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Polycyclic(hetero)aromatic Compounds

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

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 4913

Special Issue Editor

Dipartimento di Scienze Farmaceutiche, Università di Perugia, 06123 Perugia, Italy
Interests: multicomponent reactions for low environmental impact synthesis; organoselenium chemistry; stereoselective synthesis of heterocyclic compounds; Diels-Alder reactions for the synthesis of (hetero)biaryls and stilbenes; green synthetic methodology in organic chemistry
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Special Issue Information

Dear Colleagues,

Polycyclic(hetero)aromatic compounds are an important class of organic molecules that have found applications as ligands for metals, in pharmaceutical and material sciences. Consequently, the development of new and more efficient synthetic methods for this class of compounds is important to organic chemists. Inter- and intramolecular cycloadditions, cyclization, and transition-metal catalyzed cross-coupling procedures are important and widely used methods for the synthesis of polycyclic(hetero)aromatic compounds in single or multistep process.

Prof. Dr. Andrea Temperini
Guest Editor

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Keywords

  • polycyclic
  • (hetero)aromatic
  • bioactive compounds
  • organic synthesis
  • cyclization

Published Papers (2 papers)

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Research

18 pages, 11780 KiB  
Article
Solvent Moisture-Controlled Self-Assembly of Fused Benzoimidazopyrrolopyrazines with Different Ring’s Interposition
by Svetlana V. Martynovskaya, Arsalan B. Budaev, Igor A. Ushakov, Tatyana N. Borodina and Andrey V. Ivanov
Molecules 2022, 27(8), 2460; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27082460 - 11 Apr 2022
Cited by 1 | Viewed by 1267
Abstract
This article shows that two extremely important families of fused heterocyclic assemblies, namely 6-methylbenzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazine and 5a-methyl-5a,6-dihydro-5H,12H-benzo[4,5]imidazo[1,2-a]pyrrolo[1,2-d]pyrazine, can be synthesized from only two available building blocks (N-allenylpyrrole-2-carbaldehyde and o-phenylenediamine) [...] Read more.
This article shows that two extremely important families of fused heterocyclic assemblies, namely 6-methylbenzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazine and 5a-methyl-5a,6-dihydro-5H,12H-benzo[4,5]imidazo[1,2-a]pyrrolo[1,2-d]pyrazine, can be synthesized from only two available building blocks (N-allenylpyrrole-2-carbaldehyde and o-phenylenediamine) by controlling only one reaction parameter (water content of the medium). It should be emphasized that the latter class of compounds (with an a/d arrangement) is previously unknown. If the allene group is introduced not into the starting compound, but during the reaction (in superbase media), a heterocyclic ensemble, 5-methylbenzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazines, with a different position of the methyl group is formed. Full article
(This article belongs to the Special Issue Polycyclic(hetero)aromatic Compounds)
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12 pages, 8127 KiB  
Article
Transformation of Thia[7]helicene to Aza[7]helicenes and [7]Helicene-like Compounds via Aromatic Metamorphosis
by Keisuke Uematsu, Chikara Hayasaka, Ko Takase, Keiichi Noguchi and Koji Nakano
Molecules 2022, 27(3), 606; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030606 - 18 Jan 2022
Cited by 6 | Viewed by 3129
Abstract
[n]Helicenes with helically twisted structures have attracted increasing interest owing to their unique properties. Therefore, it has been an important issue to develop facile synthetic methodologies which allow access to a variety of [n]helicenes. Here we report the synthesis [...] Read more.
[n]Helicenes with helically twisted structures have attracted increasing interest owing to their unique properties. Therefore, it has been an important issue to develop facile synthetic methodologies which allow access to a variety of [n]helicenes. Here we report the synthesis of [7]helicenes and [7]helicene-like compounds from the thia[7]helicene as a common starting material. Desulfurative dilithiation of the thia[7]helicene and the subsequent reaction with silicon and phosphorus electrophiles afforded the silole- and phosphole-fused [7]helicene-like compounds, respectively. The cyclopentadiene-fused [7]helicene-like compound and the pyrrole-fused aza[7]helicenes were also successfully synthesized via twofold SNAr reactions of the thia[7]helicene S,S-dioxide with the carbon and nitrogen nucleophiles, respectively. The thia[7]helicene S,S-dioxide showed a slightly red-shifted absorption spectrum than the parent thia[7]helicene, which was well demonstrated by the theoretical calculations. The substituents on the silicon atom of silole-fused [7]helicene-like compounds have little impact on the longest absorption maximum. Such little effect of the substituents on absorption properties was also observed for cyclopentadiene-fused [7]helicene-like compounds and aza[7]helicenes and was well demonstrated by the theoretical calculations. The thia[7]helicene S,S-dioxide and the silole-fused [7]helicene-like compound exhibited bright blue emission, and the cyclopentadiene-fused [7]helicene-like compound and the aza[7]helicenes showed strong violet emission. Each single enantiomer of the aza[7]helicenes showed circularly-polarized luminescence with the dissymmetry factors of 4.2~4.4 × 10−3. Full article
(This article belongs to the Special Issue Polycyclic(hetero)aromatic Compounds)
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