Cycloaddition Reactions at the Beginning of the Second Millennium

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

Deadline for manuscript submissions: 30 June 2024 | Viewed by 4176

Special Issue Editors


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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

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Guest Editor
Dipartimento di Chimica ”Ugo Schiff”, Università degli Studi di Firenze, 50019 Sesto Fiorentino, Firenze, Italy
Interests: organic chemistry; cycloaddition reactions; catalysis

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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

Manuscript Submission Information

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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

Published Papers (3 papers)

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Research

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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
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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 212 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 Second 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 - 02 Dec 2022
Cited by 1 | Viewed by 1373
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 Second Millennium)
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Review

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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 - 04 Mar 2024
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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 Second Millennium)
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