Substituted azulenes, valuable structures for electronic devices and pharmaceuticals, have been synthesized by the platinum(II)-catalyzed intramolecular ring-expanding cycloisomerization of 1-en-3-yne with ortho-disubstituted benzene. This novel method provides an alternative route for the efficient synthesis of substituted azulenes. The reaction mechanism of selected catalytic transformations was explored using density functional calculations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol502270q | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
One Step Synthesis of 4,6,8-Trimethoxyazulenes - a General Building Block for 2-Functionalized Azulenes.
Chemistry
January 2025
Ruprecht Karls Universitat Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120, Heidelberg, GERMANY.
Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselectivity for electrophilic substitutions, which enables facile electrophilic 2-substitution with iodine, bromine, chlorine, selenium or sulfur. Especially the 2-haloazulenes which can usually only be obtained through lengthy multistep syntheses are valuable building blocks for the synthesis of 2-substituted azulene derivatives.
View Article and Find Full Text PDFDesign, synthesis and biological activity of α-nitrile substituted guaiazulene-based chalcone derivatives.
Fitoterapia
October 2024
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, China. Electronic address:
In present study, seventeen α-nitrile substituted guaiazulene-based chalcone derivatives including twelve new were designed, synthesized, and assayed for antiviral, cytotoxicity and signal pathway activities. All derivatives showed potential antiviral activity towards influenza virus or herpes simplex virus (HSV), 7 g with the substitution of nitro group showed strong effects towards H1N1 virus at 30 μM with inhibitory rate of 66.0%, 7o with thiophene exhibited potent anti HSV-1 activities with inhibitory rate of 65.
View Article and Find Full Text PDFDesigning potentially singlet fission materials with an anti-Kasha behaviour.
Phys Chem Chem Phys
May 2024
Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, C/ Maria Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain.
Article Synopsis
- Singlet fission (SF) compounds have potential to enhance solar cell efficiency.
- Researchers used TD-DFT methods to design anti-Kasha azulene derivatives that can facilitate SF.
- Substituting azulenes with -OH (donor) and -CN (acceptor) groups shows improved SF characteristics compared to standard azulene, particularly with -CN on electrophilic carbons and -OH on nucleophilic carbons.
Persistent guaiazulene arylmethylium ions as electrophilic traps for metal enolates.
Chem Commun (Camb)
March 2024
Comenius University Bratislava, Faculty of Natural Sciences, Department of Organic Chemistry, Mlynská dolina, Ilkovičova 6, Bratislava 842 15, Slovakia.
Guaiazulene-stabilized cations reacted with metal enolates affording carbonyl compounds with an azulene moiety. Metal enolates generated by asymmetric conjugate addition of organometallic reagents led to enantioenriched products. Additionally, guaiazulene-substituted cations efficiently react with silyl enol ethers.
View Article and Find Full Text PDFUtilization of the through-space effect to design donor-acceptor systems of pyrrole, indole, isoindole, azulene and aniline.
Phys Chem Chem Phys
January 2024
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, Kerala, 695019, India.
Molecular electrostatic potential (MESP) topology analysis reveals the underlying phenomenon of the through-space effect (TSE), which imparts electron donor-acceptor properties to a wide range of chemical systems, including derivatives of pyrrole, indole, isoindole, azulene, and aniline. The TSE is inherent in pyrrole owing to the strong polarization of electron density (PoED) from the formally positively charged N-center to the CC bonding region. The N → CC directional nature of the TSE has been effectively employed to design molecules with high electronic polarization, such as bipyrroles, polypyrroles, phenyl pyrroles, multi-pyrrolyl systems and N-doped nanographenes.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!