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Cycloaddition Chemistry
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Cycloaddition Chemistry

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

Deadline for manuscript submissions: closed (31 July 2014) | Viewed by 44402

Special Issue Editor

Dr. Robert A. Stockman

E-Mail Website
Guest Editor
School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UK
Interests: synthetic strategies; the total synthesis of natural products; new synthetic methods

Special Issue Information

Dear Colleagues,

Since Otto Diels and Kurt Alder first showed the power of cycloadditions, this area of chemistry has been in constant development. Cycloadditions over the past eight decades have proved to be a powerful tool for the synthetic chemist, allowing two or more bond constructions and the formation of multiple stereogenic centres in a single step, often with exquisite control of regiochemistry and stereochemistry. This Special Issue aims to highlight the most recent advances in the area of cycloaddition chemistry, from the areas of total synthesis, screening compound synthesis, asymmetric synthesis, heterocyclic chemistry, materials synthesis and bioconjugation.

Dr. Robert A. Stockman
Guest Editor

Submission

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a 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 1800 CHF (Swiss francs).

Keywords

  • cycloaddition
  • Diels-Alder
  • click chemistry
  • dipolar cycloaddition
  • catalytic asymmetric synthesis

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Published Papers (6 papers)

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Research

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378 KiB  
Article
Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
by Karl Hemming, Christopher S. Chambers, Faisal Jamshaid and Paul A. O'Gorman
Molecules 2014, 19(10), 16737-16756; https://doi.org/10.3390/molecules191016737 - 17 Oct 2014
Cited by 16 | Viewed by 9251
Abstract
The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of [...] Read more.
The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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825 KiB  
Article
Unusual Structure-Energy Correlations in Intramolecular Diels–Alder Reaction Transition States
by Justyna M. Żurek, Robert L. Rae, Martin J. Paterson and Magnus W. P. Bebbington
Molecules 2014, 19(10), 15535-15545; https://doi.org/10.3390/molecules191015535 - 29 Sep 2014
Cited by 3 | Viewed by 6654
Abstract
Detailed analysis of calculated data from an experimental/computational study of intramolecular furan Diels–Alder reactions has led to the unusual discovery that the mean contraction of the newly forming C-C σ-bonds from the transition state to the product shows a linear correlation with both [...] Read more.
Detailed analysis of calculated data from an experimental/computational study of intramolecular furan Diels–Alder reactions has led to the unusual discovery that the mean contraction of the newly forming C-C σ-bonds from the transition state to the product shows a linear correlation with both reaction Gibbs free energies and reverse energy barriers. There is evidence for a similar correlation in other intramolecular Diels–Alder reactions involving non-aromatic dienes. No such correlation is found for intermolecular Diels–Alder reactions. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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781 KiB  
Article
Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
by Roberto Romeo, Caterina Carnovale, Salvatore V. Giofrè, Giulia Monciino, Maria A. Chiacchio, Claudia Sanfilippo and Beatrice Macchi
Molecules 2014, 19(9), 14406-14416; https://doi.org/10.3390/molecules190914406 - 12 Sep 2014
Cited by 15 | Viewed by 5837
Abstract
Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (−)12a and diethyl{[(3R,5 [...] Read more.
Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (−)12a and diethyl{[(3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (+)12b have been synthesized. The obtained compounds showed no cytotoxic activity versus the U937 cell line in comparison with AZT, and were poorly able to inhibit HIV infection in vitro. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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1572 KiB  
Article
Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes
by Klaus Banert, Sandra Bochmann, Andreas Ihle, Oliver Plefka, Florian Taubert, Tina Walther, Marcus Korb, Tobias Rüffer and Heinrich Lang
Molecules 2014, 19(9), 14022-14035; https://doi.org/10.3390/molecules190914022 - 5 Sep 2014
Cited by 8 | Viewed by 8414
Abstract
Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes [...] Read more.
Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b–d, orthoesters 4a–c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 via retro-Brook rearrangement of the dipolar intermediate 2c. In all cases, the products are formed with perfect atom economy. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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344 KiB  
Article
Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline
by Misal Giuseppe Memeo, Francesco Lapolla, Bruna Bovio and Paolo Quadrelli
Molecules 2014, 19(6), 8661-8678; https://doi.org/10.3390/molecules19068661 - 24 Jun 2014
Cited by 4 | Viewed by 6217
Abstract
The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxaza-norborn-5-ene were easily prepared and elaborated into a novel class of uracil-based scaffolds. The key-synthetic step is the nucleophilic substitution at the sp2 carbon atom of the bromoisoxazoline three-dimensional heterocycles. The protocol to perform [...] Read more.
The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxaza-norborn-5-ene were easily prepared and elaborated into a novel class of uracil-based scaffolds. The key-synthetic step is the nucleophilic substitution at the sp2 carbon atom of the bromoisoxazoline three-dimensional heterocycles. The protocol to perform the nucleophilic substitution of uracil anions was optimized and adapted to the steric requirements of the substrates. A library of pyrimidine derivatives was prepared in very good yields and the products were fully characterized. They are proposed as nucleoside analogues and as synthons for β-turn motifs within PNA structures. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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Review

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760 KiB  
Review
Cycloaddition of 1,3-Butadiynes: Efficient Synthesis of Carbo- and Heterocycles
by Tauqir A. Nizami and Ruimao Hua
Molecules 2014, 19(9), 13788-13802; https://doi.org/10.3390/molecules190913788 - 3 Sep 2014
Cited by 24 | Viewed by 7514
Abstract
Cycloaddition reactions of alkynes are elegant, atom-efficient transformations for the synthesis of carbo- and heterocycles, mostly aromatic, involving the construction of challenging skeletons of complex molecules. Therefore significant efforts have recently been devoted to the development of novel methodologies, efficient strategies and different [...] Read more.
Cycloaddition reactions of alkynes are elegant, atom-efficient transformations for the synthesis of carbo- and heterocycles, mostly aromatic, involving the construction of challenging skeletons of complex molecules. Therefore significant efforts have recently been devoted to the development of novel methodologies, efficient strategies and different catalytic systems to broaden the scope of these reactions. We summarize in this review the recent advances in the cycloaddition reactions of 1,3-butadiynes to provide facile and reliable approaches to various functionalized carbo- and heterocycles. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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