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Heterocyclic Chemistry in Europe
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Heterocyclic Chemistry in Europe

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

Deadline for manuscript submissions: 31 March 2025 | Viewed by 6983

Special Issue Editor

Dr. Gilbert Kirsch

E-Mail Website
Guest Editor
Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), Université de Lorraine, 57078 Metz, France
Interests: organic synthesis (Vilsmeier-Haack, Fischer indole,....); heterocycles; thiophenes and benzothiophenes; selenophenes and benzoselenophenes; coumarines; flavanoids; indoles; carbazoles
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Heterocycles are defined as “Carbocycles containing at least one heteroatom”. With this definition, it is easy to understand that examples of this type will be numerous. For example, for those who are familiar with the Chemical Abstracts in the paper version, they will remember that, in the Heterocycles section, the first to appear were epoxides. In Europe and all over the world, heterocycles are certainly the most studied organic compounds. Aromatic or non-aromatic, benzocondensed or not, monoheteroatomic or polyheteroatomic, the possible variety of compounds were studied to prepare a new synthesis, to develop compounds for specific properties in medicinal chemistry or material science. Additionally, many natural compounds are part of the different classes. This Special Issue will focus on the synthesis of heterocyclic compounds of all types. Heterocycles used as intermediates for the construction of more complex molecules (as developed by Boger, Padwa…) are welcome in this Special Issue.

Dr. Gilbert Kirsch
Guest Editor

Manuscript Submission Information

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Keywords

  • non-aromatic heterocycles
  • aromatic heterocycles
  • benzo-condensed heterocycles
  • mesoionic heterocycles
  • natural heterocycles
  • synthesis
  • reactivity

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Published Papers (5 papers)

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Research

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14 pages, 2300 KiB  
Article
Palladium-Catalyzed Arylations towards 3,6-Diaryl-1,3a,6a-triazapentalenes and Evaluation of Their Fluorescence Properties
by Yingchun Wang, Tomas Opsomer, Flip de Jong, Davy Verhaeghe, Maarten Mulier, Luc Van Meervelt, Mark Van der Auweraer and Wim Dehaen
Molecules 2024, 29(10), 2229; https://doi.org/10.3390/molecules29102229 - 9 May 2024
Viewed by 995
Abstract
Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate (TAP1) shows interesting properties as a small molecule fluorophore. In the search for post-functionalization methods, palladium-catalyzed arylation reactions were demonstrated. Direct CH arylation reactions of TAP1 with various aryl halides resulted in 3,6-diaryltriazapentalenes TAP4, although mostly in poor [...] Read more.
Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate (TAP1) shows interesting properties as a small molecule fluorophore. In the search for post-functionalization methods, palladium-catalyzed arylation reactions were demonstrated. Direct CH arylation reactions of TAP1 with various aryl halides resulted in 3,6-diaryltriazapentalenes TAP4, although mostly in poor yields. Bromination of TAP1 followed by Suzuki coupling, on the other hand, requires a more delicate procedure, but gave arylated products with the same regiochemistry (TAP4) in moderate to good yields. The structure of 6-phenyltriazapentalene TAP4a was confirmed by crystallographic analysis. In addition, the effect of the C6 arylation on the fluorescent properties of 3-aryl-1,3a,6a-triazapentalenes was studied in dichloromethane at room temperature and in 2-methyltetrahydrofuran at 77 K, while the photophysical properties of two saponified derivatives were measured in acetonitrile. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry in Europe)
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17 pages, 1695 KiB  
Article
Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents
by Artyom E. Paromov
Molecules 2023, 28(22), 7648; https://doi.org/10.3390/molecules28227648 - 17 Nov 2023
Viewed by 1483
Abstract
The synthesis of substituted 2,4,6,8,10,12-hexaazaisowurtzitane via direct condensation is challenging. The selection of starting ammonia derivatives is very limited. The important step in developing alternative synthetic routes to these compounds is to investigate their formation process in detail. Here, we examined an acid-catalyzed [...] Read more.
The synthesis of substituted 2,4,6,8,10,12-hexaazaisowurtzitane via direct condensation is challenging. The selection of starting ammonia derivatives is very limited. The important step in developing alternative synthetic routes to these compounds is to investigate their formation process in detail. Here, we examined an acid-catalyzed condensation between benzyl carbamate and glyoxal in a ratio of 2:1 in a range of polar protic and aprotic solvents, and discovered a new process occurring during the cascade condensation of glyoxal with ammonia derivatives as well as discovered several processes hindering the formation of caged compounds. More specifically, a cyclic compound, N,N′-bis(carbobenzoxy)-3,6-diamino-1,4-dioxane-2,5-diol, was found to form at the early stage of condensation under low acidity conditions. The formation of this compound is governed by an easier condensation of alcohol groups compared to the amide ones. The condensation intermediates, N,N′-bis(carbobenzoxy)ethan-1,2-diol, N,N′,N″-tris(carbobenzoxy)ethanol, and N,N′,N″,N‴-tetrakis(carbobenzoxy)ethan, were obtained at a higher acidity. A range of solvents were identified: those that react with benzyl carbamate, those that promote the progress of side processes, and those that promote precipitation of condensation intermediates. A few byproducts were isolated and identified. It was found that DMSO exhibits a strong deactivating ability, while CH3CN exhibits a strong activating ability towards the acid-catalyzed condensation process of benzyl carbamate with glyoxal. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry in Europe)
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12 pages, 3451 KiB  
Article
Synthesis of Functionalized 3H-pyrrolo-[1,2,3-de] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes
by Antonia Iazzetti, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Alessio Sferrazza and Karim Ullah
Molecules 2023, 28(15), 5831; https://doi.org/10.3390/molecules28155831 - 2 Aug 2023
Cited by 1 | Viewed by 1118
Abstract
A gold-catalyzed protocol to obtain functionalized 3H-pyrrolo [1,2,3-de] quinoxalines from suitable substituted N-alkynyl indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the [...] Read more.
A gold-catalyzed protocol to obtain functionalized 3H-pyrrolo [1,2,3-de] quinoxalines from suitable substituted N-alkynyl indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the isolation of title compounds with yields from good to high. A reaction mechanism has been proposed, and theoretical calculations have been provided to rationalize the final step of the hypothesized reaction mechanism. As quinoxaline-containing polycyclic compounds, this class of molecules may represent a valuable template in medicinal chemistry and material science. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry in Europe)
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Review

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26 pages, 4587 KiB  
Review
Formation and Reactions of Brønsted and Lewis Acid Adducts with Electron-Rich Heteroaromatic Compounds
by Horst Hartmann and Jürgen Liebscher
Molecules 2024, 29(13), 3151; https://doi.org/10.3390/molecules29133151 - 2 Jul 2024
Viewed by 1043
Abstract
Electron-rich heteroaromatics, such as furan, thiophene and pyrrole, as well as their benzo-condensed derivatives, are of great interest as components of natural products and as starting substances for various products including high-tech materials. Although their reactions with Brønsted and Lewis acids play important [...] Read more.
Electron-rich heteroaromatics, such as furan, thiophene and pyrrole, as well as their benzo-condensed derivatives, are of great interest as components of natural products and as starting substances for various products including high-tech materials. Although their reactions with Brønsted and Lewis acids play important roles, in particular as the primary step of various transformations, they are often disregarded and mechanistically not understood. The present publication gives a first overview about this chemistry focusing on the parent compounds. It comprises reactions with strong Brønsted acids forming adducts that can undergo intramolecular proton and/or substituent transfer reactions, ring openings or ring transformations into other heterocycles, depending on their structure. Interactions with weak Brønsted acids usually initiate oligomerizations/polymerizations. A similar behaviour is observed in reactions of these heteroaromatics with Lewis acids. Special effects are achieved when the Lewis acids are activated through primary protonation. Deuterated Brønsted acids allow straight forward deuteration of electron-rich heteroaromatics. Mercury salts as extremely weak Lewis acids cause direct metalation in a straight forward way replacing ring H-atoms yielding organomercury heterocycles. This review will provide comprehensive information about the chemistry of adducts of such heterocycles with Brønsted and Lewis acids enabling chemists to understand the mechanisms and the potential of this field and to apply the findings in future syntheses. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry in Europe)
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26 pages, 2994 KiB  
Review
Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications
by Giorgio Volpi, Enzo Laurenti and Roberto Rabezzana
Molecules 2024, 29(11), 2668; https://doi.org/10.3390/molecules29112668 - 5 Jun 2024
Cited by 1 | Viewed by 1643
Abstract
In recent years, there has been increasing attention focused on various products belonging to the imidazopyridine family; this class of heterocyclic compounds shows unique chemical structure, versatile optical properties, and diverse biological attributes. The broad family of imidazopyridines encompasses different heterocycles, each with [...] Read more.
In recent years, there has been increasing attention focused on various products belonging to the imidazopyridine family; this class of heterocyclic compounds shows unique chemical structure, versatile optical properties, and diverse biological attributes. The broad family of imidazopyridines encompasses different heterocycles, each with its own specific properties and distinct characteristics, making all of them promising for various application fields. In general, this useful category of aromatic heterocycles holds significant promise across various research domains, spanning from material science to pharmaceuticals. The various cores belonging to the imidazopyridine family exhibit unique properties, such as serving as emitters in imaging, ligands for transition metals, showing reversible electrochemical properties, and demonstrating biological activity. Recently, numerous noteworthy advancements have emerged in different technological fields, including optoelectronic devices, sensors, energy conversion, medical applications, and shining emitters for imaging and microscopy. This review intends to provide a state-of-the-art overview of this framework from 1955 to the present day, unveiling different aspects of various applications. This extensive literature survey may guide chemists and researchers in the quest for novel imidazopyridine compounds with enhanced properties and efficiency in different uses. Full article
(This article belongs to the Special Issue Heterocyclic Chemistry in Europe)
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