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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 May 2024 | Viewed by 2038

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

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 2700 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

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

Published Papers (2 papers)

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Research

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 890
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 - 02 Aug 2023
Cited by 1 | Viewed by 747
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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