AI Article Synopsis
- A new method for creating furfuryl triazoles from furfuryl azides through a process called dearomative dimerization is presented.
- The reaction, which is facilitated by Lewis acid, leads to the formation of a furfuryl cation that engages in a unique cycloaddition and ring-opening sequence with another azide.
- By increasing the reaction time, these furfuryl triazoles can break down into 1-triazoles, and it's also possible to selectively combine furfuryl azides with benzyl azide.
Article Abstract
A dearomative dimerization of furfuryl azides for the construction of furfuryl triazoles is developed. As a rare leaving group, azide is capable of initiating the generation of a furfuryl cation under the Lewis acid-catalyzed conditions, followed by reacting with the other azide to realize an intermolecular [3 + 2] cycloaddition/furan ring-opening cascade. By extending the reaction time, a fragmentation reaction of resulting furfuryl triazoles occurs to afford 1-triazoles in high yield. Control studies demonstrated that key furfuryl cations also can be obtained from furfuryl triazoles. Furthermore, a chemoselective cross-cycloaddition can be achieved between furfuryl azides and a benzyl azide.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.2c01118 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Furan Dearomatization: A Route to Diverse Fluoroalkyl/Aryl Triazoles.
J Org Chem
April 2024
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
Article Synopsis
- The study focuses on synthesizing 5-fluoroalkyl-1,2,3-triazoles, important in medicinal chemistry.
- A furan dearomatization reaction is developed that uses a unique cationic intermediate for the synthesis of various triazoles.
- This method is notable for not requiring metal catalysts, showing great substrate tolerance and synthetic versatility.
Dual Roles of Azide: Dearomative Dimerization of Furfuryl Azides.
J Org Chem
August 2022
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
Article Synopsis
- A new method for creating furfuryl triazoles from furfuryl azides through a process called dearomative dimerization is presented.
- The reaction, which is facilitated by Lewis acid, leads to the formation of a furfuryl cation that engages in a unique cycloaddition and ring-opening sequence with another azide.
- By increasing the reaction time, these furfuryl triazoles can break down into 1-triazoles, and it's also possible to selectively combine furfuryl azides with benzyl azide.
The construction of phosphonate triazolyl by copper(II)-catalyzed furan dearomatized [3 + 2] cycloaddition.
Org Biomol Chem
August 2022
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
Triazole phosphonates are valuable structural motifs in chemical biology and the subject of growing recent interest. A novel methodology to synthesize triazolyl phosphonates starting from furfuryl phosphonate alcohols and organo-azides was developed. This method involved an intermolecular copper-catalyzed dearomatized [3 + 2] cycloaddition/furan ring-opening cascade reaction.
View Article and Find Full Text PDFCan the commonly used quenching method really evaluate the role of reactive oxygen species in pollutant abatement during catalytic ozonation?
Water Res
May 2022
School of Environment, Beijing Key Laboratory for Emerging Organic Contaminants Control, State Key Joint Laboratory of Environmental Simulation and Pollution Control, Tsinghua University, Beijing 100084 China. Electronic address:
Reactive oxygen species (ROS) such as hydroxyl radicals (•OH), superoxide radicals (O), and singlet oxygen (O) have often been suggested to play a role in ozone-resistant pollutant abatement during catalytic ozonation. However, there are significant controversies regarding their relative importance in literature. Currently, the role of ROS in pollutant abatement is commonly evaluated by the quenching method based on the assumption that the added ROS quenchers (e.
View Article and Find Full Text PDFYtterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles.
Org Lett
July 2020
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf) and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.
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!