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Special Issue "Novelties in N-Heterocycles Chemistry: From Synthesis to Application"

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

Deadline for manuscript submissions: 30 September 2022 | Viewed by 1951

Special Issue Editors

Dr. Ekaterina A. Knyazeva
E-Mail Website
Guest Editor
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Interests: chalcogen-nitrogen heterocycles; synthesis of heterocycles; organic sensitizers; organic solar cells fabrication; organic functional materials; photovoltaic efficiency
Prof. Dr. Leonid L. Fershtat
E-Mail Website
Guest Editor
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Interests: nitrogen heterocycles; nitrogen-oxygen molecular systems; energetic materials; nitric oxide donors; pharmacologically active heterocycles; ionic liquids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

N-Heterocycles are ubiquitous not only in organic chemistry, but also in medicinal chemistry, materials science, agrochemistry, and other related fields. It is rare to find a scientific group whose work or part of it would not directly or indirectly come into contact with nitrogen-containing heterocycles. Therefore, the development of the chemistry of nitrogenous heterocycles is of paramount importance not only for researchers working directly in this field, but also for scientists in related branches of science.

The purpose of this Special Issue is to demonstrate the latest synthetic methods, rich chemistry and the broadest possibilities of using nitrogen-containing heterocycles.

Dr. Ekaterina A. Knyazeva
Prof. Dr. Leonid L. Fershtat
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2300 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • nitrogen heterocycles
  • cyclization
  • cycloaddition
  • C-H functionalization
  • pharmacologically active heterocycles
  • organic functional materials

Published Papers (3 papers)

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Research

Article
Anions Containing Tripoid Conjugated N4 System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability
Molecules 2022, 27(19), 6287; https://doi.org/10.3390/molecules27196287 - 23 Sep 2022
Viewed by 165
Abstract
A strategy for the synthesis of 5-((2-cyanoethyl)-X-amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides (X = H; CH2CH2CN; NO2 (4a); CN (4b); CO2Et (4c)) starting from 3-amino-4-azido-1,2,5-oxadiazole was developed. The key step in this strategy [...] Read more.
A strategy for the synthesis of 5-((2-cyanoethyl)-X-amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides (X = H; CH2CH2CN; NO2 (4a); CN (4b); CO2Et (4c)) starting from 3-amino-4-azido-1,2,5-oxadiazole was developed. The key step in this strategy is the intramolecular thermolytic cyclization of the azido group and the bis(2-cyanoethyl)triazene group. Removal of the 2-cyanoethyl protecting group from amides 4ac gave potassium salt of the corresponding nitramide and sodium salts of cyano- and ethoxycarbonylamide. The structure and thermal stability of the synthesized compounds were studied experimentally using multinuclear NMR spectroscopy, X-ray crystallography, thermogravimetry, and differential scanning calorimetry. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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Article
Bicyclic Isoxazoline Derivatives: Synthesis and Evaluation of Biological Activity
Molecules 2022, 27(11), 3546; https://doi.org/10.3390/molecules27113546 - 31 May 2022
Viewed by 528
Abstract
The application of non-planar scaffolds in drug design allows for the enlargement of the chemical space, and for the construction of molecules that have more effective target–ligand interactions or are less prone to the development of resistance. Among the works of the last [...] Read more.
The application of non-planar scaffolds in drug design allows for the enlargement of the chemical space, and for the construction of molecules that have more effective target–ligand interactions or are less prone to the development of resistance. Among the works of the last decade, a literature search revealed spirothiazamenthane, which has served as a lead in the development of derivatives active against resistant viral strains. In this work, we studied the novel molecular scaffold, which resembles spirothiazamenthane, but combines isoxazoline as a heterocycle and cyclooctane ring as a hydrophobic part of the structure. The synthesis of new 3-nitro- and 3-aminoisoxazolines containing spiro-fused or 1,2-annelated cyclooctane fragments was achieved by employing 1,3-dipolar cycloaddition of 3-nitro-4,5-dihydroisoxazol-4-ol 2-oxide or tetranitromethane-derived alkyl nitronates with non-activated alkenes. A series of spiro-sulfonamides was obtained by the reaction of 3-aminoisoxazoline containing a spiro-fused cyclooctane residue with sulfonyl chlorides. Preliminary screening of the compounds for antiviral, antibacterial, antifungal and antiproliferative properties in vitro revealed 1-oxa-2-azaspiro[4.7]dodec-2-en-3-amine and 3a,4,5,6,7,8,9,9a-octahydrocycloocta[d]isoxazol-3-amine with activity against the influenza A/Puerto Rico/8/34 (H1N1) virus in the submicromolar range, and high values of selectivity index. Further study of the mechanism of the antiviral action of these compounds, and the synthesis of their analogues, is likely to identify new agents against resistant viral strains. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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Article
Revisiting the Synthesis of Functionally Substituted 1,4-Dihydrobenzo[e][1,2,4]triazines
Molecules 2022, 27(8), 2575; https://doi.org/10.3390/molecules27082575 - 15 Apr 2022
Viewed by 626
Abstract
A series of novel 1,4-dihydrobenzo[1,2,4][e]triazines bearing an acetyl or ester moiety as a functional group at the C(3) atom of the 1,2,4-triazine ring were synthesized. The synthetic protocol is based on an oxidative cyclization of functionally substituted amidrazones in the presence [...] Read more.
A series of novel 1,4-dihydrobenzo[1,2,4][e]triazines bearing an acetyl or ester moiety as a functional group at the C(3) atom of the 1,2,4-triazine ring were synthesized. The synthetic protocol is based on an oxidative cyclization of functionally substituted amidrazones in the presence of DBU and Pd/C. It was found that the developed approach is suitable for the preparation of 1,4-dihydrobenzo[e][1,2,4]triazines, but the corresponding Blatter radicals were isolated only in few cases. In addition, a previously unknown dihydrobenzo[e][1,2,4]triazolo[3,4-c][1,2,4]triazine tricyclic open-shell derivative was prepared. Studies of thermal behavior of the synthesized 1,4-dihydrobenzo[1,2,4][e]triazines revealed their high thermal stability (up to 240–250 °C), which enables their application potential as components of functional organic materials. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: The investigation of palladium-catalyzed C-H activation reactions of benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole and 4,8-dibromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole)
Authors: Timofey N. Chmovzh; Timofey A. Kudryashev; Daria A. Alekhina; Konstantin P.Trainov; Ludmila V. Mikhalchenko; Oleg A. Rakitin
Affiliation: N. D. Zelinsky Institute of Organic Chemistry RAS, Moscow, Russia
Abstract: The investigation of palladium-catalyzed C-H activation reactions of benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole is reported. For the first time, palladium catalysed cross-coupling reactions of a hetero and arylated derivatives was found to be a powerful tool for the selective formation of various mono- and diarylated derivatives of strongly electron accepting heterocycles. C-H Activation coupling can be successfully employed for the preparation of mono-arylated and bis-derivatives. Also, C-H activation of aryl derivatives was studied for 4,8-dibromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole). Important physico-chemical properties such as absorption spectra (UV), and luminescence spectra, and cyclic voltammograms were measured and analysed for diarylated derivatives.

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