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Cycloaddition Reactions in Organic Synthesis
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Cycloaddition Reactions in Organic Synthesis

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

Deadline for manuscript submissions: closed (30 November 2010) | Viewed by 65462

Special Issue Editor

Dr. Janis Louie

E-Mail
Guest Editor
Department of Chemisty, the University of Utah, 315 S, 1400 East Salt Lake City, UT 84112, USA
Interests: catalytic activation of heterocumulenes; Ni-catalyzed rearrangements: rapid entry to carbocycles; CO2 sequestering agents

Special Issue Information

Dear Colleagues,

Cycloaddition reactions provide rapid access to natural and unnatural compounds of medicinal interest or intermediates useful for functional materials. In general, cycloadditions represent an efficient entry to ring systems and require readily available starting materials. In addition, many cycloaddition reactions tolerate a wide variety of functional groups. The focus of this special issue is to present papers that cover both fundamental and applied contributions in this field. Special attention will be paid to the development of new methodologies, mechanistic analysis of existing methodologies, and applications of cycloaddition reactions toward the synthesis of pharmalogically or industrially relevant materials.

Prof. Dr. Janis Louie
Guest Editor

Keywords

  • cycloaddition
  • metal catalyzed organic transformations
  • organocatalyzed transformations
  • asymmetric catalysis
  • mechanistic analysis
  • medicinal chemistry

Published Papers (6 papers)

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Research

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228 KiB  
Article
Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives
by Nagwa Mohamed Mahrous Hamada and Essam Mohamed Sharshira
Molecules 2011, 16(3), 2304-2312; https://doi.org/10.3390/molecules16032304 - 09 Mar 2011
Cited by 34 | Viewed by 8199
Abstract
Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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211 KiB  
Article
Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity
by Ameen Ali Abu-Hashem and Mohamed M. Youssef
Molecules 2011, 16(3), 1956-1972; https://doi.org/10.3390/molecules16031956 - 25 Feb 2011
Cited by 75 | Viewed by 9989
Abstract
6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d with [...] Read more.
6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d with phosphorus oxychloride yielded 6-chlorofurochromenylidenepyrimidinamines 4a–d, which were reacted with secondary amines to afford furochromenylideneamino-2,6-disubstituted pyrimidin-4-ones 5a–d. In addition, reaction of 5a–d with 3-chloropentane-2,4-dione gave 3-chloro-furochromenylpyrimidopyrimidines 6a–d. The latter were reacted with piperazine and morpholine to give 1-(furochromenyl)-pyrimidopyrimidine-3,6,8-triylpiperazines or -3,6,8-triylmorpholines 7a–d. The chemical structures of the newly synthesized compound ware characterized by IR, 1H-NMR, 13C-NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of them, particularly 3–7, exhibited promising activities. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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286 KiB  
Article
Rhodium-Catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes
by Teruyuki Kondo, Masatsugu Niimi, Yuki Yoshida, Kenji Wada, Take-aki Mitsudo, Yu Kimura and Akio Toshimitsu
Molecules 2010, 15(6), 4189-4200; https://doi.org/10.3390/molecules15064189 - 09 Jun 2010
Cited by 10 | Viewed by 7386
Abstract
A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh [...] Read more.
A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh3)3, and are highly dependent on the structure and reactivity of the starting ketenes. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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Review

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918 KiB  
Review
Solid-State [2+2] Photodimerization and Photopolymerization of α,ω-Diarylpolyene Monomers: Effective Utilization of Noncovalent Intermolecular Interactions in Crystals
by Yoriko Sonoda
Molecules 2011, 16(1), 119-148; https://doi.org/10.3390/molecules16010119 - 28 Dec 2010
Cited by 100 | Viewed by 15721
Abstract
[2+2] Photocycloaddition of olefins is a very useful reaction in synthetic organic chemistry to obtain cyclobutane-containing molecules, which are almost inaccessible by other methods. The reaction, when performed in the crystalline state, occurs more efficiently and selectively than in homogeneous solution due to [...] Read more.
[2+2] Photocycloaddition of olefins is a very useful reaction in synthetic organic chemistry to obtain cyclobutane-containing molecules, which are almost inaccessible by other methods. The reaction, when performed in the crystalline state, occurs more efficiently and selectively than in homogeneous solution due to tight and regular molecular arrangement in the crystal state. Despite numerous examples for the solid-state [2+2] photodimerization of monoenes, however, it is still a challenge to prepare not only dimers but also higher oligomers and polymers from conjugated polyenes, which have multiple reactive double bonds in a molecule. In our recent studies of the solid-state photoreactions of α,ω-diarylpolyenes, noncovalent intermolecular interactions in crystals were effectively utilized to prealign molecules in stacking arrangements, suitable for the [2+2] reaction. With appropriate ring-substituents, [2+2] photodimerization and photopolymerization of the polyenes took place, although the degree of polymerization was relatively low. This review will describe the details of these reactions. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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708 KiB  
Review
Application of Cycloaddition Reactions to the Syntheses of Novel Boron Compounds
by Yinghuai Zhu, Xiao Siwei, John A. Maguire and Narayan S. Hosmane
Molecules 2010, 15(12), 9437-9449; https://doi.org/10.3390/molecules15129437 - 21 Dec 2010
Cited by 5 | Viewed by 10688
Abstract
This review covers the application of cycloaddition reactions in forming the boron-containing compounds such as symmetric star-shaped boron-enriched dendritic molecules, nano-structured boron materials and aromatic boronic esters. The resulting boron compounds are potentially important reagents for both materials science and medical applications such [...] Read more.
This review covers the application of cycloaddition reactions in forming the boron-containing compounds such as symmetric star-shaped boron-enriched dendritic molecules, nano-structured boron materials and aromatic boronic esters. The resulting boron compounds are potentially important reagents for both materials science and medical applications such as in boron neutron capture therapy (BNCT) in cancer treatment and as drug delivery agents and synthetic intermediates for carbon-carbon cross-coupling reactions. In addition, the use of boron cage compounds in a number of cycloaddition reactions to synthesize unique aromatic species will be reviewed briefly. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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224 KiB  
Review
[2+2+2] Cycloaddition Reactions of Macrocyclic Systems Catalyzed by Transition Metals. A Review
by Anna Pla-Quintana and Anna Roglans
Molecules 2010, 15(12), 9230-9251; https://doi.org/10.3390/molecules15129230 - 15 Dec 2010
Cited by 61 | Viewed by 12719
Abstract
Polyalkyne and enediyne azamacrocycles are prepared from arenesulfonamides and various alkyne and alkene derivatives either under basic or neutral conditions. The new family of macrocyclic substrates is tested in the [2+2+2] cycloaddition reaction. Several catalysts are used for the cycloisomerization reaction, and their [...] Read more.
Polyalkyne and enediyne azamacrocycles are prepared from arenesulfonamides and various alkyne and alkene derivatives either under basic or neutral conditions. The new family of macrocyclic substrates is tested in the [2+2+2] cycloaddition reaction. Several catalysts are used for the cycloisomerization reaction, and their enantioinduction is evaluated as appropriate. The effect of the structural features of the macrocycles, namely the ring size, substituents in precise positions and the number and type of unsaturations, on the [2+2+2] cycloaddition reaction has also been studied. Full article
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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