.

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2021.132563

UR - https://doi.org/10.1016%2Fj.tet.2021.132563

TI - Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles

T2 - Tetrahedron

AU - Titenkova, Kseniia Yu

AU - Shaferov, Alexander V

AU - Larin, Alexander A

AU - Epishina, Margarita A.

AU - Kulikov, Alexander S.

AU - Fershtat, Leonid L.

AU - Kulikov, Alexander

AU - Ananyev, Ivan V

PY - 2022

DA - 2022/01/01 00:00:00

PB - Elsevier

SP - 132563

VL - 103

SN - 0040-4020

SN - 1464-5416

ER -

BibTex

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@article{2022_Titenkova,

author = {Kseniia Yu Titenkova and Alexander V Shaferov and Alexander A Larin and Margarita A. Epishina and Alexander S. Kulikov and Leonid L. Fershtat and Alexander Kulikov and Ivan V Ananyev},

title = {Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles},

journal = {Tetrahedron},

year = {2022},

volume = {103},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016%2Fj.tet.2021.132563},

pages = {132563},

doi = {10.1016/j.tet.2021.132563}

}

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Publisher

Elsevier

Journal

Tetrahedron

Quartile SCImago

Quartile WOS

Impact factor

2.1

ISSN

00404020 (Print)
14645416 (Electronic)

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