[3 + 3] Cycloaddition of Azides with in Situ Formed Azaoxyallyl Cations To Synthesize 1,2,3,4-Tetrazines.

Org Lett

State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy , China Pharmaceutical University, Nanjing 210009 , P. R. China.

Published: April 2018

A formal [3 + 3] cycloaddition reaction between azides and in situ formed azaoxyallyl cations has been realized. This reaction provided an efficient and practical pathway to synthesize 1,2,3,4-tetrazines in good yields under mild conditions. Biologically active molecules could also be well compatible, highlighting the potential value of this reaction.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.8b00280DOI Listing

Publication Analysis

Top Keywords

azides situ
8
situ formed
8
formed azaoxyallyl
8
azaoxyallyl cations
8
synthesize 1234-tetrazines
8
cycloaddition azides
4
cations synthesize
4
1234-tetrazines formal
4
formal cycloaddition
4
cycloaddition reaction
4

Similar Publications

Rapid Crystallization and Versatile Metalation of Acetylhydrazone-Linked Covalent Organic Frameworks for Heterogenous Catalysis.

J Am Chem Soc

January 2025

School of Physical Science and Technology, Shanghai Key Laboratory of High-Resolution Electron Microscopy, State Key Laboratory of Advanced Medical Materials and Devices, ShanghaiTech University, Shanghai 201210, China.

Covalent organic frameworks (COFs) hold promise in heterogeneous metal catalysis benefiting from their robust, crystalline, and porous structures. However, synthetic challenges persist in prolonged crystallization times, limited metal loading, and uncertain coordination environments. Here, we present the rapid crystallization and versatile metalation of new acetylhydrazone-linked COFs (AH-COFs) by condensation of ketone and hydrazide components, featuring full conversion within 30 min under open-air and mild conditions.

View Article and Find Full Text PDF

Continuous Flow Chemistry and Bayesian Optimization for Polymer-Functionalized Carbon Nanotube-Based Chemiresistive Methane Sensors.

ACS Appl Mater Interfaces

December 2024

Materials and Manufacturing Directorate, Air Force Research Laboratory, Wright-Patterson AFB, Ohio 45433, United States.

We report the preparation of poly(ionic) polymer-wrapped single-walled carbon nanotube dispersions for chemiresistive methane (CH) sensors with improved humidity tolerance. Single-walled CNTs (SWCNTs) were noncovalently functionalized by poly(4-vinylpyridine) (P4VP) with varied amounts of a poly(ethylene glycol) (PEG) moiety bearing a Br and terminal azide group (Br-R). The quaternization of P4VP with Br-R was performed using continuous flow chemistry and Bayesian optimization-guided reaction selection.

View Article and Find Full Text PDF

We report the development of an azanide (NH) surrogate which enables the facile conversion of electron-deficient (hetero)aryl halides into primary N-aryl amines under transition-metal-free conditions. The designed amidine reagent is easy to prepare, bench stable, and undergoes facile N-arylation under basic conditions at 40 °C. Intermediate N-aryl amidines are readily cleaved to form N-aryl amines in situ through hydrolysis or base-promoted elimination.

View Article and Find Full Text PDF

Herein, an ultrasensitive electrochemical biosensor is constructed to detect mecA gene by utilizing electrochemically controlled atom transfer radical polymerization (eATRP) triggered by copper nanoflowers enriched on DNA polymers. Firstly, specific capture and enrichment of mecA gene is achieved by using magnetic separation system, effectively weakening the interference of the complex matrix. Next, enzyme-free hybridization chain reaction is triggered in the presence of mecA gene to form long DNA polymers containing numerous active sites for subsequent binding to streptavidin-copper hybrid nanoflowers (SA@Cu HNFs).

View Article and Find Full Text PDF

Carbonyl azides are important precursors to isocyanates and are used as energetic compounds. However, the further development of these compounds is limited by their inherently poor stability. In this study, we present a new family of carbonyl azides, 5-nitro-1H-1,2,4-triazol-3-yl-carbamoyl-azide (NTCA), which was synthesized through in situ oxidation cleavage of amino-tetrazole.

View Article and Find Full Text PDF

Want 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!