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Advances in Heterocyclic Synthesis
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Advances in Heterocyclic Synthesis

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

Deadline for manuscript submissions: 31 August 2024 | Viewed by 6544

Special Issue Editor

Prof. Dr. Francesca Marini

E-Mail Website
Guest Editor
Department of Pharmaceutical Sciences, University of Perugia Via del Liceo 1, 06100 Perugia, Italy
Interests: heterocycles; stereoselective synthesis; one-pot reactions; multicomponent reactions; organocatalytic methods; organoselenium chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Heterocycles have a great impact in several areas of chemical research such as organic, bioorganic, medicinal and material chemistry. Such compounds are valuable ligands, auxiliaries or catalysts as well as key synthetic intermediates in organic synthesis. Moreover, heterocycles represent structural cores of bioactive natural products, pharmaceuticals, agrochemicals, polymers and materials. Given the widespread interest, a number of new methodologies for the assembling and the functionalization of heterocycles continues to appear every year in the literature. This Special Issue aims to present new developments in the field of heterocyclic chemistry. Potential topics include (but are not limited to) sustainable synthesis of heterocyclic compounds, one-pot or multicomponent reactions, synthesis of biologically relevant heterocycles.

Prof. Dr. Francesca Marini
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

  • heterocycles
  • stereoselective synthesis
  • sustainable synthesis
  • one-pot reactions
  • multicomponent reactions
  • catalysis

Published Papers (7 papers)

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Research

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17 pages, 2498 KiB  
Article
Using Quinolin-4-Ones as Convenient Common Precursors for a Metal-Free Total Synthesis of Both Dubamine and Graveoline Alkaloids and Diverse Structural Analogues
by Rodrigo Abonia, Lorena Cabrera, Diana Arteaga, Daniel Insuasty, Jairo Quiroga, Paola Cuervo and Henry Insuasty
Molecules 2024, 29(9), 1959; https://doi.org/10.3390/molecules29091959 - 25 Apr 2024
Viewed by 412
Abstract
The Rutaceae family is one of the most studied plant families due to the large number of alkaloids isolated from them with outstanding biological properties, among them the quinoline-based alkaloids Graveoline 1 and Dubamine 2. The most common methods for the synthesis [...] Read more.
The Rutaceae family is one of the most studied plant families due to the large number of alkaloids isolated from them with outstanding biological properties, among them the quinoline-based alkaloids Graveoline 1 and Dubamine 2. The most common methods for the synthesis of alkaloids 1 and 2 and their derivatives involves cycloaddition reactions or metal-catalyzed coupling processes but with some limitations in scope and functionalization of the quinoline moiety. As a continuation of our current studies on the synthesis and chemical transformation of 2-aminochalcones, we are reporting here an efficient metal-free approach for the total synthesis of alkaloids 1 and 2 along with their analogues with structural diversity, through a two-step sequence involving intramolecular cyclization, oxidation/aromatization, N-methylation and oxidative C-C bond processes, starting from dihydroquinolin-4-ones as common precursors for the construction of the structures of both classes of alkaloids. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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15 pages, 3371 KiB  
Article
Electrochemical Radical Tandem Difluoroethylation/Cyclization of Unsaturated Amides to Access MeCF2-Featured Indolo/Benzoimidazo [2,1-a]Isoquinolin-6(5H)-ones
by Yunfei Tian, Dongyu Guo, Luping Zheng, Shaolu Yang, Ningning Zhang, Weijun Fu and Zejiang Li
Molecules 2024, 29(5), 973; https://doi.org/10.3390/molecules29050973 - 22 Feb 2024
Viewed by 494
Abstract
A metal-free electrochemical oxidative difluoroethylation of 2-arylbenzimidazoles was accomplished, which provided an efficient strategy for the synthesis of MeCF2-containing benzo[4,5]imidazo[2,1-a]-isoquinolin-6(5H)-ones. In addition, the method also enabled the efficient construction of various difluoroethylated indolo[2,1-a]isoquinolin-6(5H)-ones. [...] Read more.
A metal-free electrochemical oxidative difluoroethylation of 2-arylbenzimidazoles was accomplished, which provided an efficient strategy for the synthesis of MeCF2-containing benzo[4,5]imidazo[2,1-a]-isoquinolin-6(5H)-ones. In addition, the method also enabled the efficient construction of various difluoroethylated indolo[2,1-a]isoquinolin-6(5H)-ones. Notably, this electrochemical synthesis protocol proceeded well under mild conditions without metal catalysts or exogenous additives/oxidants added. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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19 pages, 26194 KiB  
Article
Reactivity and Stability of (Hetero)Benzylic Alkenes via the Wittig Olefination Reaction
by Ajmir Khan, Mohammed G. Sarwar and Sher Ali
Molecules 2024, 29(2), 501; https://doi.org/10.3390/molecules29020501 - 19 Jan 2024
Viewed by 744
Abstract
Wittig olefination at hetero-benzylic positions for electron-deficient and electron-rich heterocycles has been studied. The electronic effects of some commonly used protective groups associated with the N-heterocycles were also investigated for alkenes obtained in the context of the widely employed Wittig olefination reaction. [...] Read more.
Wittig olefination at hetero-benzylic positions for electron-deficient and electron-rich heterocycles has been studied. The electronic effects of some commonly used protective groups associated with the N-heterocycles were also investigated for alkenes obtained in the context of the widely employed Wittig olefination reaction. It was observed that hetero-benzylic positions of the pyridine, thiophene and furan derivatives were stable after Wittig olefination. Similarly, electron-withdrawing groups (EWGs) attached to N-heterocycles (indole and pyrrole derivatives) directly enhanced the stability of the benzylic position during and after Wittig olefination, resulting in the formation of stable alkenes. Conversely, electron-donating group (EDG)-associated N-heterocycles boosted the reactivity of benzylic alkene, leading to lower yields or decomposition of the olefination products. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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15 pages, 3362 KiB  
Article
(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study
by Grzegorz Mlostoń, Katarzyna Urbaniak, Marcin Palusiak, Zbigniew J. Witczak and Ernst-Ulrich Würthwein
Molecules 2023, 28(21), 7348; https://doi.org/10.3390/molecules28217348 - 30 Oct 2023
Viewed by 910
Abstract
The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of the levoglucosenone molecule, yielding the corresponding, five-membered cycloadducts. In contrast to the ‘classic’ C(Ph),N(Ph) nitrile imine, reactions with fluorinated C(CF3 [...] Read more.
The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of the levoglucosenone molecule, yielding the corresponding, five-membered cycloadducts. In contrast to the ‘classic’ C(Ph),N(Ph) nitrile imine, reactions with fluorinated C(CF3),N(Ar) analogues lead to stable pyrazolines in a chemo- and stereoselective manner. Based on the result of X-ray single crystal diffraction analysis, their structures were established as exo-cycloadducts with the location of the N-Ar terminus of the 1,3-dipole at the α-position of the enone moiety. The DFT computation demonstrated that the observed reaction pathway results from the strong dominance of kinetic control over thermodynamic control. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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24 pages, 3811 KiB  
Article
Novel Strigolactone Mimics That Modulate Photosynthesis and Biomass Accumulation in Chlorella sorokiniana
by Daria Gabriela Popa, Florentina Georgescu, Florea Dumitrascu, Sergiu Shova, Diana Constantinescu-Aruxandei, Constantin Draghici, Lucian Vladulescu and Florin Oancea
Molecules 2023, 28(20), 7059; https://doi.org/10.3390/molecules28207059 - 12 Oct 2023
Cited by 1 | Viewed by 984
Abstract
In terrestrial plants, strigolactones act as multifunctional endo- and exo-signals. On microalgae, the strigolactones determine akin effects: induce symbiosis formation with fungi and bacteria and enhance photosynthesis efficiency and accumulation of biomass. This work aims to synthesize and identify strigolactone mimics that promote [...] Read more.
In terrestrial plants, strigolactones act as multifunctional endo- and exo-signals. On microalgae, the strigolactones determine akin effects: induce symbiosis formation with fungi and bacteria and enhance photosynthesis efficiency and accumulation of biomass. This work aims to synthesize and identify strigolactone mimics that promote photosynthesis and biomass accumulation in microalgae with biotechnological potential. Novel strigolactone mimics easily accessible in significant amounts were prepared and fully characterized. The first two novel compounds contain 3,5-disubstituted aryloxy moieties connected to the bioactive furan-2-one ring. In the second group of compounds, a benzothiazole ring is connected directly through the cyclic nitrogen atom to the bioactive furan-2-one ring. The novel strigolactone mimics were tested on Chlorella sorokiniana NIVA-CHL 176. All tested strigolactones increased the accumulation of chlorophyll b in microalgae biomass. The SL-F3 mimic, 3-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)-3H-benzothiazol-2-one (7), proved the most efficient. This compound, applied at a concentration of 10−7 M, determined a significant biomass accumulation, higher by more than 15% compared to untreated control, and improved the quantum yield efficiency of photosystem II. SL-F2 mimic, 5-(3,5-dibromophenoxy)-3-methyl-5H-furan-2-one (4), applied at a concentration of 10−9 M, improved protein production and slightly stimulated biomass accumulation. Potential utilization of the new strigolactone mimics as microalgae biostimulants is discussed. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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11 pages, 1512 KiB  
Article
Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-a]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile
by Loana I. Monzon, Nicole C. M. Rocha, Gabriela T. Quadros, Pâmela P. P. Nunes, Roberta Cargnelutti, Raquel G. Jacob, Eder J. Lenardão, Gelson Perin and Daniela Hartwig
Molecules 2023, 28(13), 5036; https://doi.org/10.3390/molecules28135036 - 27 Jun 2023
Cited by 1 | Viewed by 967
Abstract
A general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions were conducted using a mixture of dimethylsulfoxide and water [...] Read more.
A general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions were conducted using a mixture of dimethylsulfoxide and water (7:3) as solvent at 80 °C for 4 h. This new methodology presents a good functional group tolerance to electron-deficient and electron-rich substituents, affording a total of twelve different 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines selectively in moderate to excellent yields. The structure of the synthesized 4-(phenylselanyl)tetrazolo[1,5-a]quinoline was confirmed by X-ray analysis. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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Review

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42 pages, 11760 KiB  
Review
Synthesis of Nitrogen-Containing Heterocyclic Scaffolds through Sequential Reactions of Aminoalkynes with Carbonyls
by Antonio Arcadi, Valerio Morlacci and Laura Palombi
Molecules 2023, 28(12), 4725; https://doi.org/10.3390/molecules28124725 - 12 Jun 2023
Cited by 2 | Viewed by 1394
Abstract
Sequential reactions of aminoalkynes represent a powerful tool to easily assembly biologically important polyfunctionalized nitrogen heterocyclic scaffolds. Metal catalysis often plays a key role in terms of selectivity, efficiency, atom economy, and green chemistry of these sequential approaches. This review examines the existing [...] Read more.
Sequential reactions of aminoalkynes represent a powerful tool to easily assembly biologically important polyfunctionalized nitrogen heterocyclic scaffolds. Metal catalysis often plays a key role in terms of selectivity, efficiency, atom economy, and green chemistry of these sequential approaches. This review examines the existing literature on the applications of reactions of aminoalkynes with carbonyls, which are emerging for their synthetic potential. Aspects concerning the features of the starting reagents, the catalytic systems, alternative reaction conditions, pathways and possible intermediates are provided. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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