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Triazoles and Tetrazoles: Current Status and Perspective

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 March 2024) | Viewed by 2745

Special Issue Editor


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Guest Editor
Department of Organic Chemistry, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia
Interests: synthesis; properties; reactivity and low tonnage technology for the production of nitrogen-rich heterocyclic compounds as components of energetic materials; modern polymers; catalysts of automatics oligonucleotides synthesis; active ingredients of medicinal

Special Issue Information

Dear Colleagues,

This Special Issue will focus on 1,2,3-triazole (Hans von Pechmann (1888)), 1,2,4-triazole and tetrazole (Johan A. Bladin (1885)) derivatives as unique members of the azole series.

Derivatives of tri- and tetrazole present significant interest as nitrogen-rich components in energetic systems and materials, in modern polymers, as catalysts of automatics oligonucleotides synthesis, active ingredients in modern medicinal remedies for the curing of bacterial and viral infections, arterial hypertension, deceases in the central nervous system, allergies, etc.

It is appropriate to note that 1,2,3-triazoles and tetrazoles are the main objects of the click-chemistry and bioorthogonal chemistry concepts of Carolyn R. Bertozzi, Morten Meldal and K. Barry Sharpless, who were awarded the Nobel Prize for Chemistry in 2022.

The editors are interested in attracting authors of reviews and experimental articles, the topics of which cover the pressing problems of methods of ring formation and ring degradation, ring functionalization with the participation of exo- and endocyclic atoms, reactivity, specific features of physicochemical properties with some thermodynamically properties among them, and the nature of their biological activity. Knowledge of these factors determines the use of 1,2,3-triazoles, 1,2,4-triazoles and tetrazoles in medicine and practice. It is very important not only to identify the current status of fundamental and applied research, but also to focus the attention of a wide range of readers on the most promising areas that open new horizons in the chemistry of nitrogen-rich heterocyclic compounds, that is, on 1,2,3-triazoles, 1,2,4-triazoles, and tetrazoles.

Dr. Vladimir А. Ostrovskii
Guest Editor

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Keywords

  • 1,2,3-triazoles
  • 1,2,4-triazoles
  • tetrazoles
  • synthesis
  • decomposition
  • structure
  • properties
  • reactivity
  • application

Published Papers (2 papers)

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Research

23 pages, 7944 KiB  
Article
Novel 1,2,4-Triazole- and Tetrazole-Containing 4H-Thiopyrano[2,3-b]quinolines: Synthesis Based on the Thio-Michael/aza-Morita–Baylis–Hillman Tandem Reaction and Investigation of Antiviral Activity
by Andrey V. Khramchikhin, Mariya A. Skryl’nikova, Maxim A. Gureev, Vladimir V. Zarubaev, Iana L. Esaulkova, Polina A. Ilyina, Oussama Abdelhamid Mammeri, Dar’ya V. Spiridonova, Yuri B. Porozov and Vladimir A. Ostrovskii
Molecules 2023, 28(21), 7427; https://doi.org/10.3390/molecules28217427 - 04 Nov 2023
Cited by 1 | Viewed by 912
Abstract
A novel method for synthesizing 1,2,4-triazole- and tetrazole-containing 4H-thiopyrano[2,3-b]quinolines using a new combination of the thio-Michael and aza-Morita–Baylis–Hillman reactions was developed. Target compounds were evaluated for their cytotoxicities and antiviral activities against influenza A/Puerto Rico/8/34 virus in MDCK cells. [...] Read more.
A novel method for synthesizing 1,2,4-triazole- and tetrazole-containing 4H-thiopyrano[2,3-b]quinolines using a new combination of the thio-Michael and aza-Morita–Baylis–Hillman reactions was developed. Target compounds were evaluated for their cytotoxicities and antiviral activities against influenza A/Puerto Rico/8/34 virus in MDCK cells. The compounds showed low toxicity and some exhibited moderate antiviral activity. Molecular docking identified the M2 channel and polymerase basic protein 2 as potential targets. We observed that the antiviral activity of thiopyrano[2,3-b]quinolines is notably affected by both the nature and position of the substituent within the tetrazole ring, as well as the substituent within the benzene moiety of quinoline. These findings contribute to the further search for new antiviral agents against influenza A viruses among derivatives of thiopyrano[2,3-b]quinoline. Full article
(This article belongs to the Special Issue Triazoles and Tetrazoles: Current Status and Perspective)
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14 pages, 5560 KiB  
Article
Differentiation between Isomeric 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles by ESI-HRMS and IR Ion Spectroscopy
by Dmitrii M. Mazur, Elettra L. Piacentino, Giel Berden, Jos. Oomens, Victor Ryzhov, Vasiliy A. Bakulev and Albert T. Lebedev
Molecules 2023, 28(3), 977; https://doi.org/10.3390/molecules28030977 - 18 Jan 2023
Viewed by 1427
Abstract
A large variety of 1,2,3-thiadiazoles and 1,2,3-triazoles are used extensively in modern pure and applied organic chemistry as important structural blocks of numerous valuable products. Creation of new methods of synthesis of these isomeric compounds requires the development of reliable analytical tools to [...] Read more.
A large variety of 1,2,3-thiadiazoles and 1,2,3-triazoles are used extensively in modern pure and applied organic chemistry as important structural blocks of numerous valuable products. Creation of new methods of synthesis of these isomeric compounds requires the development of reliable analytical tools to reveal the structural characteristics of these novel compounds, which are able to distinguish between isomers. Mass spectrometry (MS) is a clear choice for this task due to its selectivity, sensitivity, informational capacity, and reliability. Here, the application of electrospray ionization (ESI) with ion detection in positive and negative modes was demonstrated to be useful in structural studies. Additionally, interconversion of isomeric 4,5-functionalized 1,2,3-triazoles and 1,2,3-thiadiazoles was demonstrated. Application of accurate mass measurements and tandem mass spectrometry in MS2 and MS3 modes indicated the occurrence of gas-phase rearrangement of 1,2,3-triazoles into 1,2,3-thiadiazoles under (+)ESI-MS/MS conditions, independent of the nature of substituents, in line with the reaction in the condensed phase. Infrared multiple photon dissociation (IRMPD) spectroscopy enabled the establishment of structures of some of the most crucial common fragment ions, including [M+H-N2]+ and [M+H-N2-RSO2]+ species. The (−)ESI-MS/MS experiments were significantly more informative for the sulfonyl alkyl derivatives compared to the sulfonyl aryl ones. However, there was insufficient evidence to confirm the solution-phase transformation of 1,2,3-thiadiazoles into the corresponding 1,2,3-triazoles. Full article
(This article belongs to the Special Issue Triazoles and Tetrazoles: Current Status and Perspective)
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