Recent advances in the denitrogenative annulation reactions of 1,2,3-thiadiazoles

Marina A. Tokareva; Tatiana V. Glukhareva; Sinead T. Keaveney

doi:10.1002/cctc.202301488

Recent advances in the denitrogenative annulation reactions of 1,2,3-thiadiazoles

Marina A. Tokareva, Tatiana V. Glukhareva, Sinead T. Keaveney^*

^*Corresponding author for this work

School of Natural Sciences

Research output: Contribution to journal › Review article › peer-review

9 Citations (Scopus)

189 Downloads (Pure)

Abstract

1,2,3-Thiadiazoles exhibit versatile reactivity due to their ability to undergo ring cleavage, forming α-diazothione species through a Dimroth-type equilibrium. Denitrogenation of the α-diazothione, induced by high temperature, irradiation, or strong bases, allows generation of a wide range of reactive intermediates. Since 2016, the transition-metal-catalyzed denitrogenative transannulation of 1,2,3-thiadiazoles has garnered significant attention as a promising approach to constructing diverse heterocyclic scaffolds. This review focuses on the denitrogenative reactions of 1,2,3-thiadiazoles, particularly highlighting the novel rhodium-catalyzed denitrogenative transannulation transformations along with their mechanisms.

Original language	English
Article number	e202301488
Pages (from-to)	1-17
Number of pages	17
Journal	ChemCatChem
Volume	16
Issue number	14
Early online date	22 Jan 2024
DOIs	https://doi.org/10.1002/cctc.202301488
Publication status	Published - 22 Jul 2024

Bibliographical note

Copyright the Author(s) 2024. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

1,2,3-thiadiazole
catalysis
denitrogenation
heterocycles
rhodium

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10.1002/cctc.202301488

Publisher version (open access)Final published version, 23.1 MBLicence: CC BY

Cite this

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title = "Recent advances in the denitrogenative annulation reactions of 1,2,3-thiadiazoles",

abstract = "1,2,3-Thiadiazoles exhibit versatile reactivity due to their ability to undergo ring cleavage, forming α-diazothione species through a Dimroth-type equilibrium. Denitrogenation of the α-diazothione, induced by high temperature, irradiation, or strong bases, allows generation of a wide range of reactive intermediates. Since 2016, the transition-metal-catalyzed denitrogenative transannulation of 1,2,3-thiadiazoles has garnered significant attention as a promising approach to constructing diverse heterocyclic scaffolds. This review focuses on the denitrogenative reactions of 1,2,3-thiadiazoles, particularly highlighting the novel rhodium-catalyzed denitrogenative transannulation transformations along with their mechanisms.",

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AU - Glukhareva, Tatiana V.

AU - Keaveney, Sinead T.

N1 - Copyright the Author(s) 2024. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

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Y1 - 2024/7/22

N2 - 1,2,3-Thiadiazoles exhibit versatile reactivity due to their ability to undergo ring cleavage, forming α-diazothione species through a Dimroth-type equilibrium. Denitrogenation of the α-diazothione, induced by high temperature, irradiation, or strong bases, allows generation of a wide range of reactive intermediates. Since 2016, the transition-metal-catalyzed denitrogenative transannulation of 1,2,3-thiadiazoles has garnered significant attention as a promising approach to constructing diverse heterocyclic scaffolds. This review focuses on the denitrogenative reactions of 1,2,3-thiadiazoles, particularly highlighting the novel rhodium-catalyzed denitrogenative transannulation transformations along with their mechanisms.

AB - 1,2,3-Thiadiazoles exhibit versatile reactivity due to their ability to undergo ring cleavage, forming α-diazothione species through a Dimroth-type equilibrium. Denitrogenation of the α-diazothione, induced by high temperature, irradiation, or strong bases, allows generation of a wide range of reactive intermediates. Since 2016, the transition-metal-catalyzed denitrogenative transannulation of 1,2,3-thiadiazoles has garnered significant attention as a promising approach to constructing diverse heterocyclic scaffolds. This review focuses on the denitrogenative reactions of 1,2,3-thiadiazoles, particularly highlighting the novel rhodium-catalyzed denitrogenative transannulation transformations along with their mechanisms.

KW - 1,2,3-thiadiazole

KW - catalysis

KW - denitrogenation

KW - heterocycles

KW - rhodium

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JF - ChemCatChem

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ER -

Recent advances in the denitrogenative annulation reactions of 1,2,3-thiadiazoles

Abstract

Bibliographical note

Keywords

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