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Cycloaddition Reactions at the Beginning of the Third Millennium
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Cycloaddition Reactions at the Beginning of the Third Millennium

A special issue of Reactions (ISSN 2624-781X).

Deadline for manuscript submissions: closed (30 November 2024) | Viewed by 9956

Special Issue Editors

Prof. Dr. Donatella Giomi

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Guest Editor
Chemistry Department "Ugo Schiff", University of Florence, Via della Lastruccia 3-13, 50019 Sesto Fiorentino, FI, Italy
Interests: nitrogen heterocycles; pyridazines; nitroisoxazoles; pyridyl- and quinolyl-carbinols; metal-free reductions; hantzsch ester 1,4-dihydropyridine mimics; nitro compounds; indolizidine derivatives; bioDiesel; biomass valorization
Prof. Dr. Alberto Brandi

E-Mail Website
Guest Editor
Dipartimento di Chimica ”Ugo Schiff”, Università degli Studi di Firenze, 50019 Sesto Fiorentino, Firenze, Italy
Interests: organic chemistry; cycloaddition reactions; catalysis
Prof. Dr. Fabrizio Machetti

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Guest Editor
Istituto di Chimica dei Composti Organometallici del Consiglio Nazionale delle Ricerche c/o Dipartimento di Chimica “U. Schiff”, Università di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Firenze, Italy
Interests: catalysis; organocatalysis; heterocycles; synthetic methodologies; materials

Special Issue Information

Dear Colleagues,

Almost a century after the discovery of the Diels–Alder cycloaddition, this kind of pericyclic process continues to be a very efficient tool in synthetic organic chemistry and shows significant and widespread applications in different chemistry areas, from traditional organic synthesis to medicinal chemistry, materials chemistry, and so on. These reactions are beneficial to chemists because they provide valuable cyclic compounds, often in a simple manner and with high and predictable regio- and stereochemistry in addition to high atom economy. These appealing features make cycloadditions privileged processes in organic synthesis.

In this context, this Special Issue in Reactions aims to collect recent results concerning the applications of [4+2] cycloadditions, namely Diels–Alder, hetero Diels–Alder, and 1,3-dipolar cycloadditions, as well as [2+2] processes. The use of more efficient, green, and sustainable experimental conditions is strongly pursued to improve both the environmental aspects and the synthesis of carbo- and heterocycles with noteworthy applications in the natural, pharmacological, biological, and materials domains.

All researchers working in this field are invited to contribute to this issue emphasizing synthetic and methodological results, as well as mechanistic and/or theoretical aspects. Review articles by experts in the field are also welcome.

Prof. Dr. Donatella Giomi
Prof. Dr. Alberto Brandi
Prof. Dr. Fabrizio Machetti
Guest Editors

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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. Reactions is an international peer-reviewed open access quarterly 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 1000 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

  • Diels–alder reactions
  • hetero Diels–alder reactions
  • 1,3-dipolar cycloadditions
  • [2+2]-cycloadditions
  • selectivity
  • photochemical reactions
  • theoretical studies
  • atom economy
  • sustainable approaches
  • heterocycle synthesis

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Published Papers (7 papers)

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Research

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14 pages, 2704 KiB  
Article
Highly Regioselective 1,3-Dipolar Cycloaddition of Nitrilimines and Thioaurones Towards Spiro-2-Pyrazolines: Synthesis, Characterization, and Mechanistic Study
by Mohamed Bakhouch, Bouchra Es-Sounni, Ayoub Ouaddi, Khaoula Oudghiri, Mohammed Chalkha, Lahoucine Bahsis, Taoufiq Benali, Mohamed Bourass, Rabiaa Fdil, Mohamed Akhazzane and Mohamed El Yazidi
Reactions 2024, 5(4), 1066-1079; https://doi.org/10.3390/reactions5040056 (registering DOI) - 14 Dec 2024
Abstract
In this paper, we report a regiospecific 1,3-dipolar cycloaddition (1,3-DC) reaction of nitrilimines with thioaurone derivatives that afforded the hitherto unreported spiropyrazolines. Spectroscopic and spectrometric data were utilized to confirm the structure of all products and elucidate the reaction’s regiochemistry. A mechanistic study [...] Read more.
In this paper, we report a regiospecific 1,3-dipolar cycloaddition (1,3-DC) reaction of nitrilimines with thioaurone derivatives that afforded the hitherto unreported spiropyrazolines. Spectroscopic and spectrometric data were utilized to confirm the structure of all products and elucidate the reaction’s regiochemistry. A mechanistic study was performed within the Molecular Electron Density Theory (MEDT) at the B3LYP/6-311G(d,p) computational level to explain the regioselectivity observed. The electron localization function (ELF) topological analysis confirms the carbenoid-type (cb-type) mechanism of the cycloaddition reactions between nitrilimines and thioaurones. The intermolecular interactions between reagents in this reaction account for the regioselectivity observed experimentally. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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19 pages, 4030 KiB  
Article
Diels–Alder Cycloaddition of N-Azobenzene Maleimides with Furan and Electrochemical Study of Redox Reactions
by David Fernando Venegas-Villalvazo, David Abraham Figueroa-Hernández, Armando Pineda-Contreras, José Manuel Flores-Alvarez, Héctor García-Ortega and Juan Saulo González-González
Reactions 2024, 5(4), 928-946; https://doi.org/10.3390/reactions5040049 - 15 Nov 2024
Viewed by 480
Abstract
This work reports the synthesis of aminoazobenzene compounds derived from 3,5-dimethylaniline (1a–1f) via a diazo-coupling reaction with aromatic amines. These aminoazobenzenes were acylated with maleic anhydride to obtain the corresponding maleimides (2a–2f). The maleimides were [...] Read more.
This work reports the synthesis of aminoazobenzene compounds derived from 3,5-dimethylaniline (1a–1f) via a diazo-coupling reaction with aromatic amines. These aminoazobenzenes were acylated with maleic anhydride to obtain the corresponding maleimides (2a–2f). The maleimides were then used as dienophiles in a Dies–Alder cycloaddition reaction with furan as the diene, yielding the adducts (3a–3f). All synthesized compounds were characterized using FTIR, 1H, and 13C NMR spectroscopy. Additionally, electrochemical studies using cyclic voltammetry were conducted to determine the oxidation–reduction reactions present in the compounds. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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18 pages, 4187 KiB  
Article
Reduction and Cycloaddition of Heteroalkenes at Ga(I) Bisamide Center
by Vladimir A. Dodonov, Olga A. Kushnerova, Evgeny V. Baranov and Igor L. Fedushkin
Reactions 2024, 5(1), 213-230; https://doi.org/10.3390/reactions5010009 - 20 Feb 2024
Cited by 1 | Viewed by 1864
Abstract
The reactivity of the complex [(dpp-bian)GaNa(DME)2] (1) (dpp-bian = 1,2-bis[(2,6-di-isopropylphenyl)imino]acenaphthene) towards isocyanates, benzophenone, diphenylketene, and 1,2-dibenzylidenehydrazine has been studied. Treatment of 1 with isocyanates led to derivatives of imidoformamide [(dpp-bian)Ga{C(=NPh)2}2–NPh][Na(DME)3] (2), [...] Read more.
The reactivity of the complex [(dpp-bian)GaNa(DME)2] (1) (dpp-bian = 1,2-bis[(2,6-di-isopropylphenyl)imino]acenaphthene) towards isocyanates, benzophenone, diphenylketene, and 1,2-dibenzylidenehydrazine has been studied. Treatment of 1 with isocyanates led to derivatives of imidoformamide [(dpp-bian)Ga{C(=NPh)2}2–NPh][Na(DME)3] (2), biuret [(dpp-bian)Ga(NCy)2(CO)2NCy][Na(DME)] (3), or carbamic acids [(dpp-bian)GaN(Cy)C(O)O]2[Na(THF)(Et2O)] (4), [(dpp-bian)GaC(=NCy)N(Cy)C(O)O][Na(Py)3] (5). Treatment of 1 with 2 equiv. of Ph2CO resulted in gallium pinacolate [(dpp-bian)GaO(CPh2)2O][Na(Py)2] (9), while the reaction of 1 with 2 equiv. Ph2CCO gave divinyl ether derivative [(dpp-bian)Ga{C(=CPh2)O}2][Na(DME)3] (10). Complex 1 treated with 2 equiv. 1,2-dibenzylidenehydrazine underwent [1+2+2] cycloaddition to give C–C coupling product [(dpp-bian)Ga{N(NCHPh)}2(CHPh)2][Na(DME)3] (11). When complex 1 was sequentially treated with 1 equiv. of 1,2-dibenzylidenehydrazine and 1 equiv. of pyridine or pyridine-d5; it gave [1+2+2] cycloaddition product [(dpp-bian)GaN(NCHPh)C(Ph)CN][Na(DME)3] (12). Compounds 2–12 were characterized by NMR and IR spectroscopy, and their molecular structures were established by single-crystal X-ray diffraction analysis. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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10 pages, 1675 KiB  
Article
Synthesis and Characterization of Multiple Functionalized Cyclohexanone Using Diels–Alder Reaction of α-Nitrocinnamate
by Takumi Hamada, Kento Iwai and Nagatoshi Nishiwaki
Reactions 2022, 3(4), 615-624; https://doi.org/10.3390/reactions3040041 - 2 Dec 2022
Cited by 2 | Viewed by 1834
Abstract
A systematic study of the Diels–Alder reaction of α-nitrocinnamate was performed. The reaction of p-substituted α-nitrocinnamate with 2,3-dimethyl-1,3-butadienes smoothly proceeded regardless of the p-substituent, which was either an electron-donating or -withdrawing group. A control reaction revealed that α-nitrocinnamate isomerized during the [...] Read more.
A systematic study of the Diels–Alder reaction of α-nitrocinnamate was performed. The reaction of p-substituted α-nitrocinnamate with 2,3-dimethyl-1,3-butadienes smoothly proceeded regardless of the p-substituent, which was either an electron-donating or -withdrawing group. A control reaction revealed that α-nitrocinnamate isomerized during the reaction. Danishefsly’s diene (1-methoxy-3-trimethylsiloxy-1,3-butadiene) facilitated cycloaddition under mild conditions to afford a cycloadduct without the alternation of the diastereomeric ratio. Moreover, the desilylation of the cycloadduct furnished multiple functionalized cyclohexanones. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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Review

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37 pages, 8154 KiB  
Review
Importance of the CuAAC Reaction in the Synthesis of Platinum Complexes with 1,4-Disubstituted-1H-1,2,3-triazoles: A Review of Their Anticancer Activity
by Delia Hernández-Romero, Sharon Rosete-Luna, Enrique Méndez-Bolaina, Elena de la C. Herrera-Cogco, Luis P. Amador-Gómez, Anell Soto-Contreras, José M. Rivera-Villanueva and Raúl Colorado-Peralta
Reactions 2024, 5(4), 947-983; https://doi.org/10.3390/reactions5040050 - 24 Nov 2024
Viewed by 696
Abstract
Despite multiple advances in treatment and prevention, cancer remains one of the leading causes of death worldwide. Chemotherapy remains the most effective method for cancer treatment. However, commercial chemotherapeutic drugs have limited efficacy, severe side effects, and acquired resistance. Therefore, the scientific community [...] Read more.
Despite multiple advances in treatment and prevention, cancer remains one of the leading causes of death worldwide. Chemotherapy remains the most effective method for cancer treatment. However, commercial chemotherapeutic drugs have limited efficacy, severe side effects, and acquired resistance. Therefore, the scientific community has devoted a great effort to designing new, more effective, and cheaper drugs. In this sense, copper-catalyzed azide-alkyne cycloaddition reactions (CuAAC) provide 1,4-disubstituted 1H-1,2,3-triazoles in high yields without forming by-products. This reaction allows the easy, efficient, functional, ordered, rapid, selective, and specific joining of small molecules, giving rise to more complex molecules. The CuACC reaction simplifies the synthesis processes, accelerating the discovery of new chemotherapeutic agents by allowing the joining of commercial platinum drugs, slightly altering their structure, or creating new molecules with improved properties. This work shows the importance of CuAAC reactions in the search for new metallodrugs with possible anticancer activity. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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75 pages, 60182 KiB  
Review
Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update
by Franca Maria Cordero, Donatella Giomi and Fabrizio Machetti
Reactions 2024, 5(3), 492-566; https://doi.org/10.3390/reactions5030026 - 16 Aug 2024
Cited by 1 | Viewed by 1270
Abstract
The present review is a comprehensive update of the synthesis of monocyclic β-lactams via cycloaddition reactions. According to the IUPAC definition of cycloaddition, both elementary and stepwise processes (formal cycloadditions) have been considered. The years 2019–2022 are covered by the cited literature. The [...] Read more.
The present review is a comprehensive update of the synthesis of monocyclic β-lactams via cycloaddition reactions. According to the IUPAC definition of cycloaddition, both elementary and stepwise processes (formal cycloadditions) have been considered. The years 2019–2022 are covered by the cited literature. The focus of the review is on synthetic aspects with emphasis on the structural scope, reaction conditions, mechanistic aspects, and selectivity results. Selected significant data related to biological activities and synthetic applications are also highlighted. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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15 pages, 5560 KiB  
Review
Bioorthogonal “Click” Cycloadditions: A Toolkit for Modulating Polymers and Nanostructures in Living Systems
by Irene Lepori, Yavuz Oz, Jungkyun Im, Nandan Ghosh, Mohuya Paul, Ulrich S. Schubert and Stefano Fedeli
Reactions 2024, 5(1), 231-245; https://doi.org/10.3390/reactions5010010 - 4 Mar 2024
Cited by 2 | Viewed by 2322
Abstract
“Click” cycloadditions offer effective pathways for the modifications of supramolecular structures, polymers, and nanomaterials. These reactions include bioorthogonal mechanisms that do not interfere with the biological processes, providing a type of chemistry to operate directly in living environments, such as cells and animals. [...] Read more.
“Click” cycloadditions offer effective pathways for the modifications of supramolecular structures, polymers, and nanomaterials. These reactions include bioorthogonal mechanisms that do not interfere with the biological processes, providing a type of chemistry to operate directly in living environments, such as cells and animals. As a result, the “click” cycloadditions represent highly and selective tools for tailoring the properties of nanomedicine scaffolds, expanding the efficacy of multiple therapeutic strategies. We focused this minireview on the bioorthogonal cycloadditions, presenting an insight into the strategies to modify nanostructured biomedical scaffolds inside living systems. We organized the contributions according to the three main mechanisms of “click” cycloadditions: strain-promoted sydnone-alkyne, tetrazine ligation, and strain-promoted [3+2] azido-alkyne. Full article
(This article belongs to the Special Issue Cycloaddition Reactions at the Beginning of the Third Millennium)
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